Z-2-(2¹-butenyl)-1-cyclohexanone | 72128-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-2-(2¹-butenyl)-1-cyclohexanone
• 英文别名: (Z)-2-(2-butenyl)-cyclohexanone；(Z)-2-(but-2-enyl)cyclohexanone；2-(but-2-en-1-yl)cyclohexanone；2-<2-cis-Butenyl>-cyclohexanon；2-[(Z)-but-2-enyl]cyclohexan-1-one
• CAS: 72128-72-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: RNJOUKUODKCLQA-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  ((but-3-en-2-yloxy)methyl)benzene 、 环己酮 在 四氢吡咯 、 1,1'-双(二苯基膦)二茂铁 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 Z-2-(2¹-butenyl)-1-cyclohexanone 、 2-(2-butenyl)cyclohexanone
  参考文献：
  名称：

  Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

  摘要：

  C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

  DOI：

  10.1021/ol5000988

文献信息

• Palladium-Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study
  作者：Xiaohong Huo、Guoqiang Yang、Delong Liu、Yangang Liu、Ilya D. Gridnev、Wanbin Zhang

  DOI：10.1002/anie.201403410

  日期：2014.6.23

  Allylic alcohols were directly used in Pd‐catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co‐catalyst, and a hydrogen‐bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the

  在温和的反应条件下，烯丙醇直接用于钯催化的简单酮的烯丙基烷基化反应。在20°C下，Pd催化剂，吡咯烷助催化剂和氢键合溶剂的协同作用使反应顺利进行，不需要任何其他试剂。一项计算研究表明，甲醇通过降低活化势垒在π-烯丙基铝配合物的形成中起着至关重要的作用。
• Dual Palladium- and Proline-Catalyzed Allylic Alkylation of Enolizable Ketones and Aldehydes with Allylic Alcohols
  作者：Ippei Usui、Stefan Schmidt、Bernhard Breit

  DOI：10.1021/ol9001812

  日期：2009.3.19

  The dual Pd/proline-catalyzed α-allylation reaction of a variety of enolizable ketones and aldehydes with allylic alcohols is described. In this reaction, the choice of a large-bite angle ligand Xantphos and proline as the organocatalyst was essential for generation of the crucial π-allyl Pd intermediate from allylic alcohol, followed by nucleophilic attack of the enamine formed in situ from the corresponding

  描述了多种可烯化的酮和醛与烯丙基醇的双重Pd /脯氨酸催化的α-烯丙基化反应。在该反应中，选择大咬角配体Xantphos和脯氨酸作为有机催化剂对于从烯丙醇生成关键的π-烯丙基Pd中间体至关重要，然后由相应的可烯醇化羰基原位形成烯胺进行亲核攻击底物和脯氨酸。