4-(3-hydroxyprop-1-en-2-yl)benzonitrile | 46084-11-1

• 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: 4-(3-hydroxyprop-1-en-2-yl)benzonitrile
• CAS: 46084-11-1
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: OTLSGGFPZKCSMD-UHFFFAOYSA-N

物化性质

• 沸点：
  332.7±30.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxyprop-1-en-2-yl)benzonitrile 在 四溴化碳 、 三苯基膦 、 sodium azide 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 4-(3-Aminoprop-1-en-2-yl)benzonitrile
  参考文献：
  名称：

  Enantioselective Bromocyclization of Allylic Amides Catalyzed by BINAP Derivatives

  摘要：

  A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.

  DOI：

  10.1021/acs.orglett.5b00220
• 作为产物：
  描述：

  4-溴苯腈 、 2-丙炔-1-醇 在 碘 、 magnesium 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 生成 4-(3-hydroxyprop-1-en-2-yl)benzonitrile
  参考文献：
  名称：

  Enantioselective Bromocyclization of Allylic Amides Catalyzed by BINAP Derivatives

  摘要：

  A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.

  DOI：

  10.1021/acs.orglett.5b00220

文献信息

• Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles
  作者：Xiaolei Huang、Minh Hieu Nguyen、Maoping Pu、Luoqiang Zhang、Yonggui Robin Chi、Yun‐Dong Wu、Jianrong Steve Zhou

  DOI：10.1002/anie.202000859

  日期：2020.6.26

  Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

  在医学研究中，构象受限的氮杂双环化合物变得越来越重要。烯炔的不对称Heck双环化反应可得到具有出色对映选择性的可药用的aza [3.1.0]和aza [4.1.0]自行车。双环化后的关键有机钯物质可能被硅烷和末端炔烃捕获。
• Synthesis of Quaternary Carbon Centers via Hydroformylation
  作者：X. Sun、K. Frimpong、K. L. Tan

  DOI：10.1021/ja1036226

  日期：2010.9.1

  application of hydroformylation to the synthesis of quaternary carbon centers is reported. The synthesis of the highly substituted carbon is achieved by applying a catalytic amount of 1. Ligand 1 serves as a catalytic directing group by covalently and reversibly binding to both the substrate and catalyst. The intramolecular nature of the directing group strategy accelerates the hydroformylation reaction

  报道了加氢甲酰化在合成季碳中心中的应用。高度取代的碳的合成是通过施加催化量的 1 来实现的。配体 1 通过与底物和催化剂共价且可逆地结合作为催化导向基团。导向基团策略的分子内性质加速了加氢甲酰化反应，使得反应在温和的温度（35-55 摄氏度）下进行，并具有出色的区域选择性（b:l > 94:6）。