64318-28-1 4-羟基苯乙基氨基甲酸叔丁酯

中文名称: 4-羟基苯乙基氨基甲酸叔丁酯
英文名称: tert-Butyl 4-hydroxyphenethylcarbamate
CAS号

词条详情加载中…

名称和标识

中文名: 4-羟基苯乙基氨基甲酸叔丁酯
英文名: tert-Butyl 4-hydroxyphenethylcarbamate
CAS号: 64318-28-1
分子式: C13H19NO3
分子量: 237.29
中文别名: N-Boc-酪胺; [2-(4-羟基苯基)乙基]氨基甲酸叔丁酯; N-(叔丁氧羰基)酪胺; N-BOC-2-(4-羟苯基)乙胺; [2-(4-羟苯基)乙基]氨基甲酸T-丁酯; BOC-酪胺; N-(叔丁氧基羰基)-4-羟基苯乙胺; N-Boc-4-羟基苯乙胺
英文别名: N-Boc-tyramine; N-Boc-2-(4-hydroxyphenyl)ethylamine; [2-(4-HYDROXY-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER; N-(tert-Butoxycarbonyl)tyramine; 4-[2-(N-tert-ButoxycarbonylaMino)ethyl]phenol; N-[2-(4-Hydroxyphenyl)ethyl]carbaMic Acid 1,1-DiMethylethyl Ester; tert-butyl N-[2-(4-hydroxyphenyl)ethyl]carbamate; tert-Butyl [2-(4-hydroxyphenyl)ethyl]carbamate; Carbamic acid, N-[2-(4-hydroxyphenyl)ethyl]-, 1,1-dimethylethyl ester; N-t-Boc-tyramine; 4-[2-(tert-butyloxycarbonylamino)ethyl]phenol; 2-Methyl-2-propanyl [2-(4-hydroxyphenyl)ethyl]carbamate; N-(t-butoxycarbonyl)-2-(4-hydroxyphenyl)-ethylamine; 2-(4-hydroxyphenyl)ethylcarbamic acid,t-butyl ester

物化属性

LogP: 2.57
MLOGP: 2.07
SILICOS-IT LogP: 1.96
WLOGP: 2.46
XLOGP3: 2.53
XLogP3-AA

安全信息

安全说明

危险性质：非危险化学品

生产及用途

用途与制备

化学合成。

化学合成

合成路线 1（1. 合成：64318-28-1）

产率：73% 合成条件：Stage #1: With sodium hydroxide In 1,4-dioxane; Al 2 O 3 ; water for 0.17 h; Stage #2: at 20℃; Inert atmosphere Stage #3: With hydrogenchloride In water; ethyl acetate 实验步骤：a）N-（叔丁氧基羰基）-2-（4-羟基苯基） - 乙胺的合成将盐酸盐酸盐（1.0g; 5.76mmol; 1eq。）溶于二恶烷和蒸馏水（25 / 12mL）的混合物中，然后加入NaOH（0.46g; 11.5mmol）在10mL蒸馏水中的溶液。将全部搅拌10分钟，然后加入二叔丁基碳酸氢盐（Boc 2 O）（1.26g; 5.76mmol; 2当量。在氩气和环境温度下将反应物搅拌过夜。蒸发二恶烷后，向残留的水相中加入40mL EtOAc，用1M的1M水溶液将混合物的pH降至7-8。然后分离各相，水相用EtOAc（2×15mL）洗涤。然后将合并的有机相用Na 2 SO 4干燥，过滤并蒸发。然后在色谱柱（Al 2 O 3，CH 2 Cl 2）中纯化粗产物。 / Hex，85：15）得到N-（叔丁氧基羰基）-2-（4-羟基苯基） - 乙胺（0.98g; 73％）.Mp：61-62℃.IR（KBr）：3378.9（-OH） ; -CONH-）1686.6（CO ）。UV-Vis（CH 2 Cl 2）：277（1803）.1 H-NMR（400MHz，CDCl 3）：1.441（s，9H，10）; 2.703（t，J = 7.9Hz; 2H，CH2CH2N）; 3.329（m，2H，CH2CH2N）; 4.602（宽s，1H，NH或OH）; 6.023（宽s，1H，NH或OH）; 6.774（d，J = 8.3Hz; 2H; ArH）; 7.013（d，J = 8.3Hz; 2H; ArH）.13C-NMR（100MHz，CDCl3）：28.84（CMe3）; 35.64（CH2CH2N）; 42.49（CH2CH2N）; 80.15（CMe3）; 115.97（Cm）; 130.18（公司）; 130.50（Cp）; 155.38（Cipso）; 156.84（CO）.C13H19O3N的计算的初步分析（237.29）：C，65.80％; H，8.07％; N，5.90％;发现：C，65.77％; H，8.09％; N，5.90％.IE MS：181 [M-（Me）3CO-H + Na] +; 107 [M-（Me）3COC（O）NHCH2] 参考文献：

[1] Synthesis, 2009, # 22, p. 3838 - 3842 [2] Angewandte Chemie - International Edition, 2014, vol. 53, # 23, p. 5877 - 5881 [3] Angew. Chem., 2014, vol. 126, # 23, p. 5987 - 5991,5 [4] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 3, p. 633 - 639 [5] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 15, p. 5496 - 5509 [6] Patent: US2011/184070, 2011, A1. Location in patent: Page/Page column 17 [7] Journal of Pharmacology and Experimental Therapeutics, 2000, vol. 292, # 3, p. 1135 - 1145 [8] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6303 - 6312 [9] Patent: US5840726, 1998, A

[1] Patent: WO2006/73366, 2006, A1. Location in patent: Page/Page column 182 [2] Patent: WO2005/12296, 2005, A1. Location in patent: Page/Page column 185 [3] Patent: US5594004, 1997, A [4] Patent: WO2008/46598, 2008, A1. Location in patent: Page/Page column 96 [5] Patent: WO2009/68177, 2009, A1. Location in patent: Page/Page column 23 [6] Patent: WO2014/95920, 2014, A1. Location in patent: Page/Page column 63; 64 [7] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 12, p. 855 - 871 [8] Patent: US6375926, 2002, B1 [9] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 9, p. 1362 - 1363 [10] Synthesis, 2009, # 22, p. 3838 - 3842 [11] Asian Journal of Chemistry, 2017, vol. 29, # 6, p. 1313 - 1316 [12] ACS Chemical Neuroscience, 2017, vol. 8, # 7, p. 1530 - 1542 [13] Journal of Organic Chemistry, 1988, vol. 53, # 3, p. 487 - 499 [14] Patent: WO2007/8037, 2007, A1. Location in patent: Page/Page column 71-72 [15] Organic and Biomolecular Chemistry, 2012, vol. 10, # 14, p. 2798 - 2806,9 [16] Organic and Biomolecular Chemistry, 2012, vol. 10, # 14, p. 2798 - 2806 [17] Patent: WO2013/6734, 2013, A1. Location in patent: Paragraph 00578; 00579 [18] Patent: WO2017/102014, 2017, A1. Location in patent: Page/Page column 27 [19] Organic Process Research and Development, 2007, vol. 11, # 3, p. 598 - 604 [20] Patent: CN104829593, 2017, B. Location in patent: Paragraph 0062; 0151; 0152; 0153 [21] Tetrahedron, 2009, vol. 65, # 8, p. 1618 - 1629 [22] Journal of Organic Chemistry, 1984, vol. 49, # 6, p. 1013 - 1021 [23] Tetrahedron Letters, 2011, vol. 52, # 28, p. 3551 - 3554 [24] Patent: CN105585571, 2016, A. Location in patent: Paragraph 0032 [25] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1101 - 1112 [26] Patent: WO2004/26305, 2004, A1. Location in patent: Page/Page column 77 [27] Patent: WO2015/138895, 2015, A1. Location in patent: Paragraph 000343 [28] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1577 - 1583 [29] Chemistry - A European Journal, 2014, vol. 20, # 51, p. 17168 - 17177 [30] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738 [31] Patent: EP2913325, 2015, A1. Location in patent: Paragraph 0467; 0468 [32] Patent: CN105218557, 2016, A. Location in patent: Paragraph 0190; 0191; 0192 [33] Patent: CN106279040, 2017, A. Location in patent: Paragraph 0693; 0694; 0695 [34] Patent: CN104206385, 2017, B. Location in patent: Paragraph 0257; 0258; 0259; 0260 [35] Patent: CN104292169, 2018, B. Location in patent: Paragraph 0471; 0472; 0473 [36] Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 3, p. 341 - 349 [37] Khim. Geterotsikl. Soedin., 2017, vol. 53, # 3, p. 341 - 349,9 [38] Patent: US2009/69430, 2009, A1. Location in patent: Page/Page column 14; 18-19 [39] Patent: EP1798220, 2007, A1. Location in patent: Page/Page column 10-11 [40] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5539 - 5544 [41] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5349 - 5352 [42] Patent: EP1174421, 2002, A1. Location in patent: Page 11-12 [43] Patent: US6437146, 2002, B1 [44] Patent: US5874436, 1999, A [45] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1304 - 1307 [46] Chemistry - A European Journal, 2008, vol. 14, # 31, p. 9613 - 9619 [47] Patent: US2003/232788, 2003, A1. Location in patent: Page 14 [48] Patent: WO2004/20415, 2004, A1. Location in patent: Page 58-59 [49] Patent: WO2005/92836, 2005, A1. Location in patent: Page/Page column 20; 45-46 [50] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 52 - 55 [51] Chemical Communications, 2009, # 28, p. 4188 - 4190 [52] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 445 - 449 [53] Patent: US2012/46467, 2012, A1. Location in patent: Page/Page column 60; 61 [54] Tetrahedron, 2013, vol. 69, # 1, p. 242 - 256 [55] Patent: US2013/237524, 2013, A1. Location in patent: Paragraph 0224 [56] Chemistry--A European Journal, 2014, vol. 20, # 35, p. 11120 - 11128,9 [57] Organic and Biomolecular Chemistry, 2015, vol. 13, # 8, p. 2293 - 2299 [58] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854 [59] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0313 [60] Patent: US9149540, 2015, B2. Location in patent: Page/Page column 12 [61] Organic and Biomolecular Chemistry, 2016, vol. 14, # 40, p. 9490 - 9500 [62] Patent: US9522908, 2016, B2. Location in patent: Page/Page column 56 [63] Biochemical and Biophysical Research Communications, 2017, vol. 486, # 2, p. 314 - 320 [64] Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9331 - 9351 [65] Patent: US2018/230123, 2018, A1. Location in patent: Paragraph 0619-0620

64318-28-1 4-羟基苯乙基氨基甲酸叔丁酯 - 化工 AI 网