(R/S)-[2-(2)H]Octan-2-ol | 16428-56-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R/S)-[2-(2)H]Octan-2-ol
• 英文别名: 2-deuterio-2-octanol；2-deuteriooctan-2-ol；2-Deuteriooctan-2-ol
• CAS: 16428-56-1
• 化学式: C₈H₁₈O
• 分子量: 131.222
• InChiKey: SJWFXCIHNDVPSH-BNEYPBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R/S)-[2-(2)H]Octan-2-ol 在 4,7-di-(NaSO₃Ph)-[1.10]phenanthroline-Pd(OAc)2 sodium acetate 作用下， 99.84 ℃ 、3.0 MPa 条件下， 生成 仲辛酮
  参考文献：
  名称：

  Catalytic Conversions in Water. Part 21: Mechanistic Investigations on the Palladium-Catalysed Aerobic Oxidation of Alcohols in Water†

  摘要：

  Water-soluble complexes of palladium(II) with phenanthroline-derivatives are stable, recyclable catalysts for the selective aerobic oxidation of a wide range of alcohols to aldehydes, ketones, and carboxylic acids in a biphasic liquid-liquid system. The active catalyst is a dihydroxy-bridged palladium dimer. Kinetics of the reaction, ligand and anion effects are discussed.

  DOI：

  10.1002/1615-4169(200206)344:3/4<355::aid-adsc355>3.0.co;2-s
• 作为产物：
  描述：

  仲辛酮 在 硼氘化钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到(R/S)-[2-(2)H]Octan-2-ol
  参考文献：
  名称：

  Stereoselective oxidation and reduction by immobilized Geotrichum candidum in an organic solvent

  摘要：

  将真菌地霉菌（Geotrichum candidum）的细胞固定在水吸收性聚合物上，并用于在有机溶剂中以环己酮、环戊醇或烷-2-醇作为添加剂进行立体选择性氧化和还原反应。通过立体选择性氧化外消旋1-芳基乙醇，获得了对映体纯的（R）-1-芳基乙醇，而通过对相应的酮进行还原，获得了对映体纯的（S）-1-芳基乙醇，这与自由细胞在水中的还原反应不同，后者仅产生低ee值的（R）-或（S）-1-芳基乙醇。通过测量细胞固定在聚合物周围的有机相和水分相中底物和产物的分布，研究了反应机制。使用氘代化合物来确定添加剂的作用。

  DOI：

  10.1039/a900936a

文献信息

• Stereoselective oxidation and reduction by immobilized Geotrichum candidum in an organic solvent
  作者：Kaoru Nakamura、Yuko Inoue、Tomoko Matsuda、Ibuki Misawa

  DOI：10.1039/a900936a

  日期：——

  Cells of the fungus, Geotrichum candidum, were immobilized on a water-absorbing polymer and used for stereoselective oxidation and reduction in an organic solvent using cyclohexanone, cyclopentanol or alkan-2-ols as additive. Enantiomerically pure (R)-1-arylethanols were obtained by the stereoselective oxidation of racemic 1-arylethanols, whereas enantiomerically pure (S)-1-arylethanols were obtained by the reduction of the corresponding ketones, in contrast to reduction in water by the free cells in which (R)- or (S)-1-arylethanols were produced in low ee.The reaction mechanism was investigated by measuring the partition of the substrates and products between the organic phase and aqueous phase in the polymer around which the cells were immobilized. Deuterated compounds were used to determine the role of the additives.

  将真菌地霉菌（Geotrichum candidum）的细胞固定在水吸收性聚合物上，并用于在有机溶剂中以环己酮、环戊醇或烷-2-醇作为添加剂进行立体选择性氧化和还原反应。通过立体选择性氧化外消旋1-芳基乙醇，获得了对映体纯的（R）-1-芳基乙醇，而通过对相应的酮进行还原，获得了对映体纯的（S）-1-芳基乙醇，这与自由细胞在水中的还原反应不同，后者仅产生低ee值的（R）-或（S）-1-芳基乙醇。通过测量细胞固定在聚合物周围的有机相和水分相中底物和产物的分布，研究了反应机制。使用氘代化合物来确定添加剂的作用。
• Enantiomeric Analysis of Homologous Series of Secondary Alcohols by Deuterium NMR Spectroscopy in a Chiral Nematic Liquid Crystal: Influence of Molecular Geometry on Chiral Discrimination
  作者：A. Meddour、D. Atkinson、A. Loewenstein、J. Courtieu

  DOI：10.1002/(sici)1521-3765(19980710)4:7<1142::aid-chem1142>3.0.co;2-q

  日期：1998.7.10

  NMR measurements of the differential ordering effect (DOE) are presented for homologous series of 22 chiral secondary aliphatic alcohols dissolved in a poly-(gamma-benzyl-L-glutamate) (PBLG)/dichloromethane liquid-crystalline solvent. The quadrupolar splittings of the solutes, which were deuterated at their chiral centres, were measured as a function of the PBLG concentration and temperature. The proton dipolar splittings of the dichloromethane in each sample were also measured and used as a reference. The results are analysed qualitatively in terms of the structures of the molecules and their asymmetric (or chiral) characteristics. Emphasis is put on comparative analysis of the chiral discrimination in members of each particular homologous series and on evaluating the Limits of the technique for molecules that have two very similar groups attached to their stereogenic centres.
• Stereochemistry of the Primary Carbon. I. Optically Active n-Butanol-1-d¹
  作者：Andrew Streitwieser

  DOI：10.1021/ja01116a038

  日期：1953.10
• Catalytic Conversions in Water. Part 21: Mechanistic Investigations on the Palladium-Catalysed Aerobic Oxidation of Alcohols in Water†
  作者：Gerd-Jan ten??Brink、Isabel??W.??C.??E. Arends、Roger??A. Sheldon

  DOI：10.1002/1615-4169(200206)344:3/4<355::aid-adsc355>3.0.co;2-s

  日期：2002.6

  Water-soluble complexes of palladium(II) with phenanthroline-derivatives are stable, recyclable catalysts for the selective aerobic oxidation of a wide range of alcohols to aldehydes, ketones, and carboxylic acids in a biphasic liquid-liquid system. The active catalyst is a dihydroxy-bridged palladium dimer. Kinetics of the reaction, ligand and anion effects are discussed.
• Photochemistry of Racemic and Resolved 2-Iodooctane. Effect of Solvent Polarity and Viscosity on the Chemistry
  作者：Fang Gao、David Boyles、Rodney Sullivan、Robert N. Compton、Richard M. Pagni

  DOI：10.1021/jo020472r

  日期：2002.12.1

  resolved 2-iodooctane was examined in cyclopentane, methanol, and 2-methyl-2-propanol, media with differing polarities and viscosities. The photochemistry of racemic 2-iodooctane was also examined in the gas phase. The photochemistry of 2-deuterio- and 1,1,1-trideuterio-2-iodooctane in cyclopentane and methanol was also studied. The photoreactions in cyclopentane, 2-methyl-2-propanol, and the gas phase

  在环戊烷，甲醇和2-甲基-2-丙醇（极性和粘度不同的介质）中检查了外消旋和拆分的2-碘辛烷的光化学性质。还在气相中检查了外消旋2-碘辛烷的光化学。还研究了2-氘-和1,1,1-三碘-2-碘辛烷在环戊烷和甲醇中的光化学性质。在环戊烷，2-甲基-2-丙醇和气相中的光反应仅通过均相反应发生，而在甲醇中，它们主要通过杂化反应（> 53％）发生。通过将旋光性基材的消失与旋光性的损失F进行比较，确定了三种溶剂中最初形成的自由基对（RP）或离子对（IP）的分数。因为F包含了RP或IP中的伙伴逃逸到大部分溶剂中以及RP或IP中的反应产生了底物以外的产物，所以F与溶剂粘度之间没有相关性。F值对于评估圆偏振光在相同介质中的2-碘辛烷的光化学价值将很有价值。