(3aR,3bR,6aR,7aR)-Decahydro-cyclopenta[a]pentalen-3-one | 144178-62-1

• 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: (3aR,3bR,6aR,7aR)-Decahydro-cyclopenta[a]pentalen-3-one
• 英文别名: (3aR,3bR,6aR,7aR)-1,2,3,3a,3b,5,6,6a,7,7a-decahydrocyclopenta[a]pentalen-4-one
• CAS: 144178-62-1
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: FDSVDXXKTQASSZ-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3aR,3bR,6aR,7aR)-Decahydro-cyclopenta[a]pentalen-3-one 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 cis-transoid-cis-tricyclo[6.3.0.0^2,6]undecane
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036
• 作为产物：
  描述：

  Acetic acid (3aS,3bR,6aR,7aR)-3-oxo-decahydro-cyclopenta[a]pentalen-3a-yl ester 在 盐酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 (3aR,3bR,6aR,7aR)-Decahydro-cyclopenta[a]pentalen-3-one
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036

文献信息

• Intramolecular [2+2] cycloadditions of vinylketenes to olefins. Part II. The synthesis of a linear annelated triquinane derivative.
  作者：Alain De Mesmaeker、Siem J. Veenstra、Beat Ernst

  DOI：10.1016/s0040-4039(00)80121-5

  日期：1988.1

  Regioselective formation of vinylketene , followed by its stereoselective intramolecular [2+2] cycloaddition with an olefin, yielded the linear annelated cis-anti-cis triquinane precursor .

  乙烯酮的区域选择性形成，然后与烯烃进行立体选择性分子内[2 + 2]环加成反应，得到线性退火的顺式-反-顺式三喹烷前体。
• DE, MESMAEKER ALAIN;VEENSTRA, SIEM J.;ERNST, BEAT, TETRAHEDRON LETT., 29,(1988) N 4, 459-462
  作者：DE, MESMAEKER ALAIN、VEENSTRA, SIEM J.、ERNST, BEAT

  DOI：——

  日期：——