(1S,5R,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>oct-3-en-7-one | 119184-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (1S,5R,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>oct-3-en-7-one
• 英文别名: (1S,5R,8R)-8-hydroxy-6-isopropyl-6-azabicyclo[3.2.1]oct-3-en-7-one；(1S,5R,8S)-8-hydroxy-6-propan-2-yl-6-azabicyclo[3.2.1]oct-3-en-7-one
• CAS: 119184-50-8
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MIEVQVJWKFPRQH-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5R,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>oct-3-en-7-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以96%的产率得到(1S*,5R*)-6-isopropyl-6-aza-bicyclo[3.2.1]oct-3-en-7,8-dione
  参考文献：
  名称：

  Synthesis and absolute configuration of the Aristotelia alkaloid peduncularine

  摘要：

  DOI：

  10.1021/ja00189a036
• 作为产物：
  描述：

  (S)-acetoxy-1-isopropylsuccinimide 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 甲酸 、 硫酸 、 氨 、 sodium ethanolate 、 臭氧 、 lithium diisopropyl amide 作用下， 以 吡啶 、 乙醇 为溶剂， -20.0~600.0 ℃ 、6.67 Pa 条件下， 反应 108.5h， 生成 (1S,5R,8S)-8-hydroxy-6-isopropyl-6-azabicyclo<3.2.1>oct-3-en-7-one
  参考文献：
  名称：

  Synthesis and absolute configuration of the Aristotelia alkaloid peduncularine

  摘要：

  DOI：

  10.1021/ja00189a036

文献信息

• Concise Formal Synthesis of (−)-Peduncularine via Ring-Closing Metathesis
  作者：David G. Washburn、Richard W. Heidebrecht、Stephen F. Martin

  DOI：10.1021/ol0354066

  日期：2003.9.1

  [reaction: see text] A synthesis of the 6-aza[3.2.1]bicyclooctene (-)-2 has been completed by a short sequence of reactions that required only six operations from (S)-malic acid and featured a novel ring-closing metathesis to form the bridged bicyclic ring. Because 2 was previously converted into (-)-peduncularine (1), its preparation constitutes a formal enantioselective synthesis of 1.

  [反应：请参阅文本]通过短序列的反应即可完成6-氮杂[3.2.1]双环辛烯（-）-2的合成，该反应仅需从（S）-苹果酸进行六次操作，并具有一个新的环闭复分解反应形成桥连的双环。由于2先前已被转换为（-）-peduncularine（1），因此其制备构成了1的形式对映选择性合成。
• Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals
  作者：Xichen Lin、Gerald D. Artman、Didier Stien、Steven M. Weinreb

  DOI：10.1016/s0040-4020(01)00878-x

  日期：2001.10

  New methodology has been devised for the generation and subsequent cyclization of iminyl and amidyl radicals under mild conditions. The process involves either the treatment of oximes with 2,6-dimethylbenzenesulfinyl chloride, or the treatment of hydroxamic acids with tert-butylsulfinyl chloride (-50 degreesC to rt), to give the corresponding nitrogen radicals, followed by cyclization onto pendant olefins. Radical traps such as diphenyl diselenide, diphenyl disulfide, and TEMPO can be used to terminate the cyclizations, thus introducing functionality that provides multiple options for further manipulation. In a more convenient procedure, both iminyl and amidyl radical cyclizations can be initiated using commercially available diethyl chlorophosphite which generally provides similar (with diphenyl disulfide and TEMPO) or significantly higher (with diphenyl diselenide) yields of products. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and absolute configuration of the Aristotelia alkaloid peduncularine
  作者：Wim J. Klaver、Hiemstra Henk、W. Nico Speckamp

  DOI：10.1021/ja00189a036

  日期：1989.3