bicyclo[4.4.0]-5-bromo-5(6)-decen-1-ol | 166111-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bicyclo[4.4.0]-5-bromo-5(6)-decen-1-ol
• 英文别名: 8-bromo-2,3,4,5,6,7-hexahydro-1H-naphthalen-4a-ol
• CAS: 166111-53-1
• 化学式: C₁₀H₁₅BrO
• 分子量: 231.132
• InChiKey: QTDBHHDICVOUMW-UHFFFAOYSA-N

物化性质

• 沸点：
  313.0±25.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bicyclo[4.4.0]-5-bromo-5(6)-decen-1-ol 在 溴 作用下， 生成 trans-6,7-dibromo-11-oxatricyclo[4.3.1.0^1,6]undecane
  参考文献：
  名称：

  13C Scrambling of [5-13C]5-cyclodecynone

  摘要：

  Scrambling of [5-C-13]5-cyclodecynone occurs as a result of acidic conditions that preclude its rapid consumption. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01169-2
• 作为产物：
  描述：

  环癸-5-炔酮 在 氢溴酸 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 bicyclo[4.4.0]-5-bromo-5(6)-decen-1-ol
  参考文献：
  名称：

  The Transannular Rearrangement of 5-Cyclodecynone

  摘要：

  The acid-catalyzed rearrangement of 5-cyclodecynone (1) to bicyclo[4.4.0]-1(6)-decen-2-one (5) has been investigated via C-13 and deuterium labeling experiments, which showed that the transannular rearrangement proceeds by a mechanism not involving an enol of 5-cyclodecynone. Subjecting 5-cyclodecynone to NBS in ethyl ether resulted in the formation of a dibromooxetane 21 which arose from a bromo allylic alcohol 20 formed from 5-cyclodecynone and HBr. The chloro allylic alcohol 28 was formed from HCl and was subsequently converted to enone 5. Pathways were investigated using AM1 calculations. As a result, a modified mechanism consistent with all the experimental data is proposed for the acid-catalyzed rearrangement of 1 to 5.

  DOI：

  10.1021/jo00114a018

文献信息

• Wempe Michael F., Grunwell John R., J. Org. Chem, 60 (1995) N 9, S 2714-2720
  作者：Wempe Michael F., Grunwell John R.

  DOI：——

  日期：——