5-Methyl-1-azabicyclo<4.3.0>nonane | 90949-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: 5-Methyl-1-azabicyclo<4.3.0>nonane
• 英文别名: (8S,8aR)-8-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• CAS: 90949-01-2；145388-42-7；145388-48-3
• 化学式: C₉H₁₇N
• 分子量: 139.241
• InChiKey: IUMLDTRLJSLIFQ-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-Boc-四氢吡咯 在 四甲基乙二胺 、 萘-1,4-二腈 、 仲丁基锂 、 potassium carbonate 、 三氟乙酸 作用下， 以 异丙醇 为溶剂， 反应 8.5h， 生成 5-Methyl-1-azabicyclo<4.3.0>nonane
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)79035-6

文献信息

• Titanium-Mediated Cyclization of ω-Vinyl Imides in Alkaloid Synthesis:  Isoretronecanol, Trachelanthamidine, 5-Epitashiromine, and Tashiromine
  作者：Se-Ho Kim、Seok-In Kim、Sheng Lai、Jin Kun Cha

  DOI：10.1021/jo9907383

  日期：1999.9.1

  A new method for the stereocontrolled synthesis of pyrrolizidine and indolizidine alkaloids by means of titanium-mediated cyclization of omega-vinyl imides is described. The general procedure involves treatment of readily available omega-vinyl imides 9 and 10 with 2.5 equiv of cyclopentylmagnesium chloride in the presence of ClTi(O-i-Pr)(3) (1.1 equiv) and subsequent stereoselective reduction of the

  描述了一种新的方法，该方法通过钛介导的ω-乙烯基酰亚胺的环化立体控制合成吡咯烷和吲哚并立生物碱。一般程序包括在ClTi（Oi-Pr）（3）（1.1当量）存在下用2.5当量的环戊基氯化镁处理容易获得的欧米茄乙烯基酰亚胺9和10，随后立体选择性还原N-酰基组。顺式和反式环结立体异构体可以分别通过催化氢化（H（2），PtO（2），EtOAc）和NaCNBH（3）还原（TFA，MeOH）进行立体选择性制备。最后，用LAH或乙硼烷处理所得内酰胺以良好的收率得到目标生物碱1-8。
• Chiral organolithium species: determination of the rate of cyclization and extent of racemization
  作者：Iain Coldham、Graham P. Vennall

  DOI：10.1039/b004519p

  日期：——

  The rate of intramolecular carbolithiation onto an unactivated alkene to give a six-membered ring has been determined and follows first order kinetics with a half life of ∼90 min at 23 °C; this allows significant racemization using a chiral organolithium species, although good levels of optical purity are obtained with a phenylthio-substituted alkene.

  分子内烃基化到未活化的非官能性烯烃上形成六元环的速率已经确定，遵循一阶动力学，在23°C时半衰期为90分钟；这允许使用手性有机锂物种进行显著的消旋化，尽管使用苯硫基取代的烯烃可以获得很好的光学纯度。
• 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.