(Z)-1-(p-acetamidophenyl)-3,3-dimethyl-1-(4-phenylcyclohex-1-enyl)-1-butene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-1-(p-acetamidophenyl)-3,3-dimethyl-1-(4-phenylcyclohex-1-enyl)-1-butene
• 英文别名: N-[4-[(Z)-3,3-dimethyl-1-(4-phenylcyclohexen-1-yl)but-1-enyl]phenyl]acetamide
• 化学式: C₂₆H₃₁NO
• 分子量: 373.538
• InChiKey: PXIHPDKBGPDPBV-BWAHOGKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-phenylcyclohex-1-enyl trifluoromethanesulfonate 、 1-(p-acetamidophenyl)-3,3-dimethyl-1-butyne 在 palladium diacetate potassium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以94%的产率得到(Z)-1-(p-acetamidophenyl)-3,3-dimethyl-1-(4-phenylcyclohex-1-enyl)-1-butene
  参考文献：
  名称：

  钯催化乙烯基三氟甲磺酸与炔烃的氢乙烯基化 3-乙烯基呋喃-2(5H)-酮的合成方法

  摘要：

  在催化量的 Pd(OAc)2 和 HCOOK 存在下，炔烃与乙烯基三氟甲磺酸酯的反应，省略磷烷配体，通常以良好到高产率提供加氢乙烯基化产物。该反应已被用于从 4-羟基-2-丁酸甲酯开发 3-乙烯基呋喃-2(5H)-酮的区域选择性合成。

  DOI：

  10.1002/(sici)1099-0690(199912)1999:12<3305::aid-ejoc3305>3.0.co;2-o

文献信息

• The Mechanism of the Phosphine-Free Palladium-Catalyzed Hydroarylation of Alkynes
  作者：Mårten Ahlquist、Giancarlo Fabrizi、Sandro Cacchi、Per-Ola Norrby

  DOI：10.1021/ja061543x

  日期：2006.10.1

  The mechanism of the Pd-catalyzed hydroarylation and hydrovinylation reaction of alkynes has been studied by a combination of experimental and theoretical methods (B3LYP), with an emphasis on the phosphine-free version. The regioselectivity of the hydroarylation and hydrovinylation shows unexpected differences, which could be attributed mainly to the higher steric demand of the cyclohexenyl group as compared to the phenyl group. Hydroarylation of alpha,beta-acetylenic carbonyl substrates yields a very unusual anti-Michael selectivity, which is shown to result from reaction of the nonconjugated double bond, leaving the conjugation intact. In all cases were the regioselectivities reproduced by the calculations.