(1S,5R)-6,6-Dimethyl-4-((1E,3E)-4-phenyl-buta-1,3-dienyl)-bicyclo[3.1.1]hept-3-en-2-one | 461669-31-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5R)-6,6-Dimethyl-4-((1E,3E)-4-phenyl-buta-1,3-dienyl)-bicyclo[3.1.1]hept-3-en-2-one
• 英文别名: (1S,5R)-6,6-dimethyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]bicyclo[3.1.1]hept-3-en-2-one
• CAS: 461669-31-8
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: OSLNVJWEOQYLRO-KUGSZZTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,5R)-6,6-Dimethyl-4-((1E,3E)-4-phenyl-buta-1,3-dienyl)-bicyclo[3.1.1]hept-3-en-2-one 在 吡啶 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以48%的产率得到(1R,8S)-9,9-Dimethyl-4-((E)-styryl)-5-selena-tricyclo[6.1.1.0^2,6]deca-2(6),3-dien-7-one
  参考文献：
  名称：

  Novel Reactivity of SeO₂ with 1,3-Dienes:  Selenophene Formation

  摘要：

  A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.

  DOI：

  10.1021/jo025630t
• 作为产物：
  描述：

  马鞭草烯醇 、 肉桂醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以86%的产率得到(1S,5R)-6,6-Dimethyl-4-((1E,3E)-4-phenyl-buta-1,3-dienyl)-bicyclo[3.1.1]hept-3-en-2-one
  参考文献：
  名称：

  Novel Reactivity of SeO₂ with 1,3-Dienes:  Selenophene Formation

  摘要：

  A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.

  DOI：

  10.1021/jo025630t

文献信息

• Novel Reactivity of SeO₂ with 1,3-Dienes:  Selenophene Formation
  作者：Truc M. Nguyen、Ilia A. Guzei、Daesung Lee

  DOI：10.1021/jo025630t

  日期：2002.9.1

  A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.