ethyl (R)-3-amino-3-(2-thienyl)propanoate | 768356-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (R)-3-amino-3-(2-thienyl)propanoate
• 英文别名: Ethyl (3R)-3-amino-3-(thiophen-2-YL)propanoate；ethyl (3R)-3-amino-3-thiophen-2-ylpropanoate
• CAS: 768356-40-7
• 化学式: C₉H₁₃NO₂S
• 分子量: 199.274
• InChiKey: XYBONARLWNRZCA-SSDOTTSWSA-N

物化性质

• 沸点：
  305.5±32.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (R)-3-amino-3-(2-thienyl)propanoate 以 二丁醚 为溶剂， 反应 50.0h， 生成 (S)-3-Butyrylamino-3-thiophen-2-yl-propionic acid ethyl ester
  参考文献：
  名称：

  通过钯纳米催化剂和南极念珠菌脂肪酶 A 的多相系统动态拆分 β-氨基酯

  摘要：

  β-氨基酯的动态动力学拆分 (DKR) 已通过使用非均相外消旋化催化剂和接受芳香族、杂芳香族和脂肪族化合物的固定化酶开发出来。

  DOI：

  10.1002/ejoc.201001714
• 作为产物：
  描述：

  3-氨基-3-(2-噻吩基)丙酸 在 氯化亚砜 、 Candida antarctica Lipase A 作用下， 反应 0.5h， 生成 ethyl (R)-3-amino-3-(2-thienyl)propanoate
  参考文献：
  名称：

  Candida antarctica lipase A—a powerful catalyst for the resolution of heteroaromatic β-amino esters

  摘要：

  Enantioselective acylations of 3-amino-3-beteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar = 2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E > 100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00637-7

文献信息

• Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
  作者：Jianheng Ye、Chao Wang、Lin Chen、Xinjun Wu、Li Zhou、Jian Sun

  DOI：10.1002/adsc.201501061

  日期：2016.3.31

  reduction of N‐unsubstituted β‐enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N‐unsubstituted β‐enamino esters has been developed. Using N‐tert‐butylsulfinyl‐L‐proline‐derived amides and L‐pipecolinic acid‐derived formamides as catalyst, a broad range of β‐aryl‐ and β‐alkyl‐substituted

  N-未取代的β-烯胺酯的催化不对称还原是不对称催化的主要挑战。在本文中，开发了第一个可用于N-未取代的β-烯氨基酯不对称氢化硅烷化的有机催化体系。使用ñ -叔-butylsulfinyl-大号脯氨酸衍生的酰胺和大号-pipecolinic酸衍生甲酰胺作为催化剂，广泛β -芳基-和β-烷基取代的游离β氨基酯可以以高产率制备，并且对映选择性。（R）-3-氨基-3-苯基丙酸乙酯和异丙基（S）-3-氨基-4-（2,3,5-三氟苯基）丁酸酯。所得产品可以通过短合成途径顺利转化为FDA批准的药物达泊西汀和西他列汀。
• Burkholderia cepacia lipase is an excellent enzyme for the enantioselective hydrolysis of β-heteroaryl-β-amino esters
  作者：Gábor Tasnádi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2009.06.019

  日期：2009.8

  The enantioselective (E > 200) lipase PS-catalysed hydrolysis of beta-heteroaryl-beta-amino esters is described. The reactions were performed with H2O (0.5 equiv) in either diisopropyl ether or tert-butyl methyl ether at 25 degrees C. The resulting beta-heteroaryl-substituted beta-amino acid enantiomers were formed in high enantiomeric excess (ee >= 97%) and in good yield (>= 40%). (c) 2009 Elsevier Ltd. All rights reserved.
• Candida antarctica lipase A—a powerful catalyst for the resolution of heteroaromatic β-amino esters
  作者：Magdolna Solymár、Ferenc Fülöp、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(02)00637-7

  日期：2002.10

  Enantioselective acylations of 3-amino-3-beteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar = 2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E > 100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Dynamic Kinetic Resolution of β-Amino Esters by a Heterogeneous System of a Palladium Nanocatalyst and Candida antarctica Lipase A
  作者：Karin Engström、Mozaffar Shakeri、Jan-E. Bäckvall

  DOI：10.1002/ejoc.201001714

  日期：2011.4

  A dynamic kinetic resolution (DKR) of β-amino esters have been developed by the use of a heterogeneous racemization catalyst and an immobilized enzyme that accepts aromatic, heteroaromatic and alip ...

  β-氨基酯的动态动力学拆分 (DKR) 已通过使用非均相外消旋化催化剂和接受芳香族、杂芳香族和脂肪族化合物的固定化酶开发出来。