(R,R)-2-acetoxycyclooctan-1-ol | 133442-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R,R)-2-acetoxycyclooctan-1-ol
• 英文别名: 1,2-Cyclooctanediol, 1-acetate, (1R,2R)-；[(1R,2R)-2-hydroxycyclooctyl] acetate
• CAS: 133442-56-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: RJUXQJLUPNFXAC-NXEZZACHSA-N

物化性质

• 沸点：
  263.7±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (R,R)-1,2-diacetoxycyclooctane 生成 (R,R)-2-acetoxycyclooctan-1-ol
  参考文献：
  名称：

  SEEMAYER, R.;SCHNEIDER, M. P., J. CHEM. SOC. CHEM. COMMUN.,(1991) N, C. 49-50

  摘要：

  DOI：

文献信息

• Kinetic resolution of trans-cycloalkane-1,2-diols via Steglich esterification
  作者：Radim Hrdina、Christian E. Müller、Peter R. Schreiner

  DOI：10.1039/c001075h

  日期：——

  We describe the efficient and highly enantioselective kinetic resolution of trans-cycloalkane-1,2-diols utilizing an enantioselective Steglich reaction with a variety of carboxylic acids that form the corresponding anhydrides in situ.

  我们描述了利用具有多种羧酸（这些羧酸在位形成相应酸酐）的手性Steglich反应，对反式环烷-1,2-二醇进行高效和高对映选择性的动力学拆分。
• Enantiomerically enriched trans-diols from alkenes in one pot: a multicatalyst approach
  作者：Radim Hrdina、Christian E. Müller、Raffael C. Wende、Lukas Wanka、Peter R. Schreiner

  DOI：10.1039/c2cc17435a

  日期：——

  Multicatalysts consisting of non-natural oligopeptides with distinctly different catalytic moieties create molecular complexity in a multistep one-pot sequence starting from simple alkenes yielding highly enantiomerically enriched trans-diols.

  由非天然寡肽组成的多催化剂，具有明显不同的催化基团，在从简单的烯烃出发的多步一锅反应中创造了分子复杂性，最终生成具有高度对映体富集的反式二醇。
• Enzymatic preparation of optically pure trans-1,2-cycloalkanediols
  作者：R. Seemayer、M. P. Schneider

  DOI：10.1039/c39910000049

  日期：——

  trans-1,2-Cycloalkanediols (R,R)-1–4 and (S,S)-1–3 of high optical purities are prepared by enzymatic hydrolysis and esterification catalysed by a lipase from Pseudomonas sp. (SAM II).

  高光学纯度的反式-1,2-环烷二醇(R,R)-1–4和(S,S)-1–3是通过由假单胞菌(SAM II)催化的酶解和酯化反应制备的。
• Enantioselective Kinetic Resolution of<i>trans</i>-Cycloalkane-1,2-diols
  作者：Christian E. Müller、Lukas Wanka、Kevin Jewell、Peter R. Schreiner

  DOI：10.1002/anie.200800641

  日期：2008.8.4
• Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification
  作者：Christine Hofmann、Jan M. Schümann、Peter R. Schreiner

  DOI：10.1021/jo502670p

  日期：2015.2.6

  We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N'-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.