4-(1-methyl-2-propenyl)benzonitrile | 97781-00-5

• 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: 4-(1-methyl-2-propenyl)benzonitrile
• 英文别名: 4-But-3-en-2-ylbenzonitrile
• CAS: 97781-00-5
• 化学式: C₁₁H₁₁N
• 分子量: 157.215
• InChiKey: GYUFTEYLHNNDAW-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 10 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  对苯二腈 、 (E)-but-2-en-1-yltrimethylsilane 生成 4-(1-methyl-2-propenyl)benzonitrile
  参考文献：
  名称：

  MIZUNO, KAZUHIKO;IKEDA, MUNEHIRO;OTSUJI, YOSHIO, TETRAHEDRON LETT., 1985, 26, N 4, 461-464

  摘要：

  DOI：

文献信息

• γ-Selective Cross-coupling of Potassium Allyltrifluoroborates with Aryl and 1-Alkenyl Bromides Catalyzed by a Pd(OAc)₂/D-<i>t</i>-BPF Complex
  作者：Yasunori Yamamoto、Shingo Takada、Norio Miyaura

  DOI：10.1246/cl.2006.704

  日期：2006.7

  Cross-coupling reactions of [RCH=CHCH2BF3]K with aryl or 1-alkenyl bromides occurred at the γ-carbon of an allylborane moiety with perfect regioselectivities (>99%) in the presence of a palladium/D-t-BPF complex and K2CO3 in refluxing THF.

  在钯/D-t-BPF 复合物和 K2CO3 的存在下，在回流四氢呋喃中，[RCH=CHCH2BF3]K 与芳基或 1-烯基溴的交叉偶联反应在烯丙基硼烷分子的 γ 碳上发生，具有完美的区域选择性（大于 99%）。
• Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts
  作者：Scott E. Denmark、Nathan S. Werner

  DOI：10.1021/ja805951j

  日期：2008.12.3

  The sodium salts of allyldimethylsilanol and 2-butenyldimethylsilanol undergo palladium-catalyzed cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. The coupling of both silanolates required extensive optimization to deliver the expected products in high yields. The reaction of the allyldimethylsilanolate takes place at 85 degrees C in 1,2-dimethoxyethane with allylpalladium chloride dimer (2.5 mol %) to afford 73-95% yields of the allylation products. Both electron-rich and sterically hindered bromides reacted smoothly, whereas electron-poor bromides cross-coupled in poor yield because of a secondary isomerization to the 1-propenyl isomer (and subsequent polymerization). The 2-butenyldimethylsilanolate (E/Z, 80:20) required additional optimization to maximize the formation of the branched (gamma-substitution) product. A remarkable influence of added alkenes (dibenzylideneacetone and norbornadiene) led to good selectivities for electron-rich and electron-poor bromides in 40-83% yields. However, bromides containing coordinating groups (particularly in the ortho position) gave lower, and in one case even reversed, selectivity. Configurationally homogeneous (E)-silanolates gave slightly higher gamma-selectivity than the pure (2)-silanolates. A unified mechanistic picture involving initial gamma-transmetalation followed by direct reductive elimination or sigma-pi isomerization can rationalize all of the observed trends.
• A novel photosubstitution of dicyanobenzenes by allylic and benzylic silanes
  作者：Kazuhiko Mizuno、Munehiro Ikeda、Yoshio Otsuji

  DOI：10.1016/s0040-4039(00)61911-1

  日期：1985.1