11-Oxabicyclo[5.3.1]undec-1(10)-ene | 1192431-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 11-Oxabicyclo[5.3.1]undec-1(10)-ene
• 英文别名: 11-oxabicyclo[5.3.1]undec-1(10)-ene
• CAS: 1192431-37-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: CTYQRUKPKCXHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  11-oxabicyclo[5.3.1]undecan-1-ol 在 对甲苯磺酸 作用下， 90.0~120.0 ℃ 、3.0 kPa 条件下， 生成 11-oxabicyclo[5.3.1]undec-1-ene 、 11-Oxabicyclo[5.3.1]undec-1(10)-ene
  参考文献：
  名称：

  Transformation of Hydroxycycloalkanones to Oxabicycloalkenes

  摘要：

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.

  DOI：

  10.3987/com-09-11728

文献信息

• Transformation of Hydroxycycloalkanones to Oxabicycloalkenes
  作者：Herbert Meier、Guido Krämer、Heiner Detert

  DOI：10.3987/com-09-11728

  日期：——

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.
• Total Synthesis of (−)-Lepistine
  作者：Yusuke Kitabayashi、Satoshi Yokoshima、Tohru Fukuyama

  DOI：10.1021/ol5010033

  日期：2014.6.6

  The first total synthesis of (-)-lepistine has been accomplished in 11 steps from (S)-glycidol. The synthesis features construction of the 10-membered ring via an intramolecular epoxide opening by nosylamide, regioselective dehydration to form an enol ether, and construction of the aminal moiety induced by cleavage of the nosyl groups.