(1R,5S,2E)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetyl chloride | 175611-77-5

• 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: (1R,5S,2E)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetyl chloride
• CAS: 175611-77-5
• 化学式: C₁₁H₁₅ClO
• 分子量: 198.692
• InChiKey: QVGKOYJLZIWQBB-NHELSVQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1R,5S,2E)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetyl chloride 在 palladium on activated charcoal 硫酸 、 氢气 、 四氯化钛 、 zinc(II) chloride 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸
  参考文献：
  名称：

  The Synthesis of (-)-Robustadial A and Some Analogues.

  摘要：

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.

  DOI：

  10.3891/acta.chem.scand.50-0132
• 作为产物：
  描述：

  (1R,5S,2E)-6,6-dimethylcyclo<3.1.1>heptan-2-ylideneacetic acid 在 草酰氯 作用下， 以 苯 为溶剂， 反应 5.0h， 以84%的产率得到(1R,5S,2E)-6,6-dimethylbicyclo<3.1.1>heptan-2-ylideneacetyl chloride
  参考文献：
  名称：

  The Synthesis of (-)-Robustadial A and Some Analogues.

  摘要：

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.

  DOI：

  10.3891/acta.chem.scand.50-0132