(S)-2-[(2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester | 787620-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (S)-2-[(2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester
• CAS: 787620-60-4
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: JBOXQQKZILIMGL-FNNAPWSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester 在 KY zeolite 、 对甲氧基苯乙酮 作用下， 以 正己烷 为溶剂， 反应 1.5h， 生成 (S)-2-[((2R,3R)-2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester 、 (S)-2-[((2S,3S)-2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites

  摘要：

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

  DOI：

  10.1021/jo049365i
• 作为产物：
  描述：

  N-甲基-L-缬氨酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-2-[(2,3-Diphenyl-cyclopropanecarbonyl)-methyl-amino]-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites

  摘要：

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

  DOI：

  10.1021/jo049365i