(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：——
• Mercury(II)-mediated opening of cyclopropanes. Effects of proximate internal nucleophiles on stereo- and regioselectivity
  作者：David B. Collum、Fariborz Mohamadi、John S. Hallock

  DOI：10.1021/ja00361a024

  日期：1983.11

  Etude des effets de moities acide carboxylique et ester internes sur les regio- et stereoselectivites inherentes au clivage induit par le mercure(II) de cyclopropanes non actives. Bien que les cyclisations fournissent classiquement des lactones avec une forte stereoselectivite, des pertes surprenantes de selectivite sont occasionnellement observees

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

  DOI：——

  日期：——