5-Methyl-1-azabicyclo<4.4.0>decane | 491-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 5-Methyl-1-azabicyclo<4.4.0>decane
• 英文别名: (+/-)-epilupinane；(+/-)-Epilupinan；(+/-)-1c-Methyl-(2arH)-octahydro-2H-chinolizin；(1S,9aR)-1-methyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine
• CAS: 491-43-0；4772-55-8；5581-88-4；5581-89-5；18396-98-0；31085-23-1；31097-79-7；145416-69-9
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: VZEGBIWAIFLVJH-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 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

• 作为反应物：
  描述：

  5-Methyl-1-azabicyclo<4.4.0>decane 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以95%的产率得到(1S,9aR)-1-(chloromethyl)octahydro-2H-quinolizine
  参考文献：
  名称：

  Boido; Sparatore, Farmaco, Edizione Scientifica, 1982, vol. 37, # 1, p. 63 - 73

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Boc-哌啶 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<4.4.0>decane
  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

• PROTEIN KINASE C INHIBITORS AND USES THEREOF
  申请人：RIGEL PHARMACEUTICALS, INC.

  公开号：US20140163022A1

  公开（公告）日：2014-06-12

  This disclosure concerns compounds which are useful as inhibitors of protein kinase C (PKC) and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC. This disclosure also relates to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本公开涉及的化合物可用作蛋白激酶C（PKC）的抑制剂，因此可用于治疗通过PKC活性介导或维持的各种疾病和障碍。本公开还涉及包括这些化合物的药物组合物，使用这些化合物治疗各种疾病和障碍的方法，制备这些化合物的过程以及这些过程中有用的中间体。
• 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.
• Clemo; Raper, Chemische Berichte, 1934, vol. 67, p. 463
  作者：Clemo、Raper

  DOI：——

  日期：——
• Unsaturated Amines. II. Determination of the Proximity of Nitrogen to a Double Bond by Ultraviolet Absorption Spectra¹
  作者：Nelson J. Leonard、David M. Locke

  DOI：10.1021/ja01607a064

  日期：1955.1
• Winterfeld et al., Chemische Berichte, 1931, vol. 64, p. 2415,2418
  作者：Winterfeld et al.

  DOI：——

  日期：——