(3RS,4SR)-3-methyloctan-1,4-diol | 87434-02-4

• 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: (3RS,4SR)-3-methyloctan-1,4-diol
• 英文别名: (3S,4R)-3-methyloctane-1,4-diol
• CAS: 87434-02-4
• 化学式: C₉H₂₀O₂
• 分子量: 160.257
• InChiKey: SXZWQCXQDXILPM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3RS,4SR)-3-methyloctan-1,4-diol 以60%的产率得到
  参考文献：
  名称：

  MORET, E.;SCHLOSSER, M., TETRAHEDRON LETT., 1984, 25, N 40, 4491-4494

  摘要：

  DOI：
• 作为产物：
  描述：

  ((1S,2R)-2-Butyl-cyclopropyl)-acetic acid methyl ester 在 lithium aluminium tetrahydride 、 mercury(II) trifluoroacetate 、 potassium bromide 作用下， 生成 (3RS,4SR)-3-methyloctan-1,4-diol
  参考文献：
  名称：

  汞 (II) 介导的环丙烷打开。邻近内部亲核试剂对立体选择性和区域选择性的影响

  摘要：

  Etude des Effects de Moities acide Carboxylique etester internes sur les regio-et立体选择性内在性 au clivage induit par le le mercure(II) de cyclopropanes nonactives。Bien que les cyclisations Fournissent classiquement des lactones avec une forte 立体选择性，des pertes surprenantes de selectivite sontaccidentnellement 观察

  DOI：

  10.1021/ja00361a024

文献信息

• Precursors to oak lactone. Part 2: Synthesis, separation and cleavage of several β-d-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid
  作者：Kerry L Wilkinson、Gordon M Elsey、Rolf H Prager、Takashi Tanaka、Mark A Sefton

  DOI：10.1016/j.tet.2004.05.070

  日期：2004.7

  The beta-D-glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared. The (3S,4S) and (3R,4R) species were prepared from cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (cis-oak lactone) by a process involving ring-opening with base and protection of the carboxyl function as its benzyl ester. The glucose unit was introduced by a modified Koenigs-Knorr procedure. A different strategy was necessary for synthesis of the (3S,4R) and (3R,4S) compounds. This was based on the reductive ring-opening of trans-oak lactone and subsequent protection of the primary alcohol as its t-butyldiphenylsilyl ether. Separation of the individual glucosides was effected by preparative thin layer chromatography. Those corresponding to the nature-identical isomers of oak lactone have been shown to produce oak lactone under both acidic hydrolysis and pyrolysis conditions. The galloyl-beta-D-glucoside of the cis-species, obtained as a natural isolate from the wood of Platycarya strobilacea, was also found to produce cis-oak lactone upon both acid hydrolysis and pyrolysis. Both the nature-identical (4S,5S) cis-oak lactone and its non-natural (4R,5R) enantiomer have been prepared from their corresponding glycosides and their aroma thresholds in white wine were determined to be 23 and 82 mug/L (ppb) respectively. The aroma threshold of the nature-identical isomer in a red wine was 46 mug/L. (C) 2004 Elsevier Ltd. All rights reserved.
• COLLUM, D. B.;MOHAMADI, F.;HALLOCK, J. S., J. AMER. CHEM. SOC., 1983, 105, N 23, 6882-6889
  作者：COLLUM, D. B.、MOHAMADI, F.、HALLOCK, J. S.

  DOI：——

  日期：——