(R)-4-(4-chlorobenzyl)cyclohex-2-enone | 1394046-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-(4-chlorobenzyl)cyclohex-2-enone
• CAS: 1394046-28-6
• 化学式: C₁₃H₁₃ClO
• 分子量: 220.699
• InChiKey: YWBVUBGBNGLVNP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  在 (S)-2-(pyrrolidinomethyl)pyrrolidine trifluoroacetate 作用下， 以 正己烷 为溶剂， 生成 (R)-4-(4-chlorobenzyl)cyclohex-2-enone 、 (S)-4-(4-chlorobenzyl)cyclohex-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