(2R,3S,8S)-8-ethoxycarbonyl-2-hydroxymethyl-5,6-dimethyl-9-oxo-1-aza-bicyclo[4.3.0]non-5-ene | 166765-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2R,3S,8S)-8-ethoxycarbonyl-2-hydroxymethyl-5,6-dimethyl-9-oxo-1-aza-bicyclo[4.3.0]non-5-ene
• CAS: 166765-43-1
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: LVOFXPDQSNYWSZ-GYSYKLTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (2R,3S,8S)-8-ethoxycarbonyl-2-hydroxymethyl-5,6-dimethyl-9-oxo-1-aza-bicyclo[4.3.0]non-5-ene 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以83%的产率得到(1S,3aS,7aS)-5,6-Dimethyl-3-oxo-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester
  参考文献：
  名称：

  Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions

  摘要：

  The alpha,beta-unsaturated bicyclic lactams 3a,c, prepared from (S)-pyroglutamic acid, are useful substrates for cycloaddition reactions, giving excellent regio-and diastereocontrol; however, lactam 3c has very superior reactivity with several dienes and dipoles under mild reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00740-0
• 作为产物：
  描述：

  (2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 76.0h， 生成 (2R,3S,8S)-8-ethoxycarbonyl-2-hydroxymethyl-5,6-dimethyl-9-oxo-1-aza-bicyclo[4.3.0]non-5-ene
  参考文献：
  名称：

  Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions

  摘要：

  The alpha,beta-unsaturated bicyclic lactams 3a,c, prepared from (S)-pyroglutamic acid, are useful substrates for cycloaddition reactions, giving excellent regio-and diastereocontrol; however, lactam 3c has very superior reactivity with several dienes and dipoles under mild reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00740-0

文献信息

• A concise approach to functionalised, homochiral pyrrolidinones
  作者：Mark J Bamford、Mark Beard、David T Cherry、Mark G Moloney

  DOI：10.1016/0957-4166(95)00007-c

  日期：1995.2

  Acylation of O,N-acetal 1 gives excellent yields of the C-7 substituted products 2a,b. Alkylation of 2a under mild conditions gives high yields of the exo- 3 and endo- 4 substituted products in varying ratios, depending on the alkylating agent. The unsaturated derivative 8 reacts in high yields under mild conditions with dienes and 1,3-dipoles to give the corresponding cycloadducts. Elaboration of these compounds by acidic deprotection to substituted pyroglutaminols, and oxidation to the corresponding pyroglutamates, can be readily achieved.