(1E,4E)-1-(4-chlorophenyl)-5-phenypenta-1,4-dien-3-one | 68386-89-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1-(4-chlorophenyl)-5-phenypenta-1,4-dien-3-one
• 英文别名: 1-phenyl-5-(4-chlorophenyl)pentadien-3-one；1t-(4-chloro-phenyl)-5t-phenyl-penta-1,4-dien-3-one；1t-(4-Chlor-phenyl)-5t-phenyl-penta-1,4-dien-3-on；5t-Phenyl-1t-(4-chlor-phenyl)-pentadien-(1.4)-on-(3)；1-(4-Chlorophenyl)-5-phenyl-1,4-pentadien-3-one；(1E,4E)-1-(4-chlorophenyl)-5-phenylpenta-1,4-dien-3-one
• CAS: 68386-89-0
• 化学式: C₁₇H₁₃ClO
• 分子量: 268.743
• InChiKey: PZAALISHZLYIHV-QHKWOANTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(4-chlorophenyl)-5-phenypenta-1,4-dien-3-one 生成 2-(4-Chlorophenyl)-6-phenylthian-4-one
  参考文献：
  名称：

  WEBER, K. -H.;SCHNEIDER, C.;WALTHER, G.;POOK, K. -H.;BOEKE, K.;BECHTEL, W+

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 苄叉丙酮 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以87%的产率得到(1E,4E)-1-(4-chlorophenyl)-5-phenypenta-1,4-dien-3-one
  参考文献：
  名称：

  Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids

  摘要：

  In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1, x-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.027

文献信息

• Quinine-Catalysed Double Michael Addition of Malononitrile to 1,5-Disubstituted Pentadien-3-ones: A Stereoselective Route to Cyclohexanones
  作者：Claudia De Fusco、Alessandra Lattanzi

  DOI：10.1002/ejoc.201100282

  日期：2011.7

  The stereoselective synthesis of 4-oxo-2,6-diaryl-cyclohexane-1,1-dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5-disubstituted pentadien-3-ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate-to-good yields, excellent diastereoselectivity and up to 86 % ee. The isolation of the monoaddition product helps to shed light

  4-氧代-2,6-二芳基-环己烷-1,1-二腈的立体选择性合成是通过丙二腈与奎宁催化的1,5-二取代戊二烯-3-酮的双迈克尔加成而开发的。这种简单的级联过程以中等至良好的产率、出色的非对映选择性和高达 86% 的 ee 提供了环己酮。单加成产物的分离有助于阐明两步法的立体化学结果。
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