(S)-4-phenylcyclohexenone | 1133717-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-phenylcyclohexenone
• 英文别名: (4S)-4-phenylcyclohex-2-en-1-one
• CAS: 1133717-15-3
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: IMZKNYVHHFRIMH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-phenyl-1-trimethylsilyloxy-1-cyclohexene 在 palladium diacetate 、 对苯醌 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-4-phenylcyclohexenone 、 (R)-4-phenylcyclohexenone
  参考文献：
  名称：

  Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

  摘要：

  A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.052

文献信息

• Enantioselective Synthesis of Functionalized Nitrocyclopropanes by Organocatalytic Conjugate Addition of Bromonitroalkanes to α,β-Unsaturated Enones
  作者：Jian Lv、Jiaming Zhang、Zhu Lin、Yongmei Wang

  DOI：10.1002/chem.200801651

  日期：2009.1.12

  A general enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of a variety of bromonitroalkanes to α,β‐unsaturated enone systems is presented. The process, efficiently catalyzed by the salts of 9‐amino‐9‐deoxyepiquinine 1 d serves as a powerful approach to the preparation of synthetically and biologically important cyclopropanes with high levels of

  提出了通过将各种溴硝基烷烃有机共轭加成到α，β-不饱和烯酮体系中来官能化硝基环丙烷的一般对映选择性合成方法。该过程可通过9-氨基-9-脱氧表奎宁1 d的盐有效催化，是制备具有高对映异构和非对映异构选择性的合成和生物学上重要的环丙烷的有力方法。由于仅使用0.6当量的溴硝基甲烷作为试剂，通过使用手性1 d作为其动力学拆分的高效催化剂，对映体纯（S）-2 e（97％  ee在51％转化率下，选择性s = 120） 。