((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid ethyl ester | 117155-95-0

• 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
• 英文名称: ((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid ethyl ester
• 英文别名: ethyl N-[(2S)-1-chloro-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 117155-95-0
• 化学式: C₁₂H₁₄ClNO₃
• 分子量: 255.701
• InChiKey: NAQVWCZKERTFHG-JTQLQIEISA-N

物化性质

• 沸点：
  390.7±42.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid ethyl ester 在 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 trans-(1S,2S)-1-ethyl-2-[(N-ethoxycarbonyl)amino]-1-indanol
  参考文献：
  名称：

  trans-(1S,2S)-1-Substituted-2-(N,N-dialkylamino)-1-indanol derivatives as chiral ligands in the catalytic enantioselective addition of diethylzinc to aldehydes

  摘要：

  A series of optically active trans-(1S,2S)-1-substituted-2-(N,N-dialkylamino)-1-indanol derivatives 1-6 were synthesized and applied in the catalytic enantioselective addition of dicthylzinc to aldehydes. The enantiomeric purity of the addition products increased considerably with increasing bulk of the substituents both on the nitrogen atom and the hydroxy-bearing carbon atom of the ligands. sec-Alcohols were obtained in good yields with enantiomeric excesses tip to 93.1%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00183-0
• 作为产物：
  描述：

  N-乙氧羰基-L-苯丙氨酸 在 五氯化磷 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 ((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid ethyl ester
  参考文献：
  名称：

  钯催化的非手性烯磺酰胺中间体对N-磺酰基氨基醇的不对称氢解

  摘要：

  完全控制猫的行为：在手性Pd催化剂和三氟乙酸（TFA）存在下，对N-磺酰基氨基醇进行立体收敛正式氢解，得到具有两个连续立体中心的手性胺（参见方案； TFE =三氟乙醇，Ts =对甲苯磺酰基） 。通过酸催化的脱水反应可生成高达94％  ee的产物，从而得到烯磺酰胺，烯胺/亚胺异构化和Pd催化的不对称氢化反应。

  DOI：

  10.1002/anie.201307036

文献信息

• trans-(1S,2S)-1-Substituted-2-(N,N-dialkylamino)-1-indanol derivatives as chiral ligands in the catalytic enantioselective addition of diethylzinc to aldehydes
  作者：Qianyong Xu、Hongfang Yang、Xinfu Pan、Albert S.C. Chan

  DOI：10.1016/s0957-4166(02)00183-0

  日期：2002.6

  A series of optically active trans-(1S,2S)-1-substituted-2-(N,N-dialkylamino)-1-indanol derivatives 1-6 were synthesized and applied in the catalytic enantioselective addition of dicthylzinc to aldehydes. The enantiomeric purity of the addition products increased considerably with increasing bulk of the substituents both on the nitrogen atom and the hydroxy-bearing carbon atom of the ligands. sec-Alcohols were obtained in good yields with enantiomeric excesses tip to 93.1%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Asymmetric Hydrogenolysis of<i>N</i>-Sulfonyl Aminoalcohols via Achiral Enesulfonamide Intermediates
  作者：Chang-Bin Yu、Yong-Gui Zhou

  DOI：10.1002/anie.201307036

  日期：2013.12.9

  stereoconvergent formal hydrogenolysis of N‐sulfonyl aminoalcohols in the presence of a chiral Pd catalyst and trifluoroacetic acid (TFA) gave chiral amines with two contiguous stereocenters (see scheme; TFE=trifluoroethanol, Ts=p‐tosyl). The products were formed with up to 94 % ee by acid‐catalyzed dehydration to afford an enesulfonamide, enamine/imine isomerization, and Pd‐catalyzed asymmetric hydrogenation

  完全控制猫的行为：在手性Pd催化剂和三氟乙酸（TFA）存在下，对N-磺酰基氨基醇进行立体收敛正式氢解，得到具有两个连续立体中心的手性胺（参见方案； TFE =三氟乙醇，Ts =对甲苯磺酰基） 。通过酸催化的脱水反应可生成高达94％  ee的产物，从而得到烯磺酰胺，烯胺/亚胺异构化和Pd催化的不对称氢化反应。