(1S,2S,8S,9R)-6-Bromo-4-trimethylsilanylmethyl-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-8-ol | 210155-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,2S,8S,9R)-6-Bromo-4-trimethylsilanylmethyl-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-8-ol
• CAS: 210155-28-5
• 化学式: C₁₄H₂₁BrO₃Si
• 分子量: 345.308
• InChiKey: XVFNTTGDBOMPHR-QIRAZROLSA-N

反应信息

• 作为反应物：
  描述：

  (1S,2S,8S,9R)-6-Bromo-4-trimethylsilanylmethyl-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-8-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.17h， 生成 (1S,2S,9R)-6-Bromo-4-methylene-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-5,7-diene
  参考文献：
  名称：

  Stereoelectronic and steric control in chiral cyclohexane synthesis toward (−)-tetrodotoxin

  摘要：

  The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an a-hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00331-7
• 作为产物：
  描述：

  (1S,2S,8S,9R)-6-Tributylstannanyl-4-trimethylsilanylmethyl-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-8-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 (1S,2S,8S,9R)-6-Bromo-4-trimethylsilanylmethyl-10,12-dioxa-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-8-ol
  参考文献：
  名称：

  Stereoelectronic and steric control in chiral cyclohexane synthesis toward (−)-tetrodotoxin

  摘要：

  The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an a-hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00331-7