ethyl (3aS,6aS)-5,5,6a-trimethyl-4-oxo-3-propan-2-ylidene-2,6-dihydro-1H-pentalene-3a-carboxylate | 1269250-30-7

• 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: ethyl (3aS,6aS)-5,5,6a-trimethyl-4-oxo-3-propan-2-ylidene-2,6-dihydro-1H-pentalene-3a-carboxylate
• CAS: 1269250-30-7
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: AXHLPFWPRIVOEJ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (3aS,6aS)-5,5,6a-trimethyl-4-oxo-3-propan-2-ylidene-2,6-dihydro-1H-pentalene-3a-carboxylate 在 sodium tetrahydroborate 、 magnesium oxide 作用下， 以 甲醇 、 1,1-二氯乙烷 、 乙醇 为溶剂， 反应 11.0h， 生成 (1S,2R,5S)-2-benzyloxy-1-ethoxycarbonyl-3,3,5-trimethyl-8-(propan-2-ylidene)bicyclo[3.3.0]octane
  参考文献：
  名称：

  Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

  摘要：

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.

  DOI：

  10.1021/jo200075v
• 作为产物：
  描述：

  (1S,5S)-1-ethoxycarbonyl-5-methyl-8-(propan-2-ylidene)bicyclo-[3.3.0]octan-2-one 、 碘甲烷 在 水 、 potassium hydride 作用下， 以 乙醚 、 甲苯 、 paraffin oil 为溶剂， 反应 3.0h， 以83%的产率得到ethyl (3aS,6aS)-5,5,6a-trimethyl-4-oxo-3-propan-2-ylidene-2,6-dihydro-1H-pentalene-3a-carboxylate
  参考文献：
  名称：

  Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

  摘要：

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.

  DOI：

  10.1021/jo200075v

文献信息

• Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol
  作者：Douglass F. Taber、Christopher G. Nelson

  DOI：10.1021/jo200075v

  日期：2011.3.18

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.