2-vinyladamantane | 81372-28-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 2-vinyladamantane
• 英文别名: 2-ethenyladamantane
• CAS: 81372-28-3
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: OKFAYTDWPOEJQT-UHFFFAOYSA-N

物化性质

• 沸点：
  215.6±7.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-vinyladamantane 在 三氟化硼 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(2-adamantylidene)-3-buten-2-one
  参考文献：
  名称：

  酰基ls盐与不饱和烃的反应

  摘要：

  由β-（乙基硫烷基）丙酰氟和（乙基硫烷基）乙酰氟形成的酰基ulf盐与各种不饱和烃的反应分别通过六元和五元环状sulf盐的形成而进行。用碱成功裂解sulf盐得到相应的含硫不饱和酮。

  DOI：

  10.1016/s0040-4020(01)00897-3
• 作为产物：
  描述：

  2-(2-Trimethylsilanyl-ethyl)-adamantan-2-ol 在 三氟化硼 作用下， 以 溶剂黄146 为溶剂， 生成 2-vinyladamantane
  参考文献：
  名称：

  Cathodic Intra- and Intermolecular Couplings of Ketones with Unsaturated Silanes

  摘要：

  The electroreduction of 6-trimethylsilyl-6-hepten-2-one afforded cis-1-methyl-3-trimethylsilyl cyclohexanol, and gamma-trimethylsilyl alcohols were yielded as the intermolecular coupling products when the cathodic reduction of ketones was carried out in the presence of unsaturated silanes.

  DOI：

  10.1016/00404-0399(50)09172-

文献信息

• Biphilic Organophosphorus Catalysis: Regioselective Reductive Transposition of Allylic Bromides via P^III/P^VRedox Cycling
  作者：Kyle D. Reichl、Nicole L. Dunn、Nicholas J. Fastuca、Alexander T. Radosevich

  DOI：10.1021/jacs.5b01899

  日期：2015.4.29

  We report that a regioselective reductive transposition of primary allylic bromides is catalyzed by a biphilic organophosphorus (phosphetane) catalyst. Spectroscopic, evidence supports the formation of a penta:coordinate (sigma(5)-P) hydridophosphorane as a key reactive intermediate. Kinetics experiments and computational modeling are consistent with a unimolecular docomposition of the sigma(5)-P hydridophosphorane via a conceited cyclic transition,structure that delivers the observed allylic transposition and completes a novel P-III/P-V redox Catalytic cycle. These results broaden the growing repertoire., of reactions catalyzed within the P-III/P-V redox couple and suggest additional opportunities for organophosphorus,catalysis in a biphilic mode.
• [.beta.-(Trimethylsilyl)ethyl]lithium: a new reagent for carbonyl reductive vinylation
  作者：Stephen R. Wilson、Alexander Shedrinsky

  DOI：10.1021/jo00349a038

  日期：1982.5
• Reactions of acylsulfonium salts with unsaturated hydrocarbons
  作者：Valentine G Nenajdenko、Mikhail V Lebedev、Elisabeth S Balenkova

  DOI：10.1016/s0040-4020(01)00897-3

  日期：2001.10

  The reactions of acylsulfonium salts, obtained from β-(ethylsulfanyl)propionyl fluoride and (ethylsulfanyl)acetyl fluoride, with various unsaturated hydrocarbons proceed through the formation of six- and five-membered cyclic sulfonium salts, respectively. Succeeding cleavage of sulfonium salts by bases affords the corresponding sulfur containing unsaturated ketones.

  由β-（乙基硫烷基）丙酰氟和（乙基硫烷基）乙酰氟形成的酰基ulf盐与各种不饱和烃的反应分别通过六元和五元环状sulf盐的形成而进行。用碱成功裂解sulf盐得到相应的含硫不饱和酮。
• Cathodic Intra- and Intermolecular Couplings of Ketones with Unsaturated Silanes
  作者：S Kashimura

  DOI：10.1016/00404-0399(50)09172-

  日期：1995.7.10

  The electroreduction of 6-trimethylsilyl-6-hepten-2-one afforded cis-1-methyl-3-trimethylsilyl cyclohexanol, and gamma-trimethylsilyl alcohols were yielded as the intermolecular coupling products when the cathodic reduction of ketones was carried out in the presence of unsaturated silanes.