(S)-(-)-Beta-N-乙酰基-丝氨酸乙酯 | 343335-40-0

• 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: (S)-(-)-Beta-N-乙酰基-丝氨酸乙酯
• 中文别名: (3S)-3-(乙酰氨基)戊酸乙酯
• 英文名称: ethyl (S)-3-acetamidopentanoate
• 英文别名: ethyl (3S)-3-acetamidopentanoate
• CAS: 343335-40-0
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: UOLLPCFHFWQWNU-QMMMGPOBSA-N

物化性质

• 密度：
  1.001

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-Beta-N-乙酰基-丝氨酸乙酯 在 盐酸 作用下， 反应 1.0h， 生成 (S)-3-氨基戊酸
  参考文献：
  名称：

  Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A

  摘要：

  The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00002-7
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 [Rh((S,S)-Me-BDPMI)(COD))BF₄] 吡啶 、 ammonium acetate 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.36 kPa 条件下， 反应 84.0h， 生成 (S)-(-)-Beta-N-乙酰基-丝氨酸乙酯
  参考文献：
  名称：

  Rh(I)-Catalyzed Enantioselective Hydrogenation of (E)- and (Z)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions

  摘要：

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.

  DOI：

  10.1021/ol0261884

文献信息

• Rh(I)-Catalyzed Enantioselective Hydrogenation of (<i>E</i>)- and (<i>Z</i>)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions
  作者：Sang-gi Lee、Yong Jian Zhang

  DOI：10.1021/ol0261884

  日期：2002.7.1

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.
• Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A
  作者：Szilvia Gedey、Arto Liljeblad、László Lázár、Ferenc Fülöp、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(01)00002-7

  日期：2001.2

  The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.