(1R,3S,5S)-exo-1-3-dimethyl-2,9-dioxabicyclo<3.3.1.>nonane | 76740-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,5S)-exo-1-3-dimethyl-2,9-dioxabicyclo<3.3.1.>nonane
• 英文别名: (-)-(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；(1R,3S,5S)-(-)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；exo-(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；(1S,3R,5R)-1,3-dimethyl-2,9-dioxabicyclo<3.3.1>nonane；(1R,3S,5S)-1,3-Dimethyl-2,9-dioxabicyclo<3.3.1>nonan；(1R,3S,5S)-exo-1-3-dimethyl-2,9-dioxabicyclo[3.3.1.]nonane；(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane
• CAS: 76740-36-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: HNESZEUAUXADTQ-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4,6-Tridesoxy-5-O-tetrahydropyranyl-L-threo-hexose-trimethylendithioacetal 在 镍 重铬酸吡啶 、 正丁基锂 、 5A molecular sieve 、 硫酸 、 氢气 、 对甲苯磺酸 、 copper(II) sulfate 、 2,2-二甲氧基丙烷 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (1R,3S,5S)-exo-1-3-dimethyl-2,9-dioxabicyclo<3.3.1.>nonane
  参考文献：
  名称：

  Redlich, Hartmut; Schneider, Bernd; Hoffmann, Reinhard W., Liebigs Annalen der Chemie, 1983, # 3, p. 393 - 411

  摘要：

  DOI：

文献信息

• Facile Construction of Optically Active 1,3-Diols. Synthesis of (2<i>S</i>,4<i>R</i>)-7-Octene-2,4-diol and<i>endo</i>-(1<i>S</i>,3<i>S</i>,5<i>R</i>)- and<i>exo</i>-(1<i>R</i>,3<i>S</i>,5<i>S</i>)-1,3-Dimethyl-2,9-dioxabicyclo[3.3.1]nonane
  作者：Hidenori Chikashita、Eiji Kittaka、Yasunori Kimura、Kazuyoshi Itoh

  DOI：10.1246/bcsj.62.833

  日期：1989.3

  A short and stereoselective asymmetric synthesis of (2S,4R)-7-octene-2,4-diol (a key intermediate in the Bartlett synthesis of nonactic acid) and two stereoisomers of a biologically active substance isolated from Norway spruce infested by ambrosia beetle, endo-(1S,3S,5R)- and exo-(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo-[3.3.1]nonane, was effectively accomplished in three and four reaction steps, respectively

  (2S,4R)-7-octene-2,4-diol（非乳酸合成 Bartlett 中的关键中间体）和两种生物活性物质的立体异构体的立体选择性不对称合成,内-(1S,3S,5R)-和外-(1R,3S,5S)-1,3-二甲基-2,9-二氧杂双环-[3.3.1]壬烷，在三个和四个反应步骤中有效完成分别通过面包酵母不对称还原从容易获得的 (S)-1-(1,3-dithian-2-yl)-2-丙醇开始。主要策略是基于通过（S）-1-（1,3-二噻烷-2-基）-2-丙醇的二价阴离子与烷基卤化物的烷基化，轻松构建光学活性β-羟基酮，然后是它们的立体选择性还原。
• Synthesis of isomeric 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonanes and 1’-hydroxybrevicomin from ethyl 5-oxohexenoate ethyleneacetal through cyclopropanation of an ester group followed by oxidative opening of the three-membered ring
  作者：D. A. Astashko、O. G. Kulinkovich、V. I. Tyvorskii

  DOI：10.1134/s1070428006050125

  日期：2006.5

  Syntheses were performed of (+/-)-endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane and (+/-)-1'-hydroxyexo-brevicomin constituting racemic forms of the secretion components of pine weever (Hylobius abietis) and bark beetle of upland pines (Dendroctonus ponderosae) through cyclopropanation of the ester group of an available ethyl 5-oxohexanoate ethyleneacetal with the subsequent oxidative opening of the three-membered ring in the compound obtained.
• Offenkettige zuckerdithioacetale als bausteine in der naturstoffsynthese III synthese der vier isomeren 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane aus -glucose
  作者：Hartmut Redlich、Bernd Schneider、Wittko Francke

  DOI：10.1016/0040-4039(80)88024-5

  日期：1980.1
• Page, Philip C. Bulman; Rayner, Christopher M.; Sutherland, Ian O., Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2403 - 2408
  作者：Page, Philip C. Bulman、Rayner, Christopher M.、Sutherland, Ian O.

  DOI：——

  日期：——
• Use of biological systems for the preparation of chiral molecules. 6. Preparation of stereoisomeric 2,4-diols: synthesis and conformational study of bicyclo derivatives, isomeric components of a pheromone of Trypodendron lineatum
  作者：G. Dauphin、A. Fauve、H. Veschambre

  DOI：10.1021/jo00270a040

  日期：1989.4