5,5-dimethyl-3-(1-methylpropyl)cyclohex-2-en-1-one | 93136-18-6

• 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: 5,5-dimethyl-3-(1-methylpropyl)cyclohex-2-en-1-one
• 英文别名: 3-sec-butyl-5,5-dimethylcyclohex-2-enone；3-Butan-2-yl-5,5-dimethylcyclohex-2-en-1-one
• CAS: 93136-18-6
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: CTBHQQXCBXSQPT-UHFFFAOYSA-N

物化性质

• 沸点：
  250.4±10.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  5,5-dimethyl-3-(1-methylpropyl)cyclohex-2-en-1-one 、 三甲基氯硅烷 、 三乙胺 、 甲基溴化镁 生成 (5-butan-2-yl-3,3-dimethylcyclohexa-1,5-dien-1-yl)oxy-trimethylsilane
  参考文献：
  名称：

  KRAFFT, M. E.;HOLTON, R. A., J. AMER. CHEM. SOC., 1984, 106, N 24, 7619-7621

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 5,5-dimethyl-3-oxocyclohex-1-enyl phosphate 在 碲化氢 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.66h， 生成 5,5-dimethyl-3-(1-methylpropyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Diastereoselective synthesis of α,β-unsaturated systems

  摘要：

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.025

文献信息

• Iron Thiolate Complexes: Efficient Catalysts for Coupling Alkenyl Halides with Alkyl Grignard Reagents
  作者：Gérard Cahiez、Olivier Gager、Julien Buendia、Cindy Patinote

  DOI：10.1002/chem.201200184

  日期：2012.5.7

  Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron‐catalyzed cross‐coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo‐ and stereoselective. With this new procedure, the use of N‐methylpyrrolidone as a co‐solvent is no longer required.

  解决问题：描述了基于硫醇铁的高效新型催化体系，用于烷基格氏试剂与链烯基卤化物的铁催化交叉偶联（参见方案）。该反应是高度化学和立体选择性的。通过此新程序，不再需要使用N-甲基吡咯烷酮作为助溶剂。
• The Kharasch reagent. Regioselective generation of dienyl ethers from enones
  作者：Marie E. Krafft、Robert A. Holton

  DOI：10.1021/ja00336a051

  日期：1984.11
• Diastereoselective synthesis of α,β-unsaturated systems
  作者：Priscila Castelani、João V. Comasseto

  DOI：10.1016/j.tet.2005.01.025

  日期：2005.2

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.
• KRAFFT, M. E.;HOLTON, R. A., J. AMER. CHEM. SOC., 1984, 106, N 24, 7619-7621
  作者：KRAFFT, M. E.、HOLTON, R. A.

  DOI：——

  日期：——