(S)-3-phenyl-2-<(S)-phenylethyl>butanoic acid | 219590-67-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-phenyl-2-<(S)-phenylethyl>butanoic acid
• 英文别名: (3S)-3-phenyl-2-[(1S)-1-phenylethyl]butanoic acid
• CAS: 219590-67-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: CDTPOBNEGFGCTF-ZIAGYGMSSA-N

物化性质

• 沸点：
  380.0±11.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-phenyl-2-<(S)-phenylethyl>butanoic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成 (S)-3-phenyl-2-[(S)-phenylethyl]butanoic acid chloride
  参考文献：
  名称：

  New Homochiral Ligands Bearing Nonstereogenic Chirotopic Centers. Lithiated N,N‘-Dialkylureas as Chiral Bases and Sterically Crowded Phosphines for Asymmetric Catalysis

  摘要：

  The synthesis of new homochiral pseudo-C-2-symmetrical ligands of type 1 bearing a nonstereogenic chirotopic center is reported. Two such structural units are combined in the ureas 2 and 10, which proved to be useful for enantioselective deprotonation and alkylation of ketones (up to 88% ee). The monophosphine 3 induced a high enantiomeric excess in the Pd-catalyzed allylation of dimethyl malonate (up to 73% ee). Furthermore, we have shown that the achiral sterically crowded alkyl diphosphine 23 efficiently stabilized Pd(0) at high temperatures.

  DOI：

  10.1021/jo990412u
• 作为产物：
  描述：

  (R)-(+)-1-苯基乙醇 在 溴 、 对甲苯磺酸 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 5.67h， 生成 (S)-3-phenyl-2-<(S)-phenylethyl>butanoic acid
  参考文献：
  名称：

  New Homochiral Ligands Bearing Nonstereogenic Chirotopic Centers. Lithiated N,N‘-Dialkylureas as Chiral Bases and Sterically Crowded Phosphines for Asymmetric Catalysis

  摘要：

  The synthesis of new homochiral pseudo-C-2-symmetrical ligands of type 1 bearing a nonstereogenic chirotopic center is reported. Two such structural units are combined in the ureas 2 and 10, which proved to be useful for enantioselective deprotonation and alkylation of ketones (up to 88% ee). The monophosphine 3 induced a high enantiomeric excess in the Pd-catalyzed allylation of dimethyl malonate (up to 73% ee). Furthermore, we have shown that the achiral sterically crowded alkyl diphosphine 23 efficiently stabilized Pd(0) at high temperatures.

  DOI：

  10.1021/jo990412u

文献信息

• New Chiral Ligands with Nonstereogenic Chirotopic Centers for Asymmetric Synthesis
  作者：Claus-Dieter Graf、Christophe Malan、Paul Knochel

  DOI：10.1002/(sici)1521-3773(19981116)37:21<3014::aid-anie3014>3.0.co;2-6

  日期：1998.11.16

  Pseudo-C2 -symmetrical ligands have been prepared efficiently: The attachment of the chiral alkyl group to the heteroatom (P or N) through a nonstereogenic, chirotopic carbon center facilitates their synthesis as the configuration at this carbon atom no longer needs to be controlled. Two such ligands were combined, for example, in the base 1, which is especially useful for asymmetric deprotonation of prochiral ketones [Eq. (a)].