(±)-ethyl 6-phenylhexa-2,3-dienoate | 1422199-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (±)-ethyl 6-phenylhexa-2,3-dienoate
• CAS: 1422199-48-1
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: MSYDAZKXRPEFOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (E)-1-acetyl-2,3-dihydro-3-(2-phenylmethylene)-2H-indol-2-one 、 (±)-ethyl 6-phenylhexa-2,3-dienoate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以65%的产率得到ethyl 1'-acetyl-2'-oxo-5-phenethyl-2-phenylspiro[cyclopent[3]ene-1,3'-indoline]-3-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

  摘要：

  The phosphine-promoted [3 + 2] cyclizations between gamma-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh3 operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

  DOI：

  10.1021/jo302460d

文献信息

• Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates
  作者：Haile Qiu、Xiaofeng Chen、Junliang Zhang

  DOI：10.1039/c9sc04073k

  日期：——

  A novel class of bifunctional cyclic phosphine catalysts (Le-Phos) is reported, which showed good performances in enantioselective γ-addition reactions of N-centered nucleophiles and allenoates under mild conditions.

  一种新型的双功能环磷催化剂（Le-Phos）被报道，它在温和条件下对N-中心亲核试剂和烯酸酯的对映选择性γ-加成反应中表现出良好的性能。
• Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ-Substituted Allenes and Electron-Poor Olefins
  作者：Maxime Gicquel、Yang Zhang、Paul Aillard、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1002/anie.201500299

  日期：2015.4.27

  The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene‐ or alkylidenemalononitriles and γ‐substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses

  报道了在非对映选择性的有机催化中首次使用磷烯。已经制备了新的手性磷杂环烯，它们可以使亚芳基或亚烷基烯丙二腈与γ-取代的烯丙酸酯或氰基烯丙烯之间进行高度对映选择性的[3 + 2]环化反应。这些反应以高收率和非对映选择性提供环戊烯衍生物，对映体过量高达97％。
• Catalytic Asymmetric CN Bond Formation: Phosphine-Catalyzed Intra- and Intermolecular γ-Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates
  作者：Rylan J. Lundgren、Ashraf Wilsily、Nicolas Marion、Cong Ma、Ying Kit Chung、Gregory C. Fu

  DOI：10.1002/anie.201208957

  日期：2013.2.25

  Pin the amine on the gamma: A new method has been developed for the γ‐addition of nitrogen nucleophiles to γ‐substituted alkynoates or allenoates through intra‐ and intermolecular processes that are catalyzed by spirophosphine 1 (see scheme). An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ‐amino‐α,β‐unsaturated carbonyl compounds.

  将胺固定在 γ 上：已经开发出一种新方法，通过由螺膦1催化的分子内和分子间过程，将氮亲核试剂 γ 加成到 γ 取代的炔酸酯或烯丙酸酯上（参见方案）。该反应的不对称形式提供了对映体富集的吡咯烷、二氢吲哚和 γ-氨基-α,β-不饱和羰基化合物。