2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentanone
• 英文别名: 2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentan-1-one；2-acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentan-1-one
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: ZGEGTRZHIDWGNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium disulfite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 以191 mg的产率得到2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentanone
  参考文献：
  名称：

  An Organocatalytic Oxidative Coupling Strategy for the Direct Synthesis of Arylated Quaternary Stereogenic Centers

  摘要：

  A broadly applicable oxidative coupling strategy of 3-substituted catechols and carbon-centered pro-nucleophiles for the construction of arylated quaternary stereogenic centers has been developed. Pivoting on a base-catalyzed addition of a carbon-centered acid to an in situ generated o-benzoquinone, the method is general and atom-economical and provides remarkably efficient access to one of the most challenging structural motifs. Furthermore, use of chiral bifunctional organocatalysts allows the process to be rendered asymmetric (up to 81% ee).

  DOI：

  10.1021/ol702277v

文献信息

• Kinetic study of electrochemically induced Michael reactions ofo-benzoquinones with 2-acetylcyclohexanone and 2-acetylcyclopentanone
  作者：Davood Nematollahi、Mohammad Alimoradi、Mohammad Rafiee

  DOI：10.1002/poc.1125

  日期：2007.1

  The reaction of electrochemically generated o-benzoquinones (2a-f) as Michael acceptors with 2-acetylcyclohexanone (ACH) and 2-acetylcyclopentanone (ACP), as nucleophiles has been studied in various pHs using cyclic voltammetry. The results indicate that the participation of o-benzoquinones (2a-f) in the Michael reaction with acetylcyclohexanone (ACH) to form the corresponding catechol derivatives

  已经使用循环伏安法研究了在各种pH下电化学生成的作为迈克尔受体的邻苯二甲酮（2a-f）与2-乙酰基环己酮（ACH）和2-乙酰基环戊酮（ACP）的亲核反应。结果表明，邻-苯醌（2a-f）参与了与乙酰环己酮（ACH）的迈克尔反应，形成了相应的邻苯二酚衍生物（4a-f）。基于EC机制，通过将实验循环伏安响应与数字仿真结果进行比较，估算均质速率常数。版权所有©2007 John Wiley＆Sons，Ltd.
• An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
  作者：Katherine M. Bogle、David J. Hirst、Darren J. Dixon

  DOI：10.1016/j.tet.2010.04.132

  日期：2010.8

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.