2,4-diphenylpent-4-enenitrile | 1314894-77-3

• 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: 2,4-diphenylpent-4-enenitrile
• 英文别名: 2,4-Diphenylpent-4-enenitrile
• CAS: 1314894-77-3
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: AYPKLZZHUDWMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,4-diphenylpent-4-enenitrile 在 正丁基锂 、 (4R,5R)-2-chloro-3,4-dimethyl-2-[(2-methylpropan-2-yl)oxy]-5-phenyl-1,3,2-oxazasilolidine 、 二异丙胺 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 为溶剂， 反应 23.17h， 生成 C₃₂H₂₆F₃N₃O 、 C₃₂H₂₆F₃N₃O
  参考文献：
  名称：

  A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

  摘要：

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.

  DOI：

  10.1021/ol201566u
• 作为产物：
  描述：

  苯乙腈 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 33.17h， 生成 2,4-diphenylpent-4-enenitrile
  参考文献：
  名称：

  A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

  摘要：

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.

  DOI：

  10.1021/ol201566u

文献信息

• 10.1021/jacs.4c04370
  作者：Zheng, Yu、Dong, Qi-Xin、Wen, Shu-Ya、Ran, Hui、Huang, Huan-Ming

  DOI：10.1021/jacs.4c04370

  日期：——

  unprecedented di-π-ethane rearrangement enabled by energy-transfer catalysis under visible light conditions. This innovative open-shell rearrangement boasts broad tolerance toward a range of functional groups, encompassing even complex drug and natural product derivatives. Overall, the reported di-π-ethane rearrangement represents a complementary strategy to the development of radical translocation enabled

  分子重排在合成化学的基本转变中占据着举足轻重的地位。自由基易位已成为一种流行的合成工具，有效促进不同官能团的迁移。相比之下，二-π-甲烷重排的发展仍然有限，特别是在氰基官能团的易位方面。这主要归因于能量上不利的三元环过渡态。在此，我们介绍了在可见光条件下通过能量转移催化实现的前所未有的二π乙烷重排。这种创新的开壳重排对一系列官能团具有广泛的耐受性，甚至包括复杂的药物和天然产物衍生物。总体而言，所报道的二-π-乙烷重排代表了能量转移催化实现的自由基易位发展的补充策略。
• (2-Cyano-2-(phenyl or naphthyl)-2-substituted-ethyl) pyrazines, pyrimidines and pyridazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0276920B1

  公开（公告）日：1991-04-03
• Catalytic α-Monoallylation of Aryl Acetonitriles
  作者：Tapan Maji、Jon A. Tunge

  DOI：10.1021/ol5024294

  日期：2014.10.3

  alpha-Cyano aldehydes undergo selective transition-metal-catalyzed monoallylation to provide alpha-allylated nitriles. The transformation leads to linear substitution products with palladium catalysts or branched allylated nitriles using an iridium catalyst. Facile TBD-catalyzed retro-Claisen cleavage is leveraged to attain selective monoallylation.
• A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence
  作者：Jenny M. Baxter Vu、James L. Leighton

  DOI：10.1021/ol201566u

  日期：2011.8.5

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.