2-methyl-2,3-epoxynonane | 65395-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-methyl-2,3-epoxynonane
• 英文别名: 3-hexyl-2,2-dimethyl-oxirane；(+/-)-2-Methyl-2,3-epoxynonane；3-hexyl-2,2-dimethyloxirane
• CAS: 65395-52-0
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: KPFYLNLVYOGVSB-UHFFFAOYSA-N

物化性质

• 沸点：
  182.8±8.0 °C(Predicted)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  2-methyl-2,3-epoxynonane 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-甲基壬烷-2,3-二醇
  参考文献：
  名称：

  Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes

  摘要：

  Asymmetric biohydrolysis of trialkyl oxiranes (+/-)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols Ib 3b in Lip to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence vas investigated by O-18-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00256-7
• 作为产物：
  描述：

  正庚基三苯基溴化磷 在 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 2-methyl-2,3-epoxynonane
  参考文献：
  名称：

  Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes

  摘要：

  Asymmetric biohydrolysis of trialkyl oxiranes (+/-)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols Ib 3b in Lip to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence vas investigated by O-18-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00256-7

文献信息

• ISOMERIZATION OF OXIRANES TO ALLYLIC ALCOHOLS WITH DIALKYLBORYL TRIFLUOROMETHANESULFONATES
  作者：Tan Inoue、Tadafumi Uchimaru、Teruaki Mukaiyama

  DOI：10.1246/cl.1977.1215

  日期：1977.10.5

  Isomerization of oxiranes to allylic alcohols by treatment with dialkylboryl trifluoromethanesulfonates and tertiary amines is described. Several reactions proceed in regioselective manner.

  介绍了通过二烷基三氟甲磺酸苄基酯和叔胺的处理将环氧乙烷异构化为烯丙基醇的过程。一些反应以区域选择性方式进行。
• Alkylation of 2-Substituted (6-Methyl-2-pyridyl)methyllithium Species with Epoxides
  作者：James R. Vyvyan、Rebecca C. Brown、Brian P. Woods

  DOI：10.1021/jo802267n

  日期：2009.2.6

  Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted (6-methyl-2-pyridyl)methyllithium derivatives. The trisubstituted epoxide gave low yields of adducts with all (2-pyridyl)methyllithium species studied. These results are discussed in the context of a proposed synthesis of cananodine.
• Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes
  作者：Andreas Steinreiber、Sandra F. Mayer、Robert Saf、Kurt Faber

  DOI：10.1016/s0957-4166(01)00256-7

  日期：2001.6

  Asymmetric biohydrolysis of trialkyl oxiranes (+/-)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols Ib 3b in Lip to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence vas investigated by O-18-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.