(R)-4-benzylcyclohex-2-enone | 1394046-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-benzylcyclohex-2-enone
• 英文别名: (4R)-4-benzylcyclohex-2-en-1-one
• CAS: 1394046-15-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: CMBMYOXQJBCPFT-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-Benzyl-5-oxohexanal 在 (S)-2-(pyrrolidinomethyl)pyrrolidine trifluoroacetate 作用下， 以 正己烷 为溶剂， 反应 2.0h， 生成 (R)-4-benzylcyclohex-2-enone 、 (S)-4-benzylcyclohex-2-enone
  参考文献：
  名称：

  Synthesis of Optically Active 4-Substituted 2-Cyclohexenones

  摘要：

  Recently, Nicolaou and Baran independently synthesized optically active 4-substituted 2-cyclohexenones via an efficient LION-mediated intramolecular aldol condensation. Thus far, application of their cyclization approach has been limited to ketoaldehydes where the R-group is branched. It is demonstrated that the LiOH-mediated cyclization, when applied to substrates containing unbranched R-groups, results in significant erosion of optical purity. A mechanistic justification is provided, and a set of neutral, organocatalyzed conditions is identified that enables cyclization with little loss in optical purity.

  DOI：

  10.1021/ol301874x

文献信息

• Catalytic Desymmetrizing Dehydrogenation of 4-Substituted Cyclohexanones through Enamine Oxidation
  作者：Lihui Zhu、Long Zhang、Sanzhong Luo

  DOI：10.1002/anie.201713327

  日期：2018.2.19

  A desymmetrizing dehydrogenation process catalyzed by a chiral primary amine is described herein. The reaction proceeds through the oxidation of a ketone enamine by IBX and enables the highly enantioselective desymmetrization of 4‐substituted cyclohexanones with the generation of chiral 4‐substituted cyclohexenones containing a remote γ‐stereocenter.

  本文描述了由手性伯胺催化的脱对称化脱氢过程。该反应通过IBX对酮烯胺的氧化而进行，并能使4-取代的环己酮高度对映选择性脱对称，并生成含有较远γ-立体中心的手性4-取代的环己酮。
• Synthesis of Optically Active 4-Substituted 2-Cyclohexenones
  作者：Tania I. Houjeiry、Sarah L. Poe、D. Tyler McQuade

  DOI：10.1021/ol301874x

  日期：2012.9.7

  Recently, Nicolaou and Baran independently synthesized optically active 4-substituted 2-cyclohexenones via an efficient LION-mediated intramolecular aldol condensation. Thus far, application of their cyclization approach has been limited to ketoaldehydes where the R-group is branched. It is demonstrated that the LiOH-mediated cyclization, when applied to substrates containing unbranched R-groups, results in significant erosion of optical purity. A mechanistic justification is provided, and a set of neutral, organocatalyzed conditions is identified that enables cyclization with little loss in optical purity.