(1R,2S)-2-methyl-indan-1,2-diol | 56588-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,2S)-2-methyl-indan-1,2-diol
• 英文别名: 2,3-Dihydro-2-methyl-1H-indene-1,2-diol (cis)；(1R,2S)-2-methyl-1,3-dihydroindene-1,2-diol
• CAS: 56588-40-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: MKARJBDVTHBYRH-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基茚 在 (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)rhodium (I) 、 (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline 双联邻苯二酚硼酸酯 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以17%的产率得到(1R,2S)-2-methyl-indan-1,2-diol
  参考文献：
  名称：

  [EN] CATALYZED ENANTIOSELECTIVE TRANSFORMATION OF ALKENES
  [FR] TRANSFORMATION ENANTIO-SELECTIVE CATALYSEE D'ALCENES

  摘要：

  公开号：

  WO2005012209A3

文献信息

• Rh-Catalyzed Enantioselective Diboration of Simple Alkenes:  Reaction Development and Substrate Scope
  作者：Stéphane Trudeau、Jeremy B. Morgan、Mohanish Shrestha、James P. Morken

  DOI：10.1021/jo051651m

  日期：2005.11.1

  The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
• Rhodium-Catalyzed Enantioselective Diboration of Simple Alkenes
  作者：Jeremy B. Morgan、Steven P. Miller、James P. Morken

  DOI：10.1021/ja035851w

  日期：2003.7.1

  Enantioselective catalytic reactions that operate directly on inexpensive unactivated alkenes are extraordinarily useful for the preparation of chiral organic building blocks and new materials. While a number of such processes have been developed, our ability to meet the intensifying demand for inexpensive stereochemically complex materials will require a significant expansion of practical catalytic asymmetric reaction methodology. In this regard, the rhodium-catalyzed enantioselective diboration reaction has been developed in order to address a number of extant problems in catalytic alkene transformation simultaneously. This process provides an enantiomerically enriched reactive dimetalated intermediate which can be converted to a variety of difunctional reaction products.