2-propyl-2H-chromene-3-carbaldehyde | 1569884-66-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2-propyl-2H-chromene-3-carbaldehyde
• CAS: 1569884-66-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YTWPANAGBRTUMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-propyl-2H-chromene-3-carbaldehyde 、 乙酰乙酸乙酯 在 sodium benzoate 、 (-)-(5aS,10bR)-5a,10b-二氢-2-(2,4,6-三甲基苯基)-4H,6H-茚并[2,1-b][1,2,4]三唑[4,3-d][1,4]氯化恶唑鎓一水合物 、 3,3',5,5'-四叔丁基-4,4'-联苯醌 作用下， 以 四氢呋喃 为溶剂， 以16%的产率得到ethyl (5R)-2-methyl-4-oxo-5-propyl-4a,10b-dihydro-4H,5H-pyrano[3,4-c]chromene-1-carboxylate
  参考文献：
  名称：

  NHC催化动力学拆分不对称合成具有三个连续立体中心的二氢吡喃酮

  摘要：

  已开发出 NHC 催化合成具有三个连续立体中心的三环二氢吡喃酮。对该机制的研究表明，决定速率的步骤是 Breslow 中间体形成。

  DOI：

  10.1002/ejoc.202100491
• 作为产物：
  描述：

  2-已烯醛 、 水杨醛 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 neat (no solvent) 为溶剂， 反应 48.0h， 以88%的产率得到2-propyl-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  A solvent-free protocol for the synthesis of 3-formyl-2H-chromenes via domino oxa Michael/aldol reaction

  摘要：

  A new solvent-free, TBD-catalyzed protocol for the synthesis of 3-formyl-2H-chromenes is presented. Substituted salicylaldehydes 1 and 3-methyl-2-butenal 2 in the presence of 10 mol % of TBD underwent a domino oxa Michael/aldol reaction to effectively yield the corresponding 2H-chromene derivatives 3. The methodology represents an improvement either in terms of efficiency and sustainability as a small amount of catalyst is required and the work-up procedure is simple and straightforward. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.110

文献信息

• A solvent-free protocol for the synthesis of 3-formyl-2H-chromenes via domino oxa Michael/aldol reaction
  作者：Daniela Lanari、Ornelio Rosati、Massimo Curini

  DOI：10.1016/j.tetlet.2014.01.110

  日期：2014.3

  A new solvent-free, TBD-catalyzed protocol for the synthesis of 3-formyl-2H-chromenes is presented. Substituted salicylaldehydes 1 and 3-methyl-2-butenal 2 in the presence of 10 mol % of TBD underwent a domino oxa Michael/aldol reaction to effectively yield the corresponding 2H-chromene derivatives 3. The methodology represents an improvement either in terms of efficiency and sustainability as a small amount of catalyst is required and the work-up procedure is simple and straightforward. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
  作者：Anton Axelsson、Mathias Westerlund、Savannah C. Zacharias、August Runemark、Matti Haukka、Henrik Sundén

  DOI：10.1002/ejoc.202100491

  日期：2021.7.7

  An oxidative NHC-catalyzed synthesis of tricyclic dihydropyranones with three contiguous stereocenters has been developed. Studies of the mechanism suggest that the rate-determining step is the Breslow intermediate formation.

  已开发出 NHC 催化合成具有三个连续立体中心的三环二氢吡喃酮。对该机制的研究表明，决定速率的步骤是 Breslow 中间体形成。