(S,S)-1-methylcyclohexene oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (S,S)-1-methylcyclohexene oxide
• 英文别名: (1s,2s)-1-Methyl-1,2-epoxycyclohexane；(1S,6S)-1-methyl-7-oxabicyclo[4.1.0]heptane
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: FIEKVYPYFQSFTP-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  3-甲基-1-环己烯 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， 反应 6.0h， 以81.6%的产率得到(S,S)-1-methylcyclohexene oxide
  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

• An Efficient Catalytic Asymmetric Epoxidation Method
  作者：Zhi-Xian Wang、Yong Tu、Michael Frohn、Jian-Rong Zhang、Yian Shi

  DOI：10.1021/ja972272g

  日期：1997.11.1

  This article describes a highly effective catalytic asymmetric epoxidation method for olefins using potassium peroxomonosulfate (Oxone, Dupont) as oxidant and a fructose-derived ketone (1) as catalyst. High enantioselectivies have been obtained for trans-disubstituted and trisubstituted olefins which can bear functional groups such as tributylsilyl ether, acetal, chloride, and ester. The enantiomeric

  本文描述了一种使用过一硫酸钾（Oxone，Dupont）作为氧化剂和果糖衍生的酮 (1) 作为催化剂的烯烃高效催化不对称环氧化方法。对于可以带有三丁基甲硅烷基醚、缩醛、氯化物和酯等官能团的反式二取代和三取代烯烃，已经获得了高对映选择性。顺式烯烃和末端烯烃的对映体过量还不高。目前的环氧化反应表明，提高 pH 值后催化剂效率显着提高。机理研究表明，环氧化主要通过螺过渡态进行，这为预测反应的立体化学结果提供了模型。平面过渡态可能是主要的竞争途径。
• 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.