(2S,3S)-4-cyclohexyl-2,3-epoxy-1-butanol | 176487-03-9

• 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: (2S,3S)-4-cyclohexyl-2,3-epoxy-1-butanol
• 英文别名: (2S,3S)-4-cyclohexyl-2,3-epoxybutan-1-ol；[(2S,3S)-3-(cyclohexylmethyl)oxiran-2-yl]methanol
• CAS: 176487-03-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: ODBGWHBDZBWNMM-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-4-cyclohexyl-2,3-epoxy-1-butanol 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以71.5%的产率得到(2R,3S)-3-(cyclohexylmethyl)oxirane-2-carboxylic acid
  参考文献：
  名称：

  Stereoselective Preparation of Syn α-Hydroxy-β-amino Ester Units via Regioselective Opening of α,β-Epoxy Esters:  Enantioselective Synthesis of Taxol C-13 Side Chain and Cyclohexylnorstatine

  摘要：

  DOI：

  10.1021/jo951441h
• 作为产物：
  描述：

  (E)-4-cyclohexyl-2-buten-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(2S,3S)-4-cyclohexyl-2,3-epoxy-1-butanol
  参考文献：
  名称：

  Stereoselective Preparation of Syn α-Hydroxy-β-amino Ester Units via Regioselective Opening of α,β-Epoxy Esters:  Enantioselective Synthesis of Taxol C-13 Side Chain and Cyclohexylnorstatine

  摘要：

  DOI：

  10.1021/jo951441h

文献信息

• Prompt Determination of Absolute Configuration for Epoxy Alcohols via Exciton Chirality Protocol
  作者：Xiaoyong Li、Babak Borhan

  DOI：10.1021/ja805058t

  日期：2008.12.3

  A microscale protocol for determination of absolute configurations of 2,3-epoxy alcohols is described. 2,3-Disubstituted (cis and trans), 2,2-disubstituted, 2,2,3-trisubstituted, and 2,3,3-trisubstituted epoxy alcohols rendered prominent ECCD signals upon complexing with a Lewis acidic porphyrin tweezer and consequently provide straightforward assignment of chirality for epoxy alcohols. This method

  描述了用于确定 2,3-环氧醇绝对配置的微型协议。2,3-二取代（顺式和反式）、2,2-二取代、2,2,3-三取代和 2,3,3-三取代环氧醇在与路易斯酸性卟啉镊子复合后呈现显着的 ECCD 信号，从而提供环氧醇手性的直接分配。事实证明，对于上面列出的分子类别，该方法快速、简单、灵敏且可靠。
• A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds
  作者：Antonella De Mico、Roberto Margarita、Luca Parlanti、Andrea Vescovi、Giovanni Piancatelli

  DOI：10.1021/jo971046m

  日期：1997.10.1

  Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.
• A Catalytic Asymmetric Synthesis of Cyclohexylnorstatine
  作者：Mireia Pastó、Patrícia Castejón、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo960351p

  日期：1996.1.1