1-acetyl-1-allylcyclohexane | 29517-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetyl-1-allylcyclohexane
• 英文别名: 1-(1-Prop-2-enylcyclohexyl)ethanone
• CAS: 29517-73-5
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: WMOVALVNIHFMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1-acetyl-1-allylcyclohexane 在 盐酸 、 双(乙腈)氯化钯(II) 、 copper dichloride 作用下， 以 1,4-二氧六环 为溶剂， 以55%的产率得到2,2-五亚甲基环己酮
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Hydroalkylation of Unactivated Olefins with Dialkyl Ketones

  摘要：

  Treatment of 3-butenyl heptyl ketone with substoichiometric amounts of PdCl2(CH3CN)(2) (10 mol %), HCl (0.1 equiv), and CuCl2 (0.3 equiv) in dioxane at 70 degreesC for 12 h in a sealed tube formed 2-hexylcyclohexanone in 77% isolated yield. A number of alkyl 3-butenyl ketones underwent hydroalkylation under these conditions to form 2-substituted cyclohexanones in moderate to good yield.

  DOI：

  10.1021/ol034879+
• 作为产物：
  描述：

  1-allylcyclohexanecarbaldehyde 、 甲基锂 生成 1-acetyl-1-allylcyclohexane
  参考文献：
  名称：

  Introduction of two carbon appendages at a carbonyl carbon. Application to double chain branching and spiro annulation operations

  摘要：

  DOI：

  10.1021/ja00721a042

文献信息

• Palladium-Catalyzed Intramolecular Hydroalkylation of Alkenyl- ?-Keto Esters, ?-Aryl Ketones, and Alkyl Ketones in the Presence of Me3SiCl or HCl
  作者：Xiaoqing Han、Xiang Wang、Tao Pei、Ross A. Widenhoefer

  DOI：10.1002/chem.200400459

  日期：2004.12.17

  palladium-catalyzed hydroalkylation, but rather served as a source of HCl, which presumably catalyzes enolization of the ketone. Identification of HCl as the active promoter of palladium-catalyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2, HCl, and CuCl2 in a sealed tube at 70 degrees C.

  3-丁烯基β-酮酸酯或3-丁烯基α-芳基酮与催化量的[PdCl2（CH3CN）2]（2）和化学计量的Me3SiCl或Me3SiCl / CuCl2在二恶烷中的反应温度为25-70摄氏度以高产率和高区域选择性生成2-取代的环己酮。该方案容许许多酯和芳基，并容许在烯丙基，烯醇，顺式和反式末端烯烃位置上的取代。原位NMR实验表明，氯硅烷并不直接参与钯催化的加氢烷基化反应，而是用作HCl的来源，推测是催化酮的烯醇化反应。
• Palladium-Catalyzed Intramolecular Hydroalkylation of Unactivated Olefins with Dialkyl Ketones
  作者：Xiang Wang、Tao Pei、Xiaoqing Han、Ross A. Widenhoefer

  DOI：10.1021/ol034879+

  日期：2003.7.1

  Treatment of 3-butenyl heptyl ketone with substoichiometric amounts of PdCl2(CH3CN)(2) (10 mol %), HCl (0.1 equiv), and CuCl2 (0.3 equiv) in dioxane at 70 degreesC for 12 h in a sealed tube formed 2-hexylcyclohexanone in 77% isolated yield. A number of alkyl 3-butenyl ketones underwent hydroalkylation under these conditions to form 2-substituted cyclohexanones in moderate to good yield.
• Introduction of two carbon appendages at a carbonyl carbon. Application to double chain branching and spiro annulation operations
  作者：Elias J. Corey、Joel I. Shulman

  DOI：10.1021/ja00721a042

  日期：1970.9