(S)-4-Benzyl-3-cinnamoyl-2,2,5,5-tetramethyloxazolidine | 1027188-98-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-4-Benzyl-3-cinnamoyl-2,2,5,5-tetramethyloxazolidine
• 英文别名: (E)-1-[(4S)-4-benzyl-2,2,5,5-tetramethyl-1,3-oxazolidin-3-yl]-3-phenylprop-2-en-1-one
• CAS: 1027188-98-2
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: QWXDHMGTZLCIKQ-APHAIJBRSA-N

物化性质

• 沸点：
  506.4±49.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyl-3-cinnamoyl-2,2,5,5-tetramethyloxazolidine 以84%的产率得到
  参考文献：
  名称：

  Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro, J. Org. Chem, 59 (1994) N 23, S 6949-6954

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-3-amino-2-methyl-4-phenylbutan-2-ol 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 (S)-4-Benzyl-3-cinnamoyl-2,2,5,5-tetramethyloxazolidine
  参考文献：
  名称：

  Effective Enantiocontrol in Conjugate Additions of Organocuprates. Highly Selective 1,5-Chiral Induction in the Conjugate Additions of Cuprates to .alpha.,.beta.-Unsaturated Amide Derivatives of 2,2-Dimethyloxazolidine Chiral Auxiliaries

  摘要：

  alpha,beta-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph(2)CuMgBr.MgBrI is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,pi* type charge transfer complexes.

  DOI：

  10.1021/jo00102a018

文献信息

• Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro, J. Org. Chem, 59 (1994) N 23, S 6949-6954
  作者：Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro

  DOI：——

  日期：——
• Effective Enantiocontrol in Conjugate Additions of Organocuprates. Highly Selective 1,5-Chiral Induction in the Conjugate Additions of Cuprates to .alpha.,.beta.-Unsaturated Amide Derivatives of 2,2-Dimethyloxazolidine Chiral Auxiliaries
  作者：Shuji Kanemasa、Hiroyuki Suenaga、Kenjiro Onimura

  DOI：10.1021/jo00102a018

  日期：1994.11

  alpha,beta-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph(2)CuMgBr.MgBrI is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,pi* type charge transfer complexes.