(12aS,12bR)-8-oxo-5,8,11,12,12b-hexahydro-6H-isoindolo[1,2-a]isoquinoline-12a-carboxylic acid methyl ester | 501085-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (12aS,12bR)-8-oxo-5,8,11,12,12b-hexahydro-6H-isoindolo[1,2-a]isoquinoline-12a-carboxylic acid methyl ester
• 英文别名: methyl (12aS,12bS)-2,3-dimethoxy-8-oxo-5,6,10,11,12,12b-hexahydroisoindolo[1,2-a]isoquinoline-12a-carboxylate
• CAS: 501085-30-9
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: AOJOYTUAWIIYHP-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (12aS,12bR)-8-oxo-5,8,11,12,12b-hexahydro-6H-isoindolo[1,2-a]isoquinoline-12a-carboxylic acid methyl ester 在 2,6-二叔丁基-4-甲基吡啶 、 trimethoxonium tetrafluoroborate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 生成 jamtine N-oxide
  参考文献：
  名称：

  Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine

  摘要：

  The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.046
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 sodium tetrahydroborate 、 正丁基锂 、 chiral PhCH(Me)NLiCH(Ph)CH(Ph)NHCH(Me)Ph 、 二苯基二硒醚 、 camphor-10-sulfonic acid 、 potassium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (12aS,12bR)-8-oxo-5,8,11,12,12b-hexahydro-6H-isoindolo[1,2-a]isoquinoline-12a-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Proposed Structure of the Medicinal Alkaloid Jamtine Using the Chiral Base Approach

  摘要：

  [GRAPHICS]A highly step-economic asymmetric synthesis of the tetracyclic structure assigned to the medicinal alkaloid jamtine has been accomplished using a chiral lithium amide base desymmetrization of a ring-fused imide. The structure synthesized appears to be different from that of the natural product originally reported.

  DOI：

  10.1021/ol027447s