11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]-indole | 13233-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]-indole
• 英文别名: (+/-)-11-methylharmicine；11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole；2,3,5,6,11,11b-hexahydro-11-methyl-1H-indolizino[8,7-b]indole；2,3,5,6,11,11b-Hexahydro-11-methyl-1H-indolo<3,2-g>indolizine；11-methyl-1,2,3,5,6,11b-hexahydroindolizino[8,7-b]indole
• CAS: 13233-43-7
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: UPXLNPGYFFCADO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]-indole 在 lithium 作用下， 以 乙酸乙酯 为溶剂， 生成 3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azonino[5,4-b]indole
  参考文献：
  名称：

  Indole fused heterocyclic diuretic compounds

  摘要：

  通过在液氨中使用锂对应的季铵碘化物盐进行裂解，制备了取代的1,2,4,5,6,7,8,9-八氢-3H-氮杂环[5,4-b]-吲哚和取代的1,2,3,4,5,6,7,8-八氢-氮杂环[5,4-b]-吲哚。这些产物具有利尿活性。

  公开号：

  US03943148A1
• 作为产物：
  描述：

  tert-butyl 9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 17.13h， 生成 11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]-indole
  参考文献：
  名称：

  Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation–Substitution

  摘要：

  A method to prepare 1-substituted N-Boc-tetrahydro-beta-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Bot group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.

  DOI：

  10.1021/acs.joc.5b00725

文献信息

• Polycyclic compounds as potent alpha2-adrenoceptor antagonists
  申请人：Din Belle David

  公开号：US20060094740A1

  公开（公告）日：2006-05-04

  A compound of formula 1, wherein X, Z, R 1 to R 10 , R 15 , R 16 , m, n, r and t are as defined in claim 1, or a pharmaceutically acceptable salt or ester thereof, useful as an alpha-2 antagonist. The compounds of formula I can be used for the treatment of diseases or conditions where antagonists of alpha-2 adrenoceptors are indicated to be effective.

  一种公式1的化合物，其中X，Z，R1至R10，R15，R16，m，n，r和t如权利要求1中所定义，或其药学上可接受的盐或酯，可用作α-2拮抗剂。公式I的化合物可用于治疗需要α-2肾上腺素能受体拮抗剂有效的疾病或情况。
• POLYCYCLIC COMPOUNDS AS POTENT ALPHA2-ADRENOCEPTOR ANTAGONISTS
  申请人：ORION CORPORATION

  公开号：EP1490361B1

  公开（公告）日：2007-10-03
• US3943148A
  申请人：——

  公开号：US3943148A

  公开（公告）日：1976-03-09
• US7592350B2
  申请人：——

  公开号：US7592350B2

  公开（公告）日：2009-09-22
• Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation–Substitution
  作者：Edward J. Cochrane、Lorraine A. Hassall、Iain Coldham

  DOI：10.1021/acs.joc.5b00725

  日期：2015.6.5

  A method to prepare 1-substituted N-Boc-tetrahydro-beta-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Bot group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.