3-(2-hydroxyethyl)-2H-chromen-2-one | 20972-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(2-hydroxyethyl)-2H-chromen-2-one
• 英文别名: 3-(2-Hydroxyethyl)-cumarin；3-(2-hydroxy-ethyl)-chromen-2-one；3-(2-Hydroxyethyl)chromen-2-one
• CAS: 20972-50-3
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: AMCRIDPNWRYVJI-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C
• 沸点：
  378.1±22.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyethyl)-2H-chromen-2-one 在 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以98%的产率得到3-(2-溴乙基)香豆素
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032
• 作为产物：
  描述：

  3-(2-((tert-butyldimethylsilyl)oxy)ethyl)coumarin 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以91%的产率得到3-(2-hydroxyethyl)-2H-chromen-2-one
  参考文献：
  名称：

  锌（II）催化的亚酰胺和水杨醛一锅法合成香豆素

  摘要：

  已经开发了在Zn（II）催化剂存在下由酰胺和水杨醛高效高效地直接合成各种取代的香豆素的方法。在此过程中，成功地将了酰胺的磺酰胺部分进行了再循环，在形成键的过程中，它是有效的无痕导向基团，具有很高的区域选择性。该方案的优点是良好的官能团耐受性，宽泛的底物范围，简单且高产率的反应，磺酰胺的回收/重复使用，廉价催化剂的低催化剂负载量以及这些优点，使该方法更具成本效益且更环保。

  DOI：

  10.1021/acs.orglett.9b01181

文献信息

• Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
  申请人：Chen Gong

  公开号：US20080194522A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测单胺氧化酶活性的化合物，用于竞争性抑制单胺氧化酶的化合物，用于确定单胺氧化酶抑制剂和用于治疗与单胺氧化酶相关的神经系统病理的化合物，以及制药组合物和制造方法。
• FERULIC ACID AND P-COUMARIC ACID BASED POLYMERS AND COPOLYMERS
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20190002630A1

  公开（公告）日：2019-01-03

  A cinnamic acid polymer or copolymer that can be employed as a biorenewable alternative to a commodity polymer results from the polymerization of hydroxyalkyldihydroferulic acids, hydroxyalkylferulic acids, hydroxyalkyldihydrocoumaric acids, hydroxyalkylcoumaric acids, dihydroferulic acid, ferulic acid, dihydrocoumaric acid, and coumaric acid in various proportions. The physical properties of the plastic are controlled by the composition of the polymers. A melt polycondensation route achieves the desired plastics.
• [EN] DEVELOPMENT OF FLUOROGENIC SUBSTRATES FOR MONOAMINE OXIDASES (MAO-A AND MAO-B)<br/>[FR] MISE AU POINT DE SUBSTRATS FLUOROGENES DESTINES AUX MONOAMINE OXYDASES (MAO-A AND MAO-B)
  申请人：TRUSTEES OF COLLUMBIA UNIVERSI

  公开号：WO2006026368A2

  公开（公告）日：2006-03-09

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.
• [EN] FERULIC ACID AND P-COUMARIC ACID BASED POLYMERS AND COPOLYMERS<br/>[FR] POLYMÈRES ET COPOLYMÈRES À BASE D'ACIDE FÉRULIQUE ET D'ACIDE P-COUMARIQUE
  申请人：UNIV FLORIDA

  公开号：WO2017123587A1

  公开（公告）日：2017-07-20

  A cinnamic acid polymer or copolymer that can be employed as a biorenewable alternative to a commodity polymer results from the polymerization of hydroxyalkyldihydroferulic acids, hydroxyalkylferulic acids, hydroxyalkyldihydrocoumaric acids, hydroxyalkylcoumaric acids, dihydroferulic acid, ferulic acid, dihydrocoumaric acid, and coumaric acid in various proportions. The physical properties of the plastic are controlled by the composition of the polymers. A melt polycondensation route achieves the desired plastics.
• Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
  作者：Huen Ji Yoo、So Won Youn

  DOI：10.1021/acs.orglett.9b01181

  日期：2019.5.3

  A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional

  已经开发了在Zn（II）催化剂存在下由酰胺和水杨醛高效高效地直接合成各种取代的香豆素的方法。在此过程中，成功地将了酰胺的磺酰胺部分进行了再循环，在形成键的过程中，它是有效的无痕导向基团，具有很高的区域选择性。该方案的优点是良好的官能团耐受性，宽泛的底物范围，简单且高产率的反应，磺酰胺的回收/重复使用，廉价催化剂的低催化剂负载量以及这些优点，使该方法更具成本效益且更环保。