2,3-dihydro-3-hydroxy-2-methylinden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,3-dihydro-3-hydroxy-2-methylinden-1-one
• 英文别名: (2R,3S)-3-hydroxy-2-methylindanone；(2S,3R)-3-hydroxy-2-methyl-2,3-dihydroinden-1-one
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: AJGXUROZMCIZIY-IMTBSYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-propionylbenzaldehyde 在 dl-β-phenyl-α-alanine, potassium salt 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以80%的产率得到
  参考文献：
  名称：

  Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

  摘要：

  First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spiro-cyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.077

文献信息

• Application of the Intramolecular Isomerisation–Aldolisation from Allylic Alcohols and Allylic Silyl Ethers to the Synthesis of Indanones and Indenones
  作者：Julien Petrignet、Thierry Roisnel、René Grée

  DOI：10.1002/chem.200700613

  日期：2007.9.7

  A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.

  通过一步一步的镍或铁介导的2-羟基异苯并呋喃的置换发现了茚满酮的新途径。从相应的甲硅烷基醚开始，还开发了一种新的一锅式串联异构化-Mukaiyama羟醛工艺。这些多用途的策略对于制备各种类型的茚满酮和茚满酮将是有用的。