1-methanesulfonyloxy-4-dimethoxymethyl-hexane | 66859-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-methanesulfonyloxy-4-dimethoxymethyl-hexane
• 英文别名: 1-Methansulfonyl-4-(dimethoxymethyl)hexan；4-Dimethoxymethyl-1-methanesulfonyloxyhexane；4-(dimethoxymethyl)hexyl methanesulfonate
• CAS: 66859-28-7
• 化学式: C₁₀H₂₂O₅S
• 分子量: 254.348
• InChiKey: RDWVZWGMYICXMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methanesulfonyloxy-4-dimethoxymethyl-hexane 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-2-ethyl-1-pentanal
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 2. Synthesis of vincadifformine from tetrahydro-.beta.-carboline through a secodine intermediate

  摘要：

  DOI：

  10.1021/jo00413a015
• 作为产物：
  描述：

  4-二甲氧基甲基己酸甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 1-methanesulfonyloxy-4-dimethoxymethyl-hexane
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 2. Synthesis of vincadifformine from tetrahydro-.beta.-carboline through a secodine intermediate

  摘要：

  DOI：

  10.1021/jo00413a015

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，这些衍生物可用作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-咔唑啉（II）与苯甲酰氯反应，得到2-苯甲酰基-1,2,3,4-四氢-9H-吡啶并（3,4-b）吲哚（III）。然后将化合物（III）还原得到2-苄基-1,2,3,4-四氢-9H-吡啶并（3,4-b）吲哚（IV）。然后，化合物（IV）通过叔丁基次氯酸酯转化为氯吲哚啉衍生物（V），立即用金属二烷基丙二酸盐（如丁基甲基丙二酸铊）处理，得到二烷基-3-苄基-1,2,3,4,5,6-六氢-吖啶并（4,5-b）吲哚-5,5-二羧酸酯（VI）。然后，将化合物（VI）部分脱羧成烷基-3-苄基-1,2,3,4,5,6-六氢-（4,5-b）吲哚-5-羧酸酯（VII）。将化合物（VII）加氢得到烷基-1,2,3,4,5,6-六氢-吖啶并（4,5-b）吲哚-5-羧酸酯（VIII）。在另一种实施方案中，化合物（VI）可加氢至相应的二烷基-1,2,3,4,5,6-六氢-吖啶并（4,5-b）吲哚-5,5-二羧酸酯，然后脱羧成化合物（VIII）。将化合物（VIII）与官能化醛（通常是环氧醛或卤代醛，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。
• Studies in biomimetic alkaloid syntheses. 4. An alternative route to secodine intermediates providing syntheses of minovine, vincadifformine, ervinceine, and N(a)-methylervinceine
  作者：Martin E. Kuehne、James A. Huebner、Thomas H. Matsko

  DOI：10.1021/jo01328a030

  日期：1979.7
• US4283536A
  申请人：——

  公开号：US4283536A

  公开（公告）日：1981-08-11
• Studies in biomimetic alkaloid syntheses. 2. Synthesis of vincadifformine from tetrahydro-.beta.-carboline through a secodine intermediate
  作者：Martin E. Kuehne、Dennis M. Roland、Russell Hafter

  DOI：10.1021/jo00413a015

  日期：1978.9