1-(6-Chlorohex-4-enyl)-2-(trimethylsilyl)piperidine | 145388-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(6-Chlorohex-4-enyl)-2-(trimethylsilyl)piperidine
• 英文别名: [1-[(Z)-6-chlorohex-4-enyl]piperidin-2-yl]-trimethylsilane
• CAS: 145388-44-9
• 化学式: C₁₄H₂₈ClNSi
• 分子量: 273.922
• InChiKey: AMFQAPOJGYYBJA-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(6-Chlorohex-4-enyl)-2-(trimethylsilyl)piperidine 在 sodium hydroxide 、 sodium tetrahydroborate 、 二甲基硫 、 萘-1,4-二腈 、 potassium carbonate 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 异丙醇 为溶剂， 反应 8.5h， 生成 1-表羽扇豆碱
  参考文献：
  名称：

  Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

  摘要：

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.

  DOI：

  10.1039/p19960000219
• 作为产物：
  描述：

  2-(三甲基硅烷基)哌啶 在 Lindlar's catalyst 四氯化碳 、 氢气 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、241.32 kPa 条件下， 反应 19.0h， 生成 1-(6-Chlorohex-4-enyl)-2-(trimethylsilyl)piperidine
  参考文献：
  名称：

  Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

  摘要：

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.

  DOI：

  10.1039/p19960000219

文献信息

• Stereoselectivity in the cyclisation of photoinduced electron transfer (PET) generated cyclic (α -amino radicals: First general stereoselective entry to 1-azabicyclo (m:n:o) alkane systems
  作者：Ganesh Pandey、G.Devi Reddy

  DOI：10.1016/s0040-4039(00)79035-6

  日期：1992.10

  Stereoselectivity in the intramolecular cyclisation of PET-generated cyclic alpha-amino radicals and its application to the synthesis of 1-azabicyclo (m:n:o) alkane systems is reported.
• Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine
  作者：Ganesh Pandey、Gottimukkula Devi Reddy、Debasish Chakrabarti

  DOI：10.1039/p19960000219

  日期：——

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.