(3aR*,5'R*,9aS*)-7-chloro-2,3'-trimethyl-2,3,3a,9a-tetrahydro-1H-spiro[chromeno[2,3-c]pyrrole-9,5'-oxazolidine]-9a-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3aR*,5'R*,9aS*)-7-chloro-2,3'-trimethyl-2,3,3a,9a-tetrahydro-1H-spiro[chromeno[2,3-c]pyrrole-9,5'-oxazolidine]-9a-carbonitrile
• 英文别名: (3'aR,5R,9'aS)-7'-chloro-2',3-dimethylspiro[1,3-oxazolidine-5,9'-3,3a-dihydro-1H-chromeno[2,3-c]pyrrole]-9'a-carbonitrile
• 化学式: C₁₆H₁₈ClN₃O₂
• 分子量: 319.791
• InChiKey: OAHHJBMXGSVPAV-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR*,5'R*,9aS*)-7-chloro-2,3'-trimethyl-2,3,3a,9a-tetrahydro-1H-spiro[chromeno[2,3-c]pyrrole-9,5'-oxazolidine]-9a-carbonitrile 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 以63%的产率得到(3aS*,6aR*,11bR*)-10-chloro-3-imino-2,5-dimethyl-1,2,3,4,5,6,6a,11b-octahydrochromeno[2,3-c:3,4-c']dipyrrol-11b-ol
  参考文献：
  名称：

  Substituted chromones in [3+2] cycloadditions with nonstabilized azomethine ylides: synthesis of 1-benzopyrano[2,3-c]pyrrolidines and 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines

  摘要：

  Chromones bearing electron-withdrawing substituents at the 2- or 3-position react with nonstabilized azomethine ylides to produce 1-benzopyrano[2,3-c]pyrrolidines in good yields. Reactions of 3cyanochromones proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3-c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.090
• 作为产物：
  描述：

  6-氯色酮-3-腈 、 聚合甲醛 、 肌氨酸 以 苯 为溶剂， 反应 4.0h， 以32%的产率得到(3aR*,5'R*,9aS*)-7-chloro-2,3'-trimethyl-2,3,3a,9a-tetrahydro-1H-spiro[chromeno[2,3-c]pyrrole-9,5'-oxazolidine]-9a-carbonitrile
  参考文献：
  名称：

  Substituted chromones in [3+2] cycloadditions with nonstabilized azomethine ylides: synthesis of 1-benzopyrano[2,3-c]pyrrolidines and 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines

  摘要：

  Chromones bearing electron-withdrawing substituents at the 2- or 3-position react with nonstabilized azomethine ylides to produce 1-benzopyrano[2,3-c]pyrrolidines in good yields. Reactions of 3cyanochromones proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3-c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.090

文献信息

• 3-Cyanochromones in [3+2] cycloadditions with an azomethine ylide derived from sarcosine and formaldehyde. A short synthesis of 1-benzopyrano[2,3-c:3,4-c′]dipyrrolidines
  作者：Vyacheslav Ya. Sosnovskikh、Mikhail Yu. Kornev、Vladimir S. Moshkin

  DOI：10.1016/j.tetlet.2013.10.154

  日期：2014.1

  Reactions of 3-cyanochromones with sarcosine and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[2,3-c]pyrrolidines and tetrahydro-1H-spiro[chromeno[2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbonitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno[2,3c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2013 Elsevier Ltd. All rights reserved.