2-[(1S,2R)-1-(1,3,2-benzodioxaborol-2-yl)-1-phenylpropan-2-yl]-1,3,2-benzodioxaborole | 575489-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(1S,2R)-1-(1,3,2-benzodioxaborol-2-yl)-1-phenylpropan-2-yl]-1,3,2-benzodioxaborole
• CAS: 575489-90-6
• 化学式: C₂₁H₁₈B₂O₄
• 分子量: 355.994
• InChiKey: MKEPZZHYMJMQQL-VFNWGFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(1S,2R)-1-(1,3,2-benzodioxaborol-2-yl)-1-phenylpropan-2-yl]-1,3,2-benzodioxaborole 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1R,2R)-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  Rh-Catalyzed Enantioselective Diboration of Simple Alkenes:  Reaction Development and Substrate Scope

  摘要：

  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.

  DOI：

  10.1021/jo051651m
• 作为产物：
  描述：

  甲基苯乙烯 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 作用下， 生成 2-[(1S,2R)-1-(1,3,2-benzodioxaborol-2-yl)-1-phenylpropan-2-yl]-1,3,2-benzodioxaborole
  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

• Rhodium catalysed diboration of unstrained internal alkenes and a new and general route to zwitterionic [L2Rh(η6-catBcat)] (cat = 1,2-O2C6H4) complexes†
  作者：Chaoyang Dai、Todd B. Marder、Edward G. Robins、Dmitri S. Yufit、Judith A. K. Howard、Todd B. Marder、Andrew J. Scott、William Clegg

  DOI：10.1039/a804710c

  日期：——

  Reactions of [L2Rh(acac)] (L = alkene or phosphine) with B2cat3 yield the zwitterionic complexes [L2Rh(η6-catBcat)] and [(acac)Bcat] cleanly; [(dppm)Rh(η6-catBcat)], the X-ray structure of which is reported, is an excellent catalyst for the diboration of vinylarenes and unstrained internal alkenes cis- and trans-stilbene and trans-β-methylstyrene.

  [L2Rh(acac)]（L = 烯烃或膦）与B2cat3反应生成净化的两性离子配合物[L2Rh(η6-catBcat)]和[(acac)Bcat]；其中，[(dppm)Rh(η6-catBcat)]的X射线结构已被报道，是一种优异的催化剂，用于乙烯基芳烃和不饱和内烯烃（顺式和反式二苯乙烯以及反式β-甲基苯乙烯）的二硼化反应。
• Gold(0) Nanoparticles for Selective Catalytic Diboration
  作者：Jesus Ramírez、Mercedes Sanaú、Elena Fernández

  DOI：10.1002/anie.200800541

  日期：2008.6.27
• [EN] CATALYZED ENANTIOSELECTIVE TRANSFORMATION OF ALKENES<br/>[FR] TRANSFORMATION ENANTIO-SELECTIVE CATALYSEE D'ALCENES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005012209A3

  公开（公告）日：2005-08-11
• 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.