苯,[[(2,2-二甲基-3-丁烯基)氧代]甲基]- | 112482-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯,[[(2,2-二甲基-3-丁烯基)氧代]甲基]-
• 英文名称: 1-((2,2-dimethylbut-3-enyloxy)methyl)benzene
• 英文别名: 2,2-Dimethylbut-3-enoxymethylbenzene
• CAS: 112482-46-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: IRXBIEJRQYLBFA-UHFFFAOYSA-N

物化性质

• 沸点：
  245.3±19.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-(苄氧基)-2,2-二甲基-1-丙醇	3-(benzyloxy)-2,2-dimethylpropan-1-ol	66582-32-9	C12H18O2	194.274

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-4-benzyloxy-3,3-dimethyl-butane-1,2-diol	104708-09-0	C13H20O3	224.3

反应信息

• 作为反应物：
  描述：

  苯,[[(2,2-二甲基-3-丁烯基)氧代]甲基]- 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 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以71%的产率得到(R)-4-benzyloxy-3,3-dimethyl-butane-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
• 作为产物：
  描述：

  3-(苄氧基)-2,2-二甲基-1-丙醇 、 三甲基硅烷化重氮甲烷 在 1,10-菲罗啉 、 potassium tert-butylate 、 copper(l) chloride 、 N-甲基咪唑 、 偶氮二甲酸二叔丁酯 、 氧气 、 三苯基膦 、 异丙醇 作用下， 以 氟苯 、 乙醚 为溶剂， 反应 0.17h， 以81%的产率得到苯,[[(2,2-二甲基-3-丁烯基)氧代]甲基]-
  参考文献：
  名称：

  Copper-Catalyzed Tandem Oxidation−Olefination Process

  摘要：

  A novel catalytic sequence aerobic oxidation-olefination has been developed. A single and inexpensive copper,catalyst provides a large range of olefins from alcohols In good to excellent yields. The reaction exhibits excellent functional group compatibility, and the nonbasic reaction conditions allow the transformation of chiral substrates without racemization.

  DOI：

  10.1021/ol802299d

文献信息

• [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
• Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction
  作者：Steven P. Miller、Jeremy B. Morgan、Nepveux、James P. Morken

  DOI：10.1021/ol036219a

  日期：2004.1.1

  Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C-B bond participates in cross-coupling. The remaining C-B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.
• Copper-Catalyzed Tandem Oxidation−Olefination Process
  作者：Michaël Davi、Hélène Lebel

  DOI：10.1021/ol802299d

  日期：2009.1.1

  A novel catalytic sequence aerobic oxidation-olefination has been developed. A single and inexpensive copper,catalyst provides a large range of olefins from alcohols In good to excellent yields. The reaction exhibits excellent functional group compatibility, and the nonbasic reaction conditions allow the transformation of chiral substrates without racemization.
• 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.