[(3S)-3,4,4-trimethyl-2-oxooxolan-3-yl] (2S)-2-(1,3-dioxoisoindol-2-yl)propanoate | 272449-22-6

• 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: [(3S)-3,4,4-trimethyl-2-oxooxolan-3-yl] (2S)-2-(1,3-dioxoisoindol-2-yl)propanoate
• CAS: 272449-22-6
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: DMIXXPSMGHNFEH-XTZNXHDOSA-N

物化性质

• 沸点：
  497.8±40.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S)-3,4,4-trimethyl-2-oxooxolan-3-yl] (2S)-2-(1,3-dioxoisoindol-2-yl)propanoate 在 acid 作用下， 生成 L-丙氨酸
  参考文献：
  名称：

  Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary

  摘要：

  A dynamic kinetic resolution of racemic N-phthalyl amino acids by stereoselective esterification was examined using (S)-alpha-methylpantolactone as the chiral auxiliary. The reaction of various racemic N-phthalyl amino acids with this chiral alcohol in the presence of both DCC and DMAP afforded predominantly the (S,S)-esters in nearly quantitative yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00017-3
• 作为产物：
  描述：

  (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 [(3S)-3,4,4-trimethyl-2-oxooxolan-3-yl] (2S)-2-(1,3-dioxoisoindol-2-yl)propanoate
  参考文献：
  名称：

  Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary

  摘要：

  A dynamic kinetic resolution of racemic N-phthalyl amino acids by stereoselective esterification was examined using (S)-alpha-methylpantolactone as the chiral auxiliary. The reaction of various racemic N-phthalyl amino acids with this chiral alcohol in the presence of both DCC and DMAP afforded predominantly the (S,S)-esters in nearly quantitative yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00017-3

文献信息

• Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary
  作者：Monique Calmes、Christèle Glot、Thibaut Michel、Marc Rolland、Jean Martinez

  DOI：10.1016/s0957-4166(00)00017-3

  日期：2000.2

  A dynamic kinetic resolution of racemic N-phthalyl amino acids by stereoselective esterification was examined using (S)-alpha-methylpantolactone as the chiral auxiliary. The reaction of various racemic N-phthalyl amino acids with this chiral alcohol in the presence of both DCC and DMAP afforded predominantly the (S,S)-esters in nearly quantitative yield. (C) 2000 Elsevier Science Ltd. All rights reserved.