(+/-)-α-pinane epoxide | 1686-14-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-α-pinane epoxide
• 英文别名: trans-2,3-Epoxy-pinan；(2S,4R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane
• CAS: 1686-14-2；14575-92-9；19894-99-6；32162-27-9；38301-46-1；94063-22-6；95044-43-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: NQFUSWIGRKFAHK-VUMZSGCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• RTECS号：
  TK4565000
• 海关编码：
  2932999099
• 危险品运输编号：
  UN 2810
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P210,P261,P271,P280,P304+P340+P311,P370+P378,P403+P233,P405,P501
• 危险性描述：
  H227,H331

反应信息

• 作为反应物：
  描述：

  (+/-)-α-pinane epoxide 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以45%的产率得到(1R,5S)-5-(2-羟基-2-丙基)-2-甲基-2-环己烯-1-醇
  参考文献：
  名称：

  Stereocontrolled regiospecificity of the water loss fromtrans-sobrerol radical cation upon electron ionization

  摘要：

  AbstractWater loss from frans‐sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occurring by a stereocontrolled H‐transfer from C(5) position in a rate‐determining step process, as proved by 18O and deuterium labelling. Monomethyl ethers behave accordingly. Ionic structures of the water‐loss product or products are investigated by metastable ion and collision activation mass‐analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to fralts‐sobrerol in condensed phase, i.e. α‐pinane epoxide, cis‐sobrerol and pinol. A substantial conversion of cis‐sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.

  DOI：

  10.1002/oms.1210220809
• 作为产物：
  描述：

  Pinene 在 Mn(N-(4-carboxybenzyl)iminodiacetic acid(-2H))(H₂O) 、 ammonium acetate 、 双氧水 作用下， 以 甲醇 、 丙酮 为溶剂， 以26.2%的产率得到(+/-)-α-pinane epoxide
  参考文献：
  名称：

  Synthesis, Characterization, Magnetic and Catalytic Properties of a Ladder‐Shaped Mn ^II Coordination Polymer

  摘要：

  Abstract[Mn(LH)(H2O)]n {1, where LH2– is the dianion of N‐(4‐carboxybenzyl)iminodiacetic acid} has been synthesized and its crystal structure has been determined. The crystal of 1 is built from 1D polymeric ladder‐shaped chains that extend to a 3D supramolecular architecture through H‐bonds. The compound was characterized with spectroscopic and physicochemical techniques. Variable‐temperature magnetic data suggest that there are weak antiferromagnetic interactions. Compound 1 has been evaluated as a heterogeneous oxidation catalyst. It catalyzes alkene epoxidation selectively in relatively high yields.

  DOI：

  10.1002/ejic.201402419

文献信息

• Photooxygenation of olefins in the presence of titanium(IV) catalyst. A convienient "one-pot" synthesis of epoxy alcohols.
  作者：Waldemar Adam、Martin Braun、Axel Griesbeck、Vittorio Lucchini、Eugen Staab、Bernd Will

  DOI：10.1021/ja00183a032

  日期：1989.1
• BANEI, STEFANO;MONTANARI, FERNANDO;PENSO, MICHELE;SOSNOVSKIKH, VEICHESLAV+, GAZZ. CHIM. ITAL., 117,(1987) N 11, 689-693
  作者：BANEI, STEFANO、MONTANARI, FERNANDO、PENSO, MICHELE、SOSNOVSKIKH, VEICHESLAV+

  DOI：——

  日期：——
• Synthesis, Characterization, Magnetic and Catalytic Properties of a Ladder‐Shaped Mn ^II Coordination Polymer
  作者：Smaragda Lymperopoulou、Maria Papastergiou、Maria Louloudi、Catherine P. Raptopoulou、Vassilis Psycharis、Constantinos J. Milios、John C. Plakatouras

  DOI：10.1002/ejic.201402419

  日期：2014.8

  Abstract[Mn(LH)(H2O)]n 1, where LH2– is the dianion of N‐(4‐carboxybenzyl)iminodiacetic acid} has been synthesized and its crystal structure has been determined. The crystal of 1 is built from 1D polymeric ladder‐shaped chains that extend to a 3D supramolecular architecture through H‐bonds. The compound was characterized with spectroscopic and physicochemical techniques. Variable‐temperature magnetic data suggest that there are weak antiferromagnetic interactions. Compound 1 has been evaluated as a heterogeneous oxidation catalyst. It catalyzes alkene epoxidation selectively in relatively high yields.
• Stereocontrolled regiospecificity of the water loss fromtrans-sobrerol radical cation upon electron ionization
  作者：Antonio Selva、Francesco Ferrario、Paolo Ventura、Renato Pellegata

  DOI：10.1002/oms.1210220809

  日期：1987.8

  AbstractWater loss from frans‐sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occurring by a stereocontrolled H‐transfer from C(5) position in a rate‐determining step process, as proved by 18O and deuterium labelling. Monomethyl ethers behave accordingly. Ionic structures of the water‐loss product or products are investigated by metastable ion and collision activation mass‐analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to fralts‐sobrerol in condensed phase, i.e. α‐pinane epoxide, cis‐sobrerol and pinol. A substantial conversion of cis‐sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.