jamtine N-oxide | 111261-79-1

• 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: jamtine N-oxide
• 英文别名: methyl (12aS,12bS)-2,3-dimethoxy-7-oxido-6,8,10,11,12,12b-hexahydro-5H-isoindolo[1,2-a]isoquinolin-7-ium-12a-carboxylate
• CAS: 111261-79-1
• 化学式: C₂₀H₂₅NO₅
• 分子量: 359.422
• InChiKey: LXHLCKTUQQZKAL-WZENJKSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  jamtine N-oxide 在 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (+)-jamtine
  参考文献：
  名称：

  Ahmad, Viqar Uddin; Atta-ur-Rahman; Rasheed, Tahir, Heterocycles, 1987, vol. 26, # 5, p. 1251 - 1255

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 sodium tetrahydroborate 、 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 、 chiral PhCH(Me)NLiCH(Ph)CH(Ph)NHCH(Me)Ph 、 二苯基二硒醚 、 camphor-10-sulfonic acid 、 trimethoxonium tetrafluoroborate 、 potassium hydride 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 jamtine N-oxide
  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

文献信息

• Asymmetric Total Synthesis of the Proposed Structure of the Medicinal Alkaloid Jamtine Using the Chiral Base Approach
  作者：Nigel S. Simpkins、Christopher D. Gill

  DOI：10.1021/ol027447s

  日期：2003.2.1

  [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.
• AHMAD, VIGAR UDDIN;RAHMAN, ATTA-UR;RASHEED, TAHIR;REHMAN, HABIB-UR, HETEROCYCLES, 26,(1987) N 5, 1251-1255
  作者：AHMAD, VIGAR UDDIN、RAHMAN, ATTA-UR、RASHEED, TAHIR、REHMAN, HABIB-UR

  DOI：——

  日期：——
• Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine
  作者：Christopher D Gill、Daniel A Greenhalgh、Nigel S Simpkins

  DOI：10.1016/j.tet.2003.08.046

  日期：2003.11

  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.
• Ahmad, Viqar Uddin; Atta-ur-Rahman; Rasheed, Tahir, Heterocycles, 1987, vol. 26, # 5, p. 1251 - 1255
  作者：Ahmad, Viqar Uddin、Atta-ur-Rahman、Rasheed, Tahir、Habib-ur-Rehman

  DOI：——

  日期：——