(Z)-5-benzylidene-4-(4-chlorophenyl)-5H-furan-2-one | 95412-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-5-benzylidene-4-(4-chlorophenyl)-5H-furan-2-one
• 英文别名: (Z)-5-benzylidene-4-(4-chlorophenyl)furan-2(5H)-one；(5Z)-5-benzylidene-4-(4-chlorophenyl)furan-2-one
• CAS: 95412-20-7
• 化学式: C₁₇H₁₁ClO₂
• 分子量: 282.726
• InChiKey: SSUJXYYUCBKTMX-YBEGLDIGSA-N

物化性质

• 沸点：
  476.9±45.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (Z)-5-benzylidene-4-(4-chlorophenyl)-5H-furan-2-one 、 正丁胺 以 二氯甲烷 为溶剂， 以62%的产率得到5-benzyl-1-butyl-5-hydroxy-4-(4-chlorophenyl)pyrrol-2(5H)-one
  参考文献：
  名称：

  The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

  摘要：

  Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3-haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl-5H-furan-2-ones The furanones were subsequently treated with primary amines and dehydrated to the corresponding (Z)-5-benzylidene-4-arylpyrrol-2(5H)-one (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.080
• 作为产物：
  描述：

  p-chlorobenzenediazonium chloride 在 哌啶 、 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 (Z)-5-benzylidene-4-(4-chlorophenyl)-5H-furan-2-one
  参考文献：
  名称：

  Chellar, N. S.; Badovskaya, L. A.; Ignatenko, A. V., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1775 - 1779

  摘要：

  DOI：

文献信息

• Synthesis and stereochemistry of β-aryl-β-haloacroleins: useful intermediates for the preparation of (Z ) and (E )-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides
  作者：Damien Prim、Alexia Fuss、Gilbert Kirsch、Artur M. S. Silva

  DOI：10.1039/a900286c

  日期：——

  The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes and access to rubrolide derivatives from β-aryl-β-haloacroleins.

  提出了通过两种不同途径合成α-取代的β-芳基-β-卤代丙烯醛的方法。首次报道了通过NOE实验确定其立体化学。此外，我们描述了2-en-4-炔甲醛的制备方法以及从β-芳基-β-卤代丙烯醛中获得Rubrolide衍生物的方法。
• CHELLAR, N. S.;BADOVSKAYA, L. A.;IGNATENKO, A. V., ZH. ORGAN. XIMII, 1984, 20, N 9, 1944-1949
  作者：CHELLAR, N. S.、BADOVSKAYA, L. A.、IGNATENKO, A. V.

  DOI：——

  日期：——
• CHELLAR, N. S.;BADOVSKAYA, L. A.;IGNATENKO, A. I.;KAKLYUGINA, T. YA., XIMIYA I XIM. TEXNOL. VYP. 2, EREVAN, 1983, 97-101
  作者：CHELLAR, N. S.、BADOVSKAYA, L. A.、IGNATENKO, A. I.、KAKLYUGINA, T. YA.

  DOI：——

  日期：——
• The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones
  作者：John T. Gupton、Nakul Telang、Edith J. Banner、Emily J. Kluball、Kayleigh E. Hall、Kara L. Finzel、Xin Jia、Spencer R. Bates、R. Scott Welden、Benjamin C. Giglio、James E. Eaton、Peter J. Barelli、Lauren T. Firich、John A. Stafford、Matthew B. Coppock、Eric F. Worrall、Rene P.F. Kanters、Kerry Keertikar、Rebecca Osterman

  DOI：10.1016/j.tet.2010.09.080

  日期：2010.11

  Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3-haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl-5H-furan-2-ones The furanones were subsequently treated with primary amines and dehydrated to the corresponding (Z)-5-benzylidene-4-arylpyrrol-2(5H)-one (C) 2010 Elsevier Ltd All rights reserved
• Chellar, N. S.; Badovskaya, L. A.; Ignatenko, A. V., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1775 - 1779
  作者：Chellar, N. S.、Badovskaya, L. A.、Ignatenko, A. V.

  DOI：——

  日期：——