(E)-3-[(E)-3-phenylallylidene]chroman-4-one | 1092815-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-[(E)-3-phenylallylidene]chroman-4-one
• 英文别名: (3E)-3-[(E)-3-phenylprop-2-enylidene]chromen-4-one
• CAS: 1092815-57-0
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: UQBUVQXVBZGKTI-UJHPFZFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1,4-二硫-2,5-二醇 、 (E)-3-[(E)-3-phenylallylidene]chroman-4-one 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.83h， 以86%的产率得到
  参考文献：
  名称：

  通过磺胺-迈克尔/醛醇多级联反应轻松合成具有三个连续立体中心的螺二氢苯并二氢吡喃酮-四氢噻吩

  摘要：

  （E）-3-芳基苯并二氢吡喃-4-酮与1，4-二噻吩-2，5-二醇的新型磺胺-迈克尔/羟醛级联反应已得到开发。此方法提供了一种新的实用的和容易的方法来4'-羟基-2'-芳基-4'，5'-二氢-2' ħ -螺[色满-3,3'-噻吩] -4-酮用三个连续高产量的立体中心。该转化是原子经济的，具有良好的至优异的非对映选择性。

  DOI：

  10.1016/j.tetlet.2014.11.026
• 作为产物：
  描述：

  反式肉桂醛 、 2,3-二氢苯并吡喃-4-酮 在 磷酸 作用下， 反应 4.0h， 以80%的产率得到(E)-3-[(E)-3-phenylallylidene]chroman-4-one
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors

  摘要：

  As part of an effort to generate broad-spectrum inhibitors of rhinovirus replication, novel series of (E)-3-[(E)-3-phenylallylidene]chroman-4-ones 1a-e, (E)-3-(3-phenylprop-2-yn-1-ylidene)chroman-4-ones 2a and 2b, (Z)-3-[(E)-3-phenylallylidene]chromans 3a-e, and (E)-3-(3-phenylprop-1-en-1-yl)-2H-chromenes 4a-d were designed and synthesized. All the compounds were tested in vitro for their efficacy against infection by human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. Most of the analogues were found to be potent and selective inhibitors of both HRVs, although HRV 1B was generally more susceptible than HRV 14. Mechanism of action studies of (E)-6-chloro-3-(3-phenylprop-1-en-1-yl)-2H-chromene 4b, the most potent compound on HRV 1B infection, suggested that 4b behaves as a capsid-binder probably acting at the uncoating level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.060

文献信息

• Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions
  作者：Long Zhao、Sun Li、Lei Wang、Shun Yu、Gerhard Raabe、Dieter Enders

  DOI：10.1055/s-0036-1591995

  日期：2018.7

  domino yields and stereoselectivities. A new strategy for the N-heterocyclic carbene catalyzed asymmetric synthesis of cyclopentene-fused tetrahydroquinoline derivatives has been developed. The one-pot organocatalytic domino protocol allows a direct entry to the characteristic cyclopenta[c]tetrahydroquinoline core of many alkaloids and some potential drugs employing readily available quinolinone and enal

  摘要 已经开发出一种新的策略，用于N-杂环卡宾催化的不对称合成环戊烯稠合的四氢喹啉衍生物。一锅法有机催化多米诺协议允许直接进入许多生物碱和某些潜在药物的特征性环戊并[ c ]四氢喹啉核心，这些药物采用容易获得的喹啉酮和烯类底物，具有良好的多米诺产量和立体选择性。 已经开发出一种新的策略，用于N-杂环卡宾催化的不对称合成环戊烯稠合的四氢喹啉衍生物。一锅法有机催化多米诺协议允许直接进入许多生物碱和某些潜在药物的特征性环戊并[ c ]四氢喹啉核心，这些药物采用容易获得的喹啉酮和烯类底物，具有良好的多米诺产量和立体选择性。
• Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors
  作者：Cinzia Conti、Luca Proietti Monaco、Nicoletta Desideri

  DOI：10.1016/j.bmc.2011.10.060

  日期：2011.12

  As part of an effort to generate broad-spectrum inhibitors of rhinovirus replication, novel series of (E)-3-[(E)-3-phenylallylidene]chroman-4-ones 1a-e, (E)-3-(3-phenylprop-2-yn-1-ylidene)chroman-4-ones 2a and 2b, (Z)-3-[(E)-3-phenylallylidene]chromans 3a-e, and (E)-3-(3-phenylprop-1-en-1-yl)-2H-chromenes 4a-d were designed and synthesized. All the compounds were tested in vitro for their efficacy against infection by human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. Most of the analogues were found to be potent and selective inhibitors of both HRVs, although HRV 1B was generally more susceptible than HRV 14. Mechanism of action studies of (E)-6-chloro-3-(3-phenylprop-1-en-1-yl)-2H-chromene 4b, the most potent compound on HRV 1B infection, suggested that 4b behaves as a capsid-binder probably acting at the uncoating level. (C) 2011 Elsevier Ltd. All rights reserved.
• Facile synthesis of spiro chromanone-tetrahydrothiophenes with three contiguous stereocenters via sulfa-Michael/aldol cascade reactions
  作者：Ya-Jian Hu、Xiao-Bing Wang、Su-Yi Li、Sai-Sai Xie、Kelvin D.G. Wang、Ling-Yi Kong

  DOI：10.1016/j.tetlet.2014.11.026

  日期：2015.1

  A novel sulfa-Michael/aldol cascade reaction of (E)-3-arylidenechroman-4-ones with 1,4-dithiane-2,5-diol has been developed. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4′,5′-dihydro-2′H-spiro[chroman-3,3′-thiophen]-4-ones with three contiguous stereocenters in high yields. The transformation is atom-economic with good to excellent diastereoselectivities.

  （E）-3-芳基苯并二氢吡喃-4-酮与1，4-二噻吩-2，5-二醇的新型磺胺-迈克尔/羟醛级联反应已得到开发。此方法提供了一种新的实用的和容易的方法来4'-羟基-2'-芳基-4'，5'-二氢-2' ħ -螺[色满-3,3'-噻吩] -4-酮用三个连续高产量的立体中心。该转化是原子经济的，具有良好的至优异的非对映选择性。