2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile | 1174070-12-2

• 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: 2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile
• 英文别名: (E)-2-(3-phenyl-prop-2-en-1-yl)benzonitrile；2-cinnamylbenzonitrile；2-[(E)-3-phenylprop-2-enyl]benzonitrile
• CAS: 1174070-12-2
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: PGWQWMPUHJVBEE-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile 在 碳酸氢钠 、 间氯过氧苯甲酸 、 sodium sulfite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.33h， 以90%的产率得到(+/-)-2-{[(2S,3S)-3-phenyloxiran-2-yl]methyl}benzonitrile
  参考文献：
  名称：

  A Cascade Approach to Cyclic Aminonitrones: Reaction Discovery, Mechanism, and Scope

  摘要：

  Treatment of omega-epoxynitriles with hydroxylamine affords cyclic aminonitrones in a single step and with high stereoselectivity. The scope of this novel transformation was explored in a series of examples. The aminonitrone products were shown to be useful substrates for further selective elaboration.

  DOI：

  10.1021/ol9010147
• 作为产物：
  描述：

  2-碘氰基苯 、 肉桂基溴 在 lithium chloro-isopropyl-magnesium chloride 、 copper(l) cyanide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以67%的产率得到2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile
  参考文献：
  名称：

  A Cascade Approach to Cyclic Aminonitrones: Reaction Discovery, Mechanism, and Scope

  摘要：

  Treatment of omega-epoxynitriles with hydroxylamine affords cyclic aminonitrones in a single step and with high stereoselectivity. The scope of this novel transformation was explored in a series of examples. The aminonitrone products were shown to be useful substrates for further selective elaboration.

  DOI：

  10.1021/ol9010147

文献信息

• Remote Aryl Cyanation via Isocyanide–Cyanide Rearrangement on Tosylmethyl Isocyanide Derivatives
  作者：Anna Coppola、Patricia Sánchez-Alonso、David Sucunza、Carolina Burgos、Ramón Alajarín、Julio Alvarez-Builla、Marta E. G. Mosquera、Juan J. Vaquero

  DOI：10.1021/ol401433x

  日期：2013.7.5

  to a cascade reaction to give unexpected 2-substituted 2,3-dihydro-1H-indenimines which, upon treatment with t-BuOK, rearrange to 2-vinylbenzonitriles in high overall yields. This simple procedure represents a new approach to the synthesis of aromatic nitriles via isocyanide–cyanide interconversion.

  烷基甲苯磺酰基甲基异氰化物和2-溴苄基溴化物在t -BuLi存在下的反应引起级联反应，产生意想不到的2-取代的2,3-二氢-1 H-茚满胺，经t- BuOK处理后，重排到2-乙烯基苄腈的高总收率。这个简单的程序代表了一种通过异氰化物-氰化物互变合成芳族腈的新方法。
• Photoredox-Catalyzed Intermolecular Remote C–H and C–C Vinylation via Iminyl Radicals
  作者：Xu Shen、Jia-Jia Zhao、Shouyun Yu

  DOI：10.1021/acs.orglett.8b02540

  日期：2018.9.7

  C(sp3)–H and C–C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-acyl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C–C cleavage, can be vinylated with vinyl boronic acids. This

  已经实现了用乙烯基硼酸对O-酰基肟进行分子间远程C（sp 3）–H和C–C乙烯基化的统一策略。该策略通过在可见光照射下从O-酰基肟光还原生成亚胺基而实现。亚胺基自由基通过1，5-氢原子转移或CC裂解产生的碳中心自由基可以用乙烯基硼酸乙烯基化。该策略为通过C（sp 3）–H和C–C裂解进行远程官能化开辟了新途径，并为合成酮和腈的γ-乙烯基化提供了一种高效且通用的解决方案。
• Selective Cross-Coupling of Organic Halides with Allylic Acetates
  作者：Lukiana L. Anka-Lufford、Michael R. Prinsell、Daniel J. Weix

  DOI：10.1021/jo302086g

  日期：2012.11.16

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.