8,8-dimethyl-bicyclo<3.3.0>oct-1(5)-en-2-one | 81332-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,8-dimethyl-bicyclo<3.3.0>oct-1(5)-en-2-one
• 英文别名: 8,8-dimethylbicyclo<3.3.0>oct-1(5)-en-2-one；6,6-dimethyl-3,4,5,6-tetrahydro-1(2H)-pentalenone；6,6-dimethyl-2,3,4,5-tetrahydropentalen-1-one
• CAS: 81332-19-6
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: XLOSJJHYKQYOFF-UHFFFAOYSA-N

物化性质

• 沸点：
  241.4±7.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  8,8-dimethyl-bicyclo<3.3.0>oct-1(5)-en-2-one 以 乙醚 为溶剂， 生成 2-ethynyl-5,8,8-trimethyl-bicyclo<3.3.0>octan-2-ol
  参考文献：
  名称：

  立体控制的（± ） -Δ9 （12） -capnellene的全合成

  摘要：

  描述了海洋三喹烷倍半萜烯Δ9 （12） -capnellene（1）的第一个全合成。

  DOI：

  10.1016/s0040-4039(01)82965-8
• 作为产物：
  描述：

  3-(3,3-Dimethyl-2-oxocyclopentyl)propanenitrile 在 甲酸 、 硫酸 、 四乙基对甲苯磺酸铵 作用下， 以 异丙醇 为溶剂， 反应 2.25h， 生成 8,8-dimethyl-bicyclo<3.3.0>oct-1(5)-en-2-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

• Stereocontrolled total synthesis of (±)-Δ9(12)-capnellene
  作者：Kenneth E. Stevens、Leo A. Paquette

  DOI：10.1016/s0040-4039(01)82965-8

  日期：1981.1

  The first total synthesis of the marine triquinane sesquiterpene Δ9(12)-capnellene (1) is described.

  描述了海洋三喹烷倍半萜烯Δ9 （12） -capnellene（1）的第一个全合成。
• Rearrangements initiated by trimethylsilyl iodide: ready deoxygenative rearrangement of bicyclo[4.2.0]octane-2,5-diones to bicyclo[3.3.0]oct-1(5)-en-2-ones
  作者：Kaoru Sasaki、Takahiro Kushida、Masahiko Iyoda、Masaji Oda

  DOI：10.1016/s0040-4039(00)87276-7

  日期：1982.1

  Reaction of bicyclo[4.2.0]octane-2,5-diones with trimethylsilyl iodide gave bicyclo[3.3.0]oct-1(5)-en-2-ones by a clean reductive rearrangement in good yields, providing a simple and effecient synthetic method for the enones.

  双环[4.2.0]辛烷-2,5-二酮与碘化三甲基甲硅烷基的反应通过干净的还原重排以良好的收率得到双环[3.3.0] oct-1（5）-en-2-one，提供了简单而又烯酮的有效合成方法。
• A short and efficient synthesis of capnellene
  作者：Masahiko Iyoda、Takahiro Kushida、Sumiko Kitami、Masaji Oda

  DOI：10.1039/c39870001607

  日期：——

  A short synthesis of the marine triquinane sesquiterpene capnell-9(12)-ene based on titanium-induced oxo ester cyclization as the key step for construction of the cis-transoid-cis-tricyclo[6.3.0.02,6]undecane skeleton is described.

  海洋的短合成倍半萜烯triquinane capnell-9（12） -烯基于钛诱导的氧代酯环化作为用于构建的关键步骤顺- transoid -顺式-三环[6.3.0.0 2,6 ]十一烷骨架是描述。
• Synthesis of cyclic organic compounds
  申请人：Univation Technologies, LLC

  公开号：US10975012B2

  公开（公告）日：2021-04-13

  A method comprising synthesizing a cyclic organic compound (3) via reaction of an substituted alkene (1) with an unsubstituted or substituted acrylic acid (2) in the presence of a sulfonic acid reagent to make the cyclic organic compound (3) R1(H)C═C(H)R2 (1)

  一种方法，包括在磺酸试剂存在下，通过取代的烯烃（1）与未取代或取代的丙烯酸（2）反应合成环状有机化合物（3），从而制得环状有机化合物（3） R1(H)C═C(H)R2 (1)
• SASAKI, KAORU;KUSHIDA, TAKAHIRO;IYODA, MASAHIKO;ODA, MASAJI, TETRAHEDRON LETT., 1982, 23, N 20, 2117-2120
  作者：SASAKI, KAORU、KUSHIDA, TAKAHIRO、IYODA, MASAHIKO、ODA, MASAJI

  DOI：——

  日期：——