(E)-7-(diethylamino)-3-(3-(2-hydroxyphenyl)acryloyl)-2Hchromen-2-one | 1333388-46-7

• 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: (E)-7-(diethylamino)-3-(3-(2-hydroxyphenyl)acryloyl)-2Hchromen-2-one
• 英文别名: 7-(diethylamino)-3-[(E)-3-(2-hydroxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 1333388-46-7
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: WJNDEZGHZZMTLN-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 (E)-7-(diethylamino)-3-(3-(2-hydroxyphenyl)acryloyl)-2Hchromen-2-one 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction

  摘要：

  Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.002
• 作为产物：
  描述：

  水杨醛 、 3-乙酰基-7-二乙基氨基-2H-色烯-2-酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以40%的产率得到(E)-7-(diethylamino)-3-(3-(2-hydroxyphenyl)acryloyl)-2Hchromen-2-one
  参考文献：
  名称：

  Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction

  摘要：

  Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.002

文献信息

• Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction
  作者：Hyun-Joon Ha、Doo-Ha Yoon、Seokan Park、Hae-Jo Kim

  DOI：10.1016/j.tet.2011.08.002

  日期：2011.10

  Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.