(2R)-(-)-2-hydroxyhexan-4-one | 116531-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-(-)-2-hydroxyhexan-4-one
• 英文别名: (5R)-5-hydroxyhexan-3-one
• CAS: 116531-35-2
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: XHYXKWWFNRBCGE-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4-己二酮 在 葡萄糖 作用下， 以 水 为溶剂， 反应 10.0h， 以100%的产率得到(2R)-(-)-2-hydroxyhexan-4-one
  参考文献：
  名称：

  Use of biological systems for the synthesis of chiral molecules. 5. Microbiological reduction of acyclic .beta.-diketones

  摘要：

  DOI：

  10.1021/jo00257a004

文献信息

• Metal-Free Catalytic Boration at the β-Position of α,β-Unsaturated Compounds: A Challenging Asymmetric Induction
  作者：Amadeu Bonet、Henrik Gulyás、Elena Fernández

  DOI：10.1002/anie.201001198

  日期：——

  Enantiomerically enriched secondary organoboronates containing β‐carbonyl functional groups have been prepared using an unprecedented organocatalytic system (see scheme). The use of chiral tertiary phosphorus compounds induced ee values of up to 95 % in the absence of transition metals.

  使用史无前例的有机催化体系制备了含有β-羰基官能团的对映体富集的仲有机硼酸酯（参见方案）。在不存在过渡金属的情况下，使用手性叔磷化合物可导致ee值高达95％。
• Reductive biotransformation of carbonyl compounds—application of fungus, Geotrichum sp. G38 in organic synthesis
  作者：Gu Jian-Xin、Li Zu-Yi、Lin Guo-Qiang

  DOI：10.1016/s0040-4020(01)87947-3

  日期：1993.6

  The microbial transformation of 2- and 3-oxo esters and diketones with Geotrichum sp. G38 and its application to the syntheses of the key intermediates of several bioactive compounds such as (R)-denopamine 8, (R)-fluoxetine 11 and (2S, 3R)-sitophilate 14 were described.

  Geotrichum sp对2-和3-氧代酯和二酮的微生物转化。描述了G38及其在几种生物活性化合物如（R）-地巴胺8，（R）-氟西汀11和（2S，3R）-sitophilate 14的关键中间体的合成中的应用。
• Ohta, Hiromichi; Ozaki, Kazuhiko; Tsuchihashi, Gen-ichi, Agricultural and Biological Chemistry, 1986, vol. 50, # 10, p. 2499 - 2502
  作者：Ohta, Hiromichi、Ozaki, Kazuhiko、Tsuchihashi, Gen-ichi

  DOI：——

  日期：——
• Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl^-]. Stereochemistry of the Wacker Reaction
  作者：Othman Hamed、Patrick M. Henry、Charles Thompson

  DOI：10.1021/jo9906274

  日期：1999.10.1

  At high [Cl-] (> 2.0 M), PdCl42- catalyzes the exchange of chiral allylic alcohols with hydroxy, methoxy, and phenyl to give chiral allyl-substituted olefins. With unsymmetrical olefins, isomerization occurs along with exchange. The hydroxyl exchange occurs in aqueous solution while the other exchanges are carried out in methanol solution. At low [Cl-] (0.1 M) oxidation to the corresponding beta-hydroxy-, methoxy-, and phenyl-substituted carbonyl compounds occurred. The absolute configurations of the oxidation and exchange products should be the same if the same mode of addition to the Pd(II)-pi-complex is operative. The absolute configurations of the oxidation and exchange products for the phenylation reaction were the same, while for hydroxy and methoxy they were different. This result indicates methanol and water must have different stereochemistries of addition at high and low [Cl-]. Thus, previous studies showing anti hydroxypalladation at high [Cl-] are not valid indicators of the stereochemistry at low [Cl-]. If anti addition occurs at high [Cl-], the addition must be syn at low [Cl-].
• FAUVE, ANNIE;VESCHAMBRE, HENRI, J. ORG. CHEM., 53,(1988) N2, C. 5215-5219
  作者：FAUVE, ANNIE、VESCHAMBRE, HENRI

  DOI：——

  日期：——