(S,E)-4-phenyl-dodec-5-en-2-one

• 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: (S,E)-4-phenyl-dodec-5-en-2-one
• 英文别名: (E,4S)-4-phenyldodec-5-en-2-one
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: LBBJULJDTOOZOA-MOVXZBDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  dimethyl (1E)-1-octenylboronate 、 苄叉丙酮 在 (R)-3,3'-bisiodo-1,1'-binaphthalen-2,2'-diol 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以81%的产率得到(S,E)-4-phenyl-dodec-5-en-2-one
  参考文献：
  名称：

  Asymmetric Conjugate Alkenylation of Enones Catalyzed by Chiral Diols

  摘要：

  Reaction of dimethyl alkenylboronates with alpha,beta-unsaturated ketones in the presence of catalytic amounts of 3,3'-disubstituted binaphthols provides conjugate alkenylation products in good yields and with generally high (similar to 99:1 er) stereoselectivities.

  DOI：

  10.1021/ja0713734

文献信息

• Asymmetric 1,4-addition of alkenylzirconium reagents to α,β-unsaturated ketones catalyzed by chiral rhodium complexes
  作者：Shuichi Oi、Takashi Sato、Yoshio Inoue

  DOI：10.1016/j.tetlet.2004.04.171

  日期：2004.6

  Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to alpha-enones Was found to be catalyzed by a chiral rhodium complex generated from [Rh(cod)(MeCN)(2)]BF4 and (S)-BINAP. The reaction can be applied to either cyclic or acyclic enones and the optical yield was LIP to 99% ee. The reaction mechanism would involve the transmetalation between the alkenylzirconocene chloride and the rhodium complex to give the alkenylrhodium species as a key intermediate. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric Conjugate Alkenylation of Enones Catalyzed by Chiral Diols
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ja0713734

  日期：2007.4.1

  Reaction of dimethyl alkenylboronates with alpha,beta-unsaturated ketones in the presence of catalytic amounts of 3,3'-disubstituted binaphthols provides conjugate alkenylation products in good yields and with generally high (similar to 99:1 er) stereoselectivities.