5-bromo-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one | 1364424-04-3

• 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: 5-bromo-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• 英文别名: 5-bromo-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxo-cyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydroxanthen-1-one；5-bromo-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
• CAS: 1364424-04-3
• 化学式: C₂₃H₂₄BrClO₄
• 分子量: 479.798
• InChiKey: XEADGPPNIJLMMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-溴-5-氯水杨醛 、 5,5-二甲基-1,3-环己二酮 在 1,3-二氨基-2-羟基丙烷 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以76%的产率得到5-bromo-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one
  参考文献：
  名称：

  一些新的茚并[1',2':3,4]芴[1,2-d]oxonine-5,11,16,21-tetraones 和oxocyclohex-1-en-1-yl-hydro-1H-的合成xanthen-1-ones

  摘要：

  摘要 通过 1,3-茚二酮与 4-溴-2-羟基苯甲醛和/或 2-羟基-1-萘醛在 1,3-二氨基丙-2-醇存在下反应合成了新型 oxonine 2, 4。作为绿色碱性催化剂。另一方面，1,3-环己二酮与2-羟基芳香醛在相同反应条件下反应得到呫吨酮衍生物9-11。图形概要

  DOI：

  10.1080/00397911.2019.1683205

文献信息

• Bronsted acid-type biosurfactant for heterocyclization: a green protocol for benzopyran synthesis
  作者：Smita T. Morbale、Swati D. Jadhav、Madhukar B. Deshmukh、Suresh S. Patil

  DOI：10.1039/c5ra13652k

  日期：——

  Synthesis of benzopyran from the various salicylaldehydes and cyclic 1,3-diketones using catalytic amount of lemon extract as a green biosurfactant.

  使用柠檬提取物作为绿色生物表面活性剂，从各种水杨醛和环状1,3-二酮合成苯并吡喃。
• Efficient, High-Yield Protocol for the One-Pot Synthesis of Benzopyran Derivatives Catalyzed by <i>p</i>-TSA in Aqueous Media
  作者：Lingaiah Nagarapu、Shuklachary Karnakanti、Rajashaker Bantu、B. Sridhar

  DOI：10.1080/00397911.2010.533804

  日期：2012.4.1

  A short and simple synthesis of benzopyran derivatives was accomplished in good to excellent yields by the reaction of salicylaldehyde with 1,3-cyclohexanediones in aqueous media catalyzed by para-toluenesulfonic acid. The structures were established by spectroscopic data and further confirmed by x-ray analysis. In addition, water was chosen as a green solvent.
• A rapid and efficient CsF catalyzed tandem Knoevenagel–Michael reaction
  作者：Khalid Mohammed Khan、Imran Khan、Shahnaz Perveen、Muhammad Imran Malik

  DOI：10.1016/j.jfluchem.2013.11.010

  日期：2014.2

  A simple, experimentally rapid and efficient CsF catalyzed tandem Knoevenagel-Michael reaction protocol is developed for the synthesis of a series of functionalized 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (1-7) by reacting dimedone with substituted salicylaldehydes. The use of CsF as a catalyst allowed reactions under moderate conditions and resulted in better yields. (C) 2013 Elsevier B.V. All rights reserved.