(3S)-4-氨基-3-苯基丁酸盐酸盐 | 52950-37-5

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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
• 中文名称: (3S)-4-氨基-3-苯基丁酸盐酸盐
• 中文别名: (S)-4-氨基-3-苯基丁酸盐酸盐
• 英文名称: 4-amino-(3S)-3-phenyl-butyric acid hydrochloride
• 英文别名: (S)-3-phenyl-4-aminobutyric acid hydrochloride；(S)-3-carboxy-2-phenylpropan-1-aminium chloride；(S)-4-Amino-3-phenylbutanoic acid hydrochloride；(3S)-4-amino-3-phenylbutanoic acid;hydrochloride
• CAS: 52950-37-5
• 化学式: C₁₀H₁₃NO₂*ClH
• 分子量: 215.68
• InChiKey: XSYRYMGYPBGOPS-SBSPUUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-phenylpent-4-enoic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium azide 、 Pseudomonas cepacia lipase 、 18-冠醚-6 、 palladium on activated charcoal 、 氢气 、 sodium cyanoborohydride 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 136.83h， 生成 (3S)-4-氨基-3-苯基丁酸盐酸盐
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: the influence of donor of the alkoxy group on enantioselective esterification

  摘要：

  A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-gamma-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the racemic substrate provided products with good enantiselectivity upon esterification. In these reactions, a new class of alkoxy group donor-orthoesters, acetals and ketals were used. The best results of the enzymatic kinetic resolution were obtained for triethyl orthoacetate in toluene solvent. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.016

文献信息

• Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)−Diamine Complexes
  作者：David A. Evans、Shizue Mito、Daniel Seidel

  DOI：10.1021/ja0735913

  日期：2007.9.1

  Readily prepared Ni(II)-bis[(R,R)-N,N'-dibenzylcyclohexane-1,2-diamine]Br(2) was shown to catalyze the Michael addition of 1,3-dicarbonyl compounds to nitroalkenes at room temperature in good yields with high enantioselectivities. The two diamine ligands in this system each play a distinct role: one serves as a chiral ligand to provide stereoinduction in the addition step while the other functions

  容易制备的 Ni(II)-双[(R,R)-N,N'-二苄基环己烷-1,2-二胺]Br(2) 在室温下可催化 1,3-二羰基化合物与硝基烯烃的迈克尔加成反应温度高，产率高，对映选择性高。该系统中的两个二胺配体各自发挥不同的作用：一个作为手性配体在加成步骤中提供立体诱导，而另一个作为底物烯醇化的基础。还研究了催化剂内的配体改性，以促进脂肪族硝基烯烃、1,3-二酮和 β-酮酸的反应。Ni(II)-双[(R,R)-N,N'-di-p-bromo-benzylcyclohex-1,2-diamine]Br(2) 在这些情况下被发现是一种有效的催化剂。此外，单二胺络合物，Ni(II)-[(R,R)-N,N'-二苄基环己烷-1,2-二胺]Br(2)，在水存在下催化加成反应。所提出的立体化学诱导模型显示与 X 射线结构分析一致。
• Microbial desymmetrization of 3-arylglutaronitriles, an unusual enhancement of enantioselectivity in the presence of additives
  作者：Mei-Xiang Wang、Chu-Sheng Liu、Ji-Sheng Li、Otto Meth-Cohn

  DOI：10.1016/s0040-4039(00)01518-5

  日期：2000.10

  3-arylglutaronitriles catalyzed by Rhodococcus sp. AJ270 cells proceeded regiospecifically and enantioselectively to produce S-(+)-3-aryl-4-cyanobutyric acids in high enantiomeric excess. Convenient chemoenzymatic syntheses of optically active R-(−)-4-amino-3-phenylbutyric acid and 4R-(−)-4-phenyltetrahydropyran-2-one are described.

  在有机添加剂（例如丙酮或β-环糊精）的存在下，或在己烷和磷酸盐缓冲液的双相系统中，红球菌（Rhodococcus sp。）催化3-芳基戊二腈的微生物脱对称化。AJ270细胞在区域特异性和对映体选择性上产生高对映体过量的S -（+）-3-芳基-4-氰基丁酸。描述了光学活性R -（-）-4-氨基-3-苯基丁酸和4 R -（-）-4-苯基四氢吡喃-2-酮的便捷化学酶促合成。
• Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins
  作者：Oleg I. Afanasyev、Fedor S. Kliuev、Alexey A. Tsygankov、Yulia V. Nelyubina、Evgenii Gutsul、Valentin V. Novikov、Denis Chusov

  DOI：10.1021/acs.joc.2c01339

  日期：2022.9.16

  step-by-step increase in their complexity to improve efficiency. Herein we describe that simple in situ addition of the fluoride source to the asymmetric organometallic catalyst can improve not only activity but also enantioselectivity. Bromide–nickel diimine complexes were found to catalyze asymmetric Michael addition in low yields and ee, but activation with fluoride leads to a significant improvement

  如今，用于有机金属催化剂的新型手性配体的设计通常基于逐步增加其复杂性以提高效率。在这里，我们描述了将氟化物源简单地原位添加到不对称有机金属催化剂中，不仅可以提高活性，还可以提高对映选择性。发现溴化物-镍二亚胺配合物以低产率和 ee 催化不对称迈克尔加成，但用氟化物活化导致催化剂性能显着提高。开发的方法用于制备几种对映体富集的 GABA 类似物。
• SOBOCINSKA M.; ZOBACHEVA M. M.; PEREKALIN V. V.; KUPRYSZEWSKI G., POL. J. CHEM., 1979, 53, NO 2, 435-44)S
  作者：SOBOCINSKA M.、 ZOBACHEVA M. M.、 PEREKALIN V. V.、 KUPRYSZEWSKI G.

  DOI：——

  日期：——
• Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: the influence of donor of the alkoxy group on enantioselective esterification
  作者：Anna Brodzka、Dominik Koszelewski、Malgorzata Cwiklak、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2013.02.016

  日期：2013.4

  A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-gamma-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the racemic substrate provided products with good enantiselectivity upon esterification. In these reactions, a new class of alkoxy group donor-orthoesters, acetals and ketals were used. The best results of the enzymatic kinetic resolution were obtained for triethyl orthoacetate in toluene solvent. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.