(S)-4-壬醇 | 52708-03-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-4-壬醇
• 英文名称: (S)-4-nonanol
• 英文别名: (+)-4-nonanol；(4S)-nonan-4-ol
• CAS: 52708-03-9
• 化学式: C₉H₂₀O
• 分子量: 144.257
• InChiKey: IXUOEGRSQCCEHB-VIFPVBQESA-N

物化性质

• 熔点：
  6.15°C (estimate)
• 沸点：
  192.9°C (estimate)
• 密度：
  0.8282

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-4-壬醇 在 甲醇 、 platinum(IV) oxide 、 sodium azide 、 氢碘酸 作用下， 60.0 ℃ 、294.18 kPa 条件下， 生成 (+)(S)-4-amino-nonane
  参考文献：
  名称：

  Levene; Kuna, Journal of Biological Chemistry, 1941, vol. 140, p. 256

  摘要：

  DOI：
• 作为产物：
  描述：

  4-壬醇 生成 (S)-4-壬醇
  参考文献：
  名称：

  Levene; Kuna, Journal of Biological Chemistry, 1941, vol. 140, p. 256

  摘要：

  DOI：

文献信息

• Asymmetric synthesis via chiral silicon reagents. Chiral α-hydroxyalkyl anion equivalents from vinylsilanes containing optically active amino or alkoxy groups on silicon
  作者：Kohei Tamao、Ryuichiro Kanatani、Makoto Kumada

  DOI：10.1016/s0040-4039(01)90074-7

  日期：1984.1

  Chiral vinylsilanes containing optically active functional groups on silicon have been used as precursors for chiral α-hydroxyalkyl anion equivalents via a sequence of addition of η-butyllithium, coupling with organic halides, and oxidative cleavage of the silicon-carbon bond, to give optically active alcohols of up to 60% ee.

  通过添加η-丁基锂，与有机卤化物偶合以及硅-碳键的氧化裂解的顺序，已将硅上含有旋光性官能团的手性乙烯基硅烷用作手性α-羟烷基阴离子当量的前体。酒精含量高达ee的60％。
• The Solvent Effects on the Optical Rotatory Properties of 1,7-Diaryl-5-hydroxy-3-heptanones and Related Compounds
  作者：Shinji Ohta

  DOI：10.1246/bcsj.59.1181

  日期：1986.4

  the intramolecular hydrogen bond followed by solvation to the carbonyl and/or hydroxyl groups, as well as the presence of the phenyl groups. The ca. 30% of the solvent effect on the optical rotation was based on the change in the rotational strength associated with the n→π∗ transition of the carbonyl group as changing a solvent. The residual 70% was based on the change in the rotational strength associated

  (S)-1,7-二苯基-5-羟基-3-庚酮、(S)-1,7-双(3,4-二甲氧基苯基)-5-羟基-3-庚酮的ORD和CD曲线，以及相关模型化合物是在选定的不同极性溶剂中获得的。导致 1,7-二芳基-5-羟基-3-庚酮在氯仿中右旋的原因是在 C-3 羰基和 C-5 羟基之间形成了分子内氢键，无论是否存在苯基组。另一方面，证明使化合物在甲醇中左旋需要同时破坏分子内氢键，然后溶剂化到羰基和/或羟基，以及苯基的存在。约。30% 的溶剂对旋光度的影响是基于随着溶剂的变化，与羰基的 n→π* 转变相关的旋转强度的变化。剩余的 70% 是基于与电子跃迁相关的旋转强度的变化......
• Titanocene-Catalyzed Regiodivergent Epoxide Openings
  作者：Andreas Gansäuer、Chun-An Fan、Florian Keller、Jutta Keil

  DOI：10.1021/ja0686211

  日期：2007.3.1

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.
• Chiral allenylboronic esters: a practical reagent for enantioselective carbon-carbon bond formation
  作者：Ryuichi Haruta、Masaharu Ishiguro、Nobuo Ikeda、Hisashi Yamamoto

  DOI：10.1021/ja00390a052

  日期：1982.12
• Chemoenzymatic synthesis of α-halogeno-3-octanol and 4-or 5-nonanols. Application to the preparation of chiral epoxides
  作者：Pascale Besse、Tania Sokoltchik、Henri Veschambre

  DOI：10.1016/s0957-4166(98)00470-4

  日期：1998.12

  A study of the microbiological reduction of different alpha-halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.