(1R,5S,2E)-6,6-dimethylcyclo<3.1.1>heptan-2-ylideneacetic acid | 175775-66-3

• 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-dimethylcyclo<3.1.1>heptan-2-ylideneacetic acid
• 英文别名: (2E)-2-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]heptanylidene]acetic acid
• CAS: 175775-66-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OADMSTNZZUFFJZ-NHELSVQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S,2E)-6,6-dimethylcyclo<3.1.1>heptan-2-ylideneacetic acid 在 草酰氯 、 zinc(II) chloride 作用下， 以 乙醚 、 苯 为溶剂， 反应 7.0h， 生成 (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one
  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)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 在 sodium hydroxide 、 (COCl₂)2 、 silver nitrate 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 20.5h， 生成 (1R,5S,2E)-6,6-dimethylcyclo<3.1.1>heptan-2-ylideneacetic acid
  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