(S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one
• 英文别名: (S)-4-benzyl-3-propanoyloxazolidine；4-Benzyl-3-propionyl-1,3-oxazolidine；1-[(4S)-4-benzyl-1,3-oxazolidin-3-yl]propan-1-one
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: PYBXDAADXDXNEB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  巴豆酸甲酯 、 (S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以96%的产率得到(S)-4-benzyl-3-(4-methoxycarbonyl-2,3-dimethylbutanoyl)oxazolidine
  参考文献：
  名称：

  High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters

  摘要：

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.

  DOI：

  10.1016/0040-4020(95)00623-g
• 作为产物：
  描述：

  聚合甲醛 、 (S)-3-phenyl-2-propanamido-1-propanol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以60%的产率得到(S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one
  参考文献：
  名称：

  High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters

  摘要：

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.

  DOI：

  10.1016/0040-4020(95)00623-g

文献信息

• Carbohydrate-based first stereoselective total synthesis of bioactive cytospolide P
  作者：Pathi Suman、Bhimapaka China Raju

  DOI：10.1039/c4ob00323c

  日期：——

  A facile stereoselective approach has been developed for the total synthesis of cytospolide P via Yamaguchi macrolactonization.

  已开发出一种简便的立体选择性方法，用于通过Yamaguchi环内酯化合成细胞孢内酯P的全合成。
• High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters
  作者：Shuji Kanemasa、Masafumi Nomura、Sachiyo Yoshinaga、Hidetoshi Yamamoto

  DOI：10.1016/0040-4020(95)00623-g

  日期：1995.9

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.