反式-3-苯甲酰基-1,3-二苯基-1-丙烯 | 252027-83-1

• 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
• 中文名称: 反式-3-苯甲酰基-1,3-二苯基-1-丙烯
• 英文名称: trans-3-benzoyl-1,3-diphenyl-1-propene
• 英文别名: 1,3-diphenyl-2-propenyl benzoate；[(E)-1,3-diphenylprop-2-enyl] benzoate
• CAS: 252027-83-1
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: RYCKHWLYZDSKSJ-WUKNDPDISA-N

物化性质

• 沸点：
  474.4±24.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-3-苯甲酰基-1,3-二苯基-1-丙烯 在 苯基三乙氧基硅烷 、 四丁基氟化铵 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 1,1,3,-triphenyl-1-propene
  参考文献：
  名称：

  Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

  摘要：

  Palladium-catalyzed cross-coupling of hypervalent arylsiloxane derivatives proceeded in good to excellent yields with allylic benzoates. Arylation occurred with complete inversion of configuration. The scope and limitations of this reaction, an alternative to the Stille coupling, is summarized.

  DOI：

  10.1021/jo010627f
• 作为产物：
  描述：

  trans-4,4'-dimethylchalcone 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 反式-3-苯甲酰基-1,3-二苯基-1-丙烯
  参考文献：
  名称：

  钯催化吲哚不对称 N-烷基化的轴向手性苯乙烯-膦配体

  摘要：

  使用新型轴向手性苯乙烯-膦配体SJTU-PHOS-1开发了一种高效的钯催化吲哚对映选择性直接N-烷基化反应。该反应在温和条件下表现出良好的官能团相容性和广泛的底物范围。此外，DFT计算阐述了金属催化剂与轴向手性苯乙烯-膦配体在对映选择性控制中的配位模式。

  DOI：

  10.1021/acs.joc.3c01734

文献信息

• Kinetic resolution of allylic esters in palladium-catalyzed asymmetric allylic alkylations using C–N bond axially chiral aminophosphine ligands
  作者：Takashi Mino、Kazuya Wakui、Shunsuke Oishi、Youtaro Hattori、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetasy.2008.11.026

  日期：2008.12

  Chiral allylic esters, such as (R)-1,3-diphenyl-2-propenyl acetate (R)-2a, were synthesized by kinetic resolution in a palladium-catalyzed asymmetric allylic alkylation using N-aryl indoline type C–N bond axially chiral aminophosphines (S)-1 as ligands.

  手性烯丙基酯，如（- [R）-1,3-二苯基-2-丙烯基乙酸酯（- [R ）-图2a中，通过动力学拆分以合成的钯-催化的不对称烯丙基烷基化使用ñ -芳基二氢吲哚型C-N键的轴向手性氨基膦（S）-1作为配体。
• Preparation of quarternary ammonium salt-tagged ferrocenylphosphine-imine ligands and their application to palladium-catalyzed asymmetric allylic substitution
  作者：Hao Yuan、Zhiming Zhou、Jiangliang Xiao、Lixuan Liang、Li Dai

  DOI：10.1016/j.tetasy.2010.05.047

  日期：2010.8

  A series of novel quarternary ammonium salt-modified chiral ferrocenylphosphine-imine ligands have been synthesized and the molecular structure of BIT5 has been determined by single-crystal X-ray diffraction. The applicability of these ligands in asymmetric C*-C and C*-N bond formation was demonstrated. High enantioselectivity was obtained in the Pd-catalyzed asymmetric substitution of 1,3-diphenyl-2-propenyl acetate, with dimethyl malonate (up to 94.6% ee) and benzylamine (up to 92.6% ee). (C) 2010 Published by Elsevier Ltd.
• Ionic-salt-tagged ferrocenyl diphosphine–imine ligands and their application to palladium-catalyzed asymmetric allylic etherification
  作者：Li Dai、Xin Li、Hao Yuan、Xia Li、Zhihuai Li、Di Xu、Fan Fei、Yingqiang Liu、Jun Zhang、Zhiming Zhou

  DOI：10.1016/j.tetasy.2011.07.025

  日期：2011.7

  A new type of ferrocenyl diphosphine-imine ligands that contains an ionic salt group has been prepared, and successfully applied to asymmetric C*-O bond formation. In the Pd-catalyzed asymmetric allylic etherification of 1,3-diphenyl-2-propenyl acetate, high enantioselectivity was obtained (up to 91.0% ee). The potential of the catalysts to be recycled and reused has also been demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.
• Kinetic resolution in Pd-catalyzed allylic substitution using the helical PHelix ligand
  作者：Manfred T Reetz、Stefan Sostmann

  DOI：10.1016/s0022-328x(00)00173-x

  日期：2000.5

  The chiral helical diphosphine 2,1 5-bis(diphenylphosphino)-hexahelicene (PHelix) is an excellent ligand in palladium catalyzed kinetic resolution involving allylic substitution. Depending upon the substrate, enantioselectivities (ee) of up to 99% are observed. Although formally a diphosphine, PHelix appears not to undergo chelation, which means that it behaves as a chiral monophosphine. (C) 2000 Published by Elsevier Science S.A. All rights reserved.
• Palladium-Catalyzed Allylic Substitution: Reversible Formation of Allyl-Bridged Dinuclear Palladium(I) Complexes
  作者：Christian Markert、Markus Neuburger、Klaus Kulicke、Markus Meuwly、Andreas Pfaltz

  DOI：10.1002/anie.200701248

  日期：2007.8.3