N,N-Diisopropyl-4-phenyl-3-butenamide

• 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: N,N-Diisopropyl-4-phenyl-3-butenamide
• 英文别名: (E)-N,N-diisopropyl-4-phenylbut-3-enamide；(E)-4-phenyl-N,N-di(propan-2-yl)but-3-enamide
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: WUFLNVSWNHSORF-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tri(phenylvinyl)boroxine 、 N,N-diisopropyldiazoacetamide 在 二异丙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 N,N-Diisopropyl-4-phenyl-3-butenamide
  参考文献：
  名称：

  Arylation and Vinylation of α-Diazocarbonyl Compounds with Boroxines

  摘要：

  An alternative approach for alpha-arylation and alpha-vinylation of carbonyl compounds is described: reaction between aryl- or vinylboroxines with alpha-diazocarbonyl compounds leads to the formation of alpha-arylated or alpha-vinylated carbonyl compounds under mild conditions.

  DOI：

  10.1021/ol900362d

文献信息

• (E)-β,γ-unsaturated amides from (E)-9-alkenyl-9-borabicyclo[3.3.1]nonane and N,N-dialkyl(dimethylsulfuranylidene)acetamide
  作者：Min-Zhi Deng、Nan-Sheng Li、Yao-Zeng Huang

  DOI：10.1039/c39930000065

  日期：——

  A facile route for the stereocontrolled synthesis of (E)-β,γ-unsaturated amides by the reaction of stereodefined 9-alkenyl-9-borabicyclo[3.3.1]nonane with N,N-dialkyl(dimethylsulfuranylidene)acetamide is described.

  本研究描述了通过立体定义的 9-烯基-9-硼杂双环[3.3.1]壬烷与 N,N-二烷基（二甲基亚硫酰）乙酰胺反应，立体控制合成 (E)-δ²,δ³-不饱和酰胺的简便路线。
• Ruthenium Complex-Catalyzed Carbonylation of Allylic Compounds
  作者：Take-aki Mitsudo、Nobuyoshi Suzuki、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1021/jo00104a036

  日期：1994.12

  Allylic alkyl carbonates are carbonylated under 40 atm of carbon monoxide at 100-120 degrees C in the presence of a catalytic amount of Ru-3(CO)(12)/1,10-phenanthroline to give alpha,beta- or beta,gamma-unsaturated esters in good to high yields. For example, cinnamyl methyl carbonate afforded the corresponding beta,gamma-unsaturated esters, methyl trans-4-phenyl-3-butenoate (1). in 93% yield. The regioselectivity in the carbonylation of crotyl methyl carbonate is unusual and it depends on the carbon monoxide pressure. The more sterically hindered carbon (gamma-carbon) is predominantly carbonylated at 20-50 atm. When the reaction of cinnamyl methyl carbonate was performed at elevated temperature (150 degrees C) without 1,10-phenanthroline, the dimer of 1, dimethyl 3-benzyl-2-(trans-2-phenylvinyl)glutarate, was obtained in 56% yield. In the presence of secondary amines, allylic alkyl carbonates were carbonylated mainly at alpha-carbon to give alpha,beta- or beta,gamma-unsaturated amides in high yields.