(1S,2S,9R)-10,12-dioxatricyclo[7.2.1.02,7]dodeca-5,7-dien-4-one | 210155-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2S,9R)-10,12-dioxatricyclo[7.2.1.02,7]dodeca-5,7-dien-4-one
• CAS: 210155-33-2
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: SYEMEEXVTNKXGL-IVZWLZJFSA-N

物化性质

• 沸点：
  372.7±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,9R)-10,12-dioxatricyclo[7.2.1.02,7]dodeca-5,7-dien-4-one 在 camphor-10-sulfonic acid 作用下， 以 吡啶 为溶剂， 反应 1.33h， 生成
  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：

  在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以97%的产率得到(1S,2S,9R)-10,12-dioxatricyclo[7.2.1.02,7]dodeca-5,7-dien-4-one
  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