(S,E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)benzonitrile | 1613507-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S,E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)benzonitrile
• 英文别名: 3-[(E,2S)-4-(4-chlorophenyl)but-3-en-2-yl]benzonitrile
• CAS: 1613507-27-9
• 化学式: C₁₇H₁₄ClN
• 分子量: 267.758
• InChiKey: UMIOEMDZRHJUBJ-GFUIURDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基亚苄基丙酮 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 sodium methylate 、 三乙胺 、 苄基二苯膦 、 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 57.25h， 生成 (S,E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)benzonitrile
  参考文献：
  名称：

  Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines

  摘要：

  We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.

  DOI：

  10.1021/ol5016724

文献信息

• Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines
  作者：Harathi D. Srinivas、Qi Zhou、Mary P. Watson

  DOI：10.1021/ol5016724

  日期：2014.7.3

  We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.