cis-1-acetoxycyclohexane-2-ol | 86703-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-acetoxycyclohexane-2-ol
• 英文别名: cis-2-hydroxy acetoxycyclohexane；cis-1,2-cyclohexanediol monoacetate；(+/-)-cis-1-acetoxy-2-hydroxycyclohexane；[(1R,2S)-2-hydroxycyclohexyl] acetate
• CAS: 86703-56-2
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: GCPZLJNKHNJVGF-JGVFFNPUSA-N

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

• 作为反应物：
  描述：

  cis-1-acetoxycyclohexane-2-ol 在 吡啶 、 乙酸酐 、 溶剂黄146 作用下， 生成 trans-1,2-cyclohexanediol diacetate
  参考文献：
  名称：

  The Role of Neighboring Groups in Replacement Reactions. XI. Some Reactivities Involving Neighboring Groups¹

  摘要：

  DOI：

  10.1021/ja01182a112
• 作为产物：
  描述：

  cis-1,2-diacetoxycyclohexane 在 硫酸 、 溶剂黄146 作用下， 生成 cis-1-acetoxycyclohexane-2-ol
  参考文献：
  名称：

  The Role of Neighboring Groups in Replacement Reactions. I. Retention of Configuration in the Reaction of Some Dihalides and Acetoxyhalides with Silver Acetate¹

  摘要：

  DOI：

  10.1021/ja01264a020

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）。
• Reactions of thallium(I) carboxylates and iodine with alkenes
  作者：Richard C. Cambie、Rodney C. Hayward、John L. Roberts、Peter S. Rutledge

  DOI：10.1039/p19740001858

  日期：——

  Treatment of an alkene with a thallium(I) carboxylate and iodine gives the corresponding vic-iodocarboxylate in high yield. The reactions are regiospecific and in conjunction with solvolysis of the products, offer an alternative to the Prévost reaction. Differences in the behaviour of thallium(I) carboxylates and silver carboxylates towards alkenes in the presence of iodine are discussed.

  用铊（烯烃的治疗我）羧酸酯和碘给出了相应的VIC以高收率-iodocarboxylate。该反应是区域特异性的，并与产物的溶剂分解结合，提供了Prévost反应的替代方法。讨论了在碘存在下of （I）羧酸盐和羧酸银对烯烃的行为差异。
• Bismuth(<scp>III</scp>) acetate: a cheap, efficient, and environmentally acceptable reagent for ‘wet’ and ‘dry’ prevost reactions
  作者：Eva M. Campi、Glen B. Deacon、Gavin L. Edwards、Mark D. Fitzroy、Nunzio Giunta、W. Roy Jackson、Robert Trainor

  DOI：10.1039/c39890000407

  日期：——

  cis- and trans-Diol derivatives can be prepared from alkenes by reaction with bismuth(III) acetate in ‘wet’ and ‘dry’ acetic acid respectively.

  顺式和反式二元醇衍生物可以通过与分别在“湿”和“干”乙酸中的乙酸铋（III）反应从烯烃制得。
• Aerobic Oxidation of Alkenes to Esters of Vicinal Diols with a<i>syn</i>-Configuration Catalyzed by I₂and the H₅PV₂Mo₁₀O₄₀Polyoxometalate
  作者：Ronny Neumann、Olena Branytska

  DOI：10.1055/s-2005-917069

  日期：——

  A new method for the synthesis of vicinal diols from alkenes has been developed. Reaction of molecular iodine in the presence of a polyoxometalate as oxidation catalyst under aerobic conditions in acetic acid solvent leads to the oxidative iodoacetoxylation of an alkene, i.e. formation of a 1,2-iodoacetate. Further in situ substitution of the iodide by water yields the 1,2-diol monoacetate with a predominantly

  开发了一种从烯烃合成邻二醇的新方法。在作为氧化催化剂的多金属氧酸盐存在下，在有氧条件下，在乙酸溶剂中分子碘的反应导致烯烃的氧化碘乙酰氧基化，即形成1,2-碘乙酸盐。碘化物进一步被水原位取代产生具有主要（约4.5:1）顺式构型的1,2-二醇单乙酸酯。在反应的酸性条件下进一步酯化也会生成顺式二乙酸酯。该方法对于不使用有毒锇催化剂合成顺式邻位二醇可能是有价值的。
• A New Synthesis of<i>cis</i>-Diol from Alkene Using Iodine-Ammonium Cerium(IV) Nitrate
  作者：C. Akira Horiuchi、Gong Dan、Masaki Sakamoto、Kazuhiko Suda、Shigeru Usui、Okihiko Sakamoto、Shinya Kitoh、Satoshi Watanabe、Takamitsu Utsukihara、Sukekatsu Nozaki

  DOI：10.1055/s-2005-916040

  日期：——

  The reaction mixtures of 5α-cholest-2-ene with iodine-ammonium cerium(IV) nitrate [CAN(IV)] were converted with potassium hydroxide in methanol-water to give the more hindered 2β,3β-diol in high yield. Cyclohexene and cycloheptene similarly reacted to the corresponding cis-diols in good yield. It was found that this reaction intermediate proceeds to give trans-iodoacetate via trans-iodonitrate. This new synthetic method provided several advantages over the Prevost reaction.

  5α-胆甾-2-烯与碘化铵硝酸铈(IV)[CAN(IV)]的反应混合物在甲醇-水溶液中用氢氧化钾处理，以高产率得到空间位阻较大的2β,3β-二醇。环己烯和环庚烯也以优良产率生成相应的顺式-二醇。研究发现，该反应中间体通过反式-碘硝酸盐生成反式-碘乙酸盐。这种新的合成方法相比于Prevost反应具有若干优势。