(+)-jamtine | 111261-78-0

• 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
• 英文别名: Jamtine；methyl (12aS,12bS)-2,3-dimethoxy-6,8,10,11,12,12b-hexahydro-5H-isoindolo[1,2-a]isoquinoline-12a-carboxylate
• CAS: 111261-78-0
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: OMJBNEAAPLIXDX-ICSRJNTNSA-N

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：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-jamtine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到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 、 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 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
  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

• Syntheses of cis- and trans-Jamtine and Their N-Oxides via a Benzyl Configuration-Inversion Approach
  作者：Huaiji Zheng、Zhigang Liu、Zhengshen Wang、Yujie Li、Qiang Zhang、Jin-Ming Gao

  DOI：10.1055/s-0037-1610745

  日期：2020.3

  an oxidation/reduction approach. The N-oxide derivatives of the jamtine isomers were also synthesized and identified by X-ray crystallographic analysis. Additionally, a density functional theory calculation for the four possible N-oxide structures was exploited to gain further insight into the structure of the natural product in comparison to those of the synthetic N-oxides, because the NMR data of

  报道了四氢异喹啉生物碱果酱及其差向异构体的新合成。合成策略取决于一锅共轭还原/罗宾逊环化序列和通过氧化/还原方法进行的有效苄基构型反转。Jamtine 异构体的 N-氧化物衍生物也被合成并通过 X 射线晶体学分析进行鉴定。此外，利用四种可能的 N-氧化物结构的密度泛函理论计算，与合成 N-氧化物的结构相比，进一步深入了解天然产物的结构，因为合成衍生物的 NMR 数据不匹配那些报告的天然果酱 N-氧化物。
• 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：——
• 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：——
• 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.