3-cyclopropylcarbonyl-2H-1-benzopyran-2-one | 140935-12-2

• 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-cyclopropylcarbonyl-2H-1-benzopyran-2-one
• 英文别名: 3-(Cyclopropanecarbonyl)chromen-2-one
• CAS: 140935-12-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: NULPXESORMRTOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyclopropylcarbonyl-2H-1-benzopyran-2-one 、 2-溴苯乙酮 在 甲基三辛基氯化铵 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 4,5-Benzo-exo-7-benzoyl-1-cyclopropylcarbonyl-3-oxa-cis-bicyclo<4.1.0>hept-4-en-2-one 、 4,5-Benzo-endo-7-benzoyl-1-cyclopropylcarbonyl-3-oxa-cis-bicyclo<4.1.0>hept-4-en-2-one
  参考文献：
  名称：

  Cyclopropanation reaction of 3-Acyl-2H-1-benzopyran-2-ones with phenacylbromide in phase transfer systems

  摘要：

  3-Acyl-2H-1-benzopyran-2-ones 1 reacted with phenacylbromide in the presence of a base to give the cyclopropane derivatives 2 and 3 in moderate yields. The yields of the reaction products were substantially improved by using a catalyst (Aliquat 336 or TPBP) under phase-transfer conditions. A mechanistic explanation is given for the stereoselectivity of these reactions. Spectroscopic data for compounds 2 and 3 are also given.

  DOI：

  10.1016/s0040-4020(01)80371-9

文献信息

• Potassium Fluoride Promoted Reaction of 3-Acylsubsti-Tuted 2H-1-Benzopyran-2-Ones with Acid Anhydrides. An Improved Method for the Synthesis of 4-(2-Oxoalkyl)-2H-Chroman-2-Ones. Part III¹
  作者：Anka Bojilova、Nestor A. Rodics、Rozitsa Nikolova、Christo Ivanov

  DOI：10.1080/00397919208019275

  日期：1992.3

  Abstract The reaction of 3-acylsubstituted 2H-1-benzo-pyran-2-ones 1, 5 and 11a-c with acid anhydrides in the presence of potassium fluoride (KF)/molecular sieves 4A gives the 4-(2-oxoalkyl)-2-oxochromans 2, 6 and 12a-c as the main products. Also the 3-carboxylic acid derivatives, such as esters and N,N-dialkylamides, of 2H-1-benzopyran-2-one (11d-g) react with isobutyric acid anhydride in the presence

  摘要 在氟化钾 (KF)/分子筛 4A 存在下，3-酰基取代的 2H-1-苯并-吡喃-2-酮 1、5 和 11a-c 与酸酐反应得到 4-(2-氧代烷基) -2-oxochromans 2, 6 和 12a-c 作为主要产物。此外，2H-1-苯并吡喃-2-酮 (11d-g) 的 3-羧酸衍生物，例如酯和 N,N-二烷基酰胺，在 KF/分子筛 4A 存在下与异丁酸酐反应，得到相应的 2-oxochroman-4-乙酸衍生物。
• Regio- and stereo-selective 1,3-dipolar cycloaddition reactions of ethyl diazoacetate to 3-substituted 2H-1-benzopyran-2-ones.
  作者：Anka Bojilova、I Videnova、Christo Ivanov、Nestor A Rodios、A Terzis、C.P Raptopoulou

  DOI：10.1016/s0040-4020(01)81220-5

  日期：1994.1

  The cycloaddition of ethyl diazoacetate to 3-substituted 2H-1-benzopyran-2-ones, 1, gave the benzopyrano[3,4][2]pyrazolines 11, the benzopyrano[3,4]cyclopropanes 12, the benzopyrano[3,4-c]pyrazole 13 and the (o-hydroxy)phenyl-pyrazoles 14 as the main products. When the cycloaddition was performed in the presence of silica gel the rate of the reaction increased substantially and the yields of the cyclopropane derivatives 12 were more than doubled Ethyl diazoacetate adds to benzopyran-3,4-double bond regio- and stereo-selectively giving the endo-form of the initial cycloadduct 15, which being unstable, is then transformed mainly to the above mentioned compounds.