(2S,8S)-(+)-dihydroxynonane | 141667-22-3

• 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: (2S,8S)-(+)-dihydroxynonane
• 英文别名: (S,S)-2,8-Dihydroxynonane；(2S,8S)-nonane-2,8-diol
• CAS: 141667-22-3
• 化学式: C₉H₂₀O₂
• 分子量: 160.257
• InChiKey: TUVOFCSJXRZIOZ-IUCAKERBSA-N

物化性质

• 沸点：
  262.6±8.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：

  (2S,8S)-(+)-dihydroxynonane 在 氢氧化钾 、 copper(l) iodide 、 正丁基锂 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.33h， 生成 (2R,8R)-(-)-8-methyldecan-2-ol
  参考文献：
  名称：

  Thermostable enzymes in organic synthesis. 7. Total synthesis of the western corn rootworm sex pheromone 8-methyldec-2-yl propanoate using a TBADH-generated C2-bifunctional chiron

  摘要：

  Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.

  DOI：

  10.1021/jo00039a023
• 作为产物：
  描述：

  (R,R)-2,8-Diacetoxy-1,9-dibromononane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以88%的产率得到(2S,8S)-(+)-dihydroxynonane
  参考文献：
  名称：

  A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone

  摘要：

  Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2-dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.

  DOI：

  10.1021/jo00079a024

文献信息

• A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone
  作者：Subhash C. Sinha、Anjana Sinha-Bagchi、Ehud Keinan

  DOI：10.1021/jo00079a024

  日期：1993.12

  Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2-dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.
• Thermostable enzymes in organic synthesis. 7. Total synthesis of the western corn rootworm sex pheromone 8-methyldec-2-yl propanoate using a TBADH-generated C2-bifunctional chiron
  作者：Ehud Keinan、Subhash C. Sinha、Anjana Sinha-Bagchi

  DOI：10.1021/jo00039a023

  日期：1992.6

  Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.