(S)-Isochroman-1-carboxylic acid methyl ester | 302347-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-Isochroman-1-carboxylic acid methyl ester
• 英文别名: methyl (1S)-3,4-dihydro-1H-isochromene-1-carboxylate
• CAS: 302347-64-4
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QKIMVWLIPIOCJO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-Isochroman-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 生成
  参考文献：
  名称：

  External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan

  摘要：

  Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01028-5
• 作为产物：
  描述：

  异色满 、 二氧化碳 、 三甲基硅烷化重氮甲烷 在 叔丁基锂 、 (4S,4′S)-(-)-2,2′-(3-戊烯基)双(4-异丙基噁唑啉) 作用下， 以 正己烷 为溶剂， 反应 2.5h， 生成 (S)-Isochroman-1-carboxylic acid methyl ester 、 (R)-Isochroman-1-carboxylic acid methyl ester
  参考文献：
  名称：

  External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan

  摘要：

  Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01028-5