(3aR,8aS)-6,7-Dihydro-3aH-furo[2,3-d]thieno[3,2-c]isoxazole | 135082-41-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (3aR,8aS)-6,7-Dihydro-3aH-furo[2,3-d]thieno[3,2-c]isoxazole
• 英文别名: (1S,5R)-2,6-dioxa-11-thia-7-azatricyclo[6.3.0.01,5]undeca-3,7-diene
• CAS: 135082-41-6
• 化学式: C₇H₇NO₂S
• 分子量: 169.204
• InChiKey: LFCYXVKVCRFRCR-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,8aS)-6,7-Dihydro-3aH-furo[2,3-d]thieno[3,2-c]isoxazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(1S,5R)-2,6-dioxa-11λ4-thia-7-azatricyclo[6.3.0.01,5]undeca-3,7-diene 11-oxide
  参考文献：
  名称：

  分子内一氧化氮环化成呋喃的区域和立体选择性

  摘要：

  分子内一氧化氮环加成到官能化呋喃中的过程是完全的区域化学控制，但非对映选择性低。

  DOI：

  10.1016/s0040-4039(01)80569-4
• 作为产物：
  描述：

  2-(3-Iodo-propylsulfanyl)-furan 在 对氯苯异氰酸酯 、 三乙胺 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 (3aR,8aS)-6,7-Dihydro-3aH-furo[2,3-d]thieno[3,2-c]isoxazole
  参考文献：
  名称：

  Regio- and stereocontrol in the intramolecular nitrile oxide cycloaddition to 2-furylthiol- and 2-furylmethanethiol derivatives.

  摘要：

  A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chain length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yield. Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction. Enantiomerically enriched products (e.e. less-than-or-equal-to 95%) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.

  DOI：

  10.1016/s0040-4020(01)80910-8

文献信息

• Regio- and stereoselectivity of intramolecular nitrile oxide cycloaddition to furan
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4039(01)80569-4

  日期：1989.1

  Intramolecular nitrile oxide cycloaddition to functionalized furans occurs with complete regiochemical control but low diastereoselectivity.

  分子内一氧化氮环加成到官能化呋喃中的过程是完全的区域化学控制，但非对映选择性低。
• Regio- and stereocontrol in the intramolecular nitrile oxide cycloaddition to 2-furylthiol- and 2-furylmethanethiol derivatives.
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Laura Raimondi、Giulia Licini

  DOI：10.1016/s0040-4020(01)80910-8

  日期：——

  A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chain length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yield. Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction. Enantiomerically enriched products (e.e. less-than-or-equal-to 95%) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.