(1S,2R)-1-acetoxy-2-hydroxycyclohexane | 119180-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-1-acetoxy-2-hydroxycyclohexane
• 英文别名: cis-1-acetyl-2-cyclohexanol；cis-Cyclohexan-1,2-diol-monoacetat；cis-1-Acetoxy-2-hydroxycyclohexan；cis-2-Acetoxy-1-cyclohexanol；cis-2-Acetoxycyclohexanol；cis-2-Hydroxycyclohexylacetat；[(1S,2R)-2-hydroxycyclohexyl] acetate
• CAS: 119180-48-2
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: GCPZLJNKHNJVGF-SFYZADRCSA-N

物化性质

• 沸点：
  222.2±23.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2-diacetoxy-cyclohexane 以35%的产率得到
  参考文献：
  名称：

  XIE, ZHUO-FENG;NAKAMURA, IZUMI;SUEMUNE, HIROSHI;SAKAI, KIYOSHI, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 14, C. 966-967

  摘要：

  DOI：

文献信息

• A Multicatalyst System for the One‐Pot Desymmetrization/Oxidation of <i>meso</i> ‐1,2‐Alkane Diols
  作者：Christian E. Müller、Radim Hrdina、Raffael C. Wende、Peter R. Schreiner

  DOI：10.1002/chem.201100498

  日期：2011.5.27

  Two is better than one: We demonstrate the viability of an organocatalytic reaction sequence along a short peptide backbone that carries two independent catalytic functionalities, which allow the rapid, one‐pot acylative desymmetrization and oxidation of meso‐alkane‐1,2‐diols to the corresponding acetylated acetoins with good yields and enantioselectivities (see scheme).

  两个优于一个：我们证明的有机催化反应序列的沿着承载两个独立的催化功能，其允许快速，一锅acylative desymmetrization和氧化的短肽骨架的生存能力内消旋-烷烃-1,2-二醇来具有良好产率和对映选择性的相应乙酰化乙酰丙酮（参见方案）。
• One-Pot Desymmetrization of<i>meso</i>-1,2-Hydrocarbon Diols through Acylation and Oxidation
  作者：Christian E. Müller、Daniela Zell、Peter R. Schreiner

  DOI：10.1002/chem.200901711

  日期：2009.9.28

  Avoid racemization! Short lipophilic oligopeptides utilizing nucleophilic N‐π‐methyl histidine residues catalyze the desymmetrization of meso‐1,2‐diols with enantiomeric ratios of up to 94:6. Direct one‐pot oxidation, which avoids the well‐known racemization of the monoacylated product, directly leads to α‐acetoxy ketones with enantiomeric ratios of up to 97:3 and 97 % yield.

  避免消旋！利用亲核性N -π-甲基组氨酸残基的短亲脂性寡肽催化对映体比率高达94：6的内消旋1,2-二醇脱对称化。直接一锅氧化避免了单酰化产物的众所周知的外消旋化作用，直接导致对映体比率高达97：3且产率为97％的α-乙酰氧基酮。
• Asymmetric Hydrolyses of 1,2-Diacetoxycyclohexanes by the Cultured Suspension Cells of<i>Marchantia polymorpha</i>
  作者：Shisei Gotoh、Masahiro Aoki、Tomoko Iwaeda、Shunsuke Izumi、Toshifumi Hirata

  DOI：10.1246/cl.1994.1519

  日期：1994.8

  The enantioselectivity in the hydrolyses of cis- and trans-1,2-diacetoxycyclohexanes by the cultured suspension cells of Marchantia polymorpha was very high. The acetoxyl groups at the stereogenic center of (R)-configuration were preferentially hydrolyzed.

  马钱子悬浮培养细胞水解顺式和反式-1,2-二乙酰氧基环己烷的对映选择性非常高。位于(R)-构型立体中心的乙酰氧基被优先水解。
• An insight into the enantioselective hydrolyses of cyclic acetates catalysed by Pseudomonas fluorescens lipase
  作者：Zhuo-Feng Xie、Izumi Nakamura、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1039/c39880000966

  日期：——

  Hydrolysis of racemic acetates with Pseudomonas fluorescens lipase (PFL) afforded optically active alcohols with the R-configuration, independent of ring size; a three-site model for PFL-catalysed hydrolysis is proposed.

  用荧光假单胞菌脂肪酶（PFL）水解外消旋乙酸酯，得到具有R-构型的旋光性醇，与环的大小无关。提出了PFL催化水解的三点模型。
• Lipase-catalyzed enantioselective acylation of alcohols: a predictive active site model for lipase YS to identify which enantiomer of an alcohol reacts faster in this acylation
  作者：Koichiro Naemura、Ritsuko Fukuda、Masaki Murata、Masayoshi Konishi、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(95)00316-h

  日期：1995.9

  Primary alcohols having a hydroxymethyl group at an S stereogemic center and secondary alcohols with an R configuration are preferentially acylated to give the corresponding acetates by lipase YS (from Pseudomonas fluorescens)-catalyzed acylation using isopropenyl acetate as the acylating agent in diisopropyl ether. On the basis of enantiomer selectivities observed, a predictive active site model for lipase YS is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation.