methyl 4-(bromomethyl)-hexanoate | 73805-44-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-(bromomethyl)-hexanoate
• 英文别名: methyl 4-(bromomethyl)hexanoate
• CAS: 73805-44-4
• 化学式: C₈H₁₅BrO₂
• 分子量: 223.11
• InChiKey: MXRDDZVSSRZBCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-(bromomethyl)-hexanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到4-(Bromomethyl)hexanal
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 5. Studies syntheses of .psi.-vincadifformine, 20-epi-.psi.-vincadifformine, pandoline, 20-epipandoline, and the C-16 epimeric(carbomethoxy)velbanamines

  摘要：

  DOI：

  10.1021/jo01304a023
• 作为产物：
  描述：

  甲基4-甲酰基己酸酯 在 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 methyl 4-(bromomethyl)-hexanoate
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 5. Studies syntheses of .psi.-vincadifformine, 20-epi-.psi.-vincadifformine, pandoline, 20-epipandoline, and the C-16 epimeric(carbomethoxy)velbanamines

  摘要：

  DOI：

  10.1021/jo01304a023

文献信息

• Preparation of vincadifformine and related derivatives
  申请人：University of Vermont

  公开号：US04283536A1

  公开（公告）日：1981-08-11

  This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties. A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give an alkyl 1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole 5-carboxylate (VIII). In an alternative embodiment, compound (VI) can be hydrogenated to the corresponding dialkyl 1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate which is then decarboxylated into compound (VIII). Compound (VIII) is condensed with a functionalised aldehyde, typically a epoxy aldehyde or a haloaldehyde such as 1-bromo-4-formylhexane, to give vincadifformine or similar pentacyclic derivatives.

  本发明涉及文卡地福明及其相关衍生物的制备，这些化合物可作为合成其他生物碱如文卡明等具有有趣的精神药理学特性的起始物质。首先将四氢-β-咔啉（II）与苯甲酰氯反应，得到2-苯甲酰基-1,2,3,4-四氢-9H-吡啶（3,4-b）-吲哚（III）。然后还原化合物（III）得到2-苄基-1,2,3,4-四氢-9H-吡啶（3,4-b）-吲哚（IV）。然后，将化合物（IV）转化为氯吲哚啉衍生物（V），并立即用金属二烷基丙二酸盐（如丁基甲基丙二酸铊）处理，得到双烷基-3-苄基-1,2,3,4,5,6-六氢氮杂环（4,5-b）-吲哚-5,5-二羧酸酯（VI）。化合物（VI）部分脱羧后得到烷基-3-苄基-1,2,3,4,5,6-六氢氮杂环（4,5-b）-吲哚-5-羧酸酯（VII）。化合物（VII）经过氢化后得到烷基-1,2,3,4,5,6-六氢氮杂环（4,5-b）-吲哚-5-羧酸酯（VIII）。在另一种实施方案中，化合物（VI）可以氢化为相应的双烷基-1,2,3,4,5,6-六氢氮杂环（4,5-b）-吲哚-5,5-二羧酸酯，然后脱羧为化合物（VIII）。化合物（VIII）与功能化醛（通常为环氧醛或卤代醛，如1-溴-4-甲酰己烷）缩合，得到文卡地福明或类似的五环衍生物。
• Process for the synthesis of vincadifformine and related derivatives
  申请人：Omnium Chimique Societe Anonyme

  公开号：US04267330A1

  公开（公告）日：1981-05-12

  This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties. A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.

  本发明涉及文卡地福明及其相关衍生物的制备，这些衍生物可用作合成文卡明和其他具有有趣的精神药理学性质的相关化合物的起始材料。将N-苄基四氢-γ-咔啉化合物(III)与叔丁基次氯酸酯卤化，得到一种卤代吲哚啉化合物，该化合物直接与金属二烷基丙二酸盐如铊二烷基丙二酸盐反应，得到一种二烷基3-苄基-1,2,3,4,5,6-六氢-吲哚并(4,5-b)吲哚-5,5-二羧酸酯化合物，后者经过氢化反应得到一种二烷基1,2,3,4,5,6-六氢-吲哚并(4,5-b)吲哚-5,5-二羧酸酯，该化合物与官能化醛，通常是卤代醛缩合，经过中间化合物即二烷基3,3-(烯基)-1,2,3,4,5,6-六氢-吲哚并(4,5-b)吲哚啉-(5,5)-二羧酸盐的盐形式，最终得到文卡地福明或相关衍生物。
• US4267330A
  申请人：——

  公开号：US4267330A

  公开（公告）日：1981-05-12
• US4283536A
  申请人：——

  公开号：US4283536A

  公开（公告）日：1981-08-11
• Studies in biomimetic alkaloid syntheses. 5. Studies syntheses of .psi.-vincadifformine, 20-epi-.psi.-vincadifformine, pandoline, 20-epipandoline, and the C-16 epimeric(carbomethoxy)velbanamines
  作者：Martin E. Kuehne、Curtis L. Kirkemo、Thomas H. Matsko、John C. Bohnert

  DOI：10.1021/jo01304a023

  日期：1980.8