(S)-14-methylhexadecan-1-ol | 10160-00-6

• 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: (S)-14-methylhexadecan-1-ol
• 英文别名: (S)-14-methylhexadecanol；(S)-14-methyl-1-hexadecanol；(S)-14-Methyl-1-hexadecanol；(14S)-14-methylhexadecan-1-ol
• CAS: 10160-00-6
• 化学式: C₁₇H₃₆O
• 分子量: 256.472
• InChiKey: WQBUQCSTGAHNSM-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  18
• 可旋转键数：
  14
• 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)-14-methylhexadecan-1-ol 在 potassium permanganate 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (S)-(+)-14-methylhexadecanoic acid
  参考文献：
  名称：

  Chiral Discrimination of Branched-chain Fatty Acids by Reversed-phase HPLC after Labeling with a Chiral Fluorescent Conversion Reagent

  摘要：

  具有16到29个碳原子的异构脂肪酸被标记为手性荧光转化试剂（1R,2R）和（1S,2S）-2-（2,3-蒽二羧亚胺）环己醇。在低柱温条件下，具有最多20个碳原子的异构酸酯在ODS柱中分为两个峰，而超过21个碳原子的则未被分离。使用C30柱可以分离出C29异构酸的异构酸酯。通过衍生物的洗脱顺序，可以预测每种酸的绝对构型。

  DOI：

  10.1271/bbb.68.153
• 作为产物：
  描述：

  (S)-(+)-14-methylhexadecanoic acid 在 lithium aluminium tetrahydride 作用下， 生成 (S)-14-methylhexadecan-1-ol
  参考文献：
  名称：

  羊毛蜡的成分。第二部分 酸和所述的醇的合成异和（+） - -反异-series

  摘要：

  DOI：

  10.1039/jr9540003344

文献信息

• Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group
  作者：Kenji Mori

  DOI：10.1016/j.tet.2009.02.064

  日期：2009.5

  (R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give

  （- [R）-Trogodermal（14甲基-8-十六碳烯醛），性信息素斑皮蠹属对照存储产品害虫的种类，以及其（小号）通过使用烯烃之间（交叉复分解，合成异构体[R ）-或（S）-7-甲基-1-壬烯和乙酸8-壬烯酯是关键步骤。该步骤对于Grubbs I是成功的，但是对于Grubbs II催化剂却不是成功的。后者导致碳骨架的随机化，从而产生异常产物的混合物，该异常产物具有比所需产物更长或更短的碳链。测量了18种新的和6种先前合成的具有仲仲丁基端基的化合物的比旋光度，得出的结论是[α] D +3.5至+6.5或-3.6至-6.4
• Determination of the Absolute Configurations of the Anteiso Acid Moieties of Glycoglycerolipid S365A Isolated from <i>Corynebacterium aquaticum</i>
  作者：Kazuaki AKASAKA、Seiya SHICHIJYUKARI、Hiroshi MEGURO、Hiroshi OHRUI

  DOI：10.1271/bbb.66.1719

  日期：2002.1.1

  The absolute configurations of the two acid moieties, 12-methyltetradecanoate and 14-methylhexadecanoate, of glycoglycerolipid S365A isolated from Corynebacterium aquaticum were determined by an HPLC analysis after their conversion with the chiral fluorescent labeling reagents, (1S,2S)- and (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanol. Both anteiso acids had the S configuration.

  用手性荧光标记试剂(1S,2S)-和(1R,2R)-2-(2,3-蒽二甲酰亚胺基)环己醇对从水生科里纳菌分离出的甘油酯S365A中的两个酸分子（12-甲基十四酸酯和14-甲基十六酸酯）进行转化后，通过高效液相色谱分析确定了它们的绝对构型。这两种蚁酸都具有 S 构型。
• Prediction of the absolute configuration of optically active pheromones using liquid crystals
  作者：Tetsuya Ikemoto、Kazuhiro Mitsuhashi、Kenji Mori

  DOI：10.1016/s0957-4166(00)80176-7

  日期：1993.4

  Prediction of the absolute configuration of optically active methyl branched pheromones is possible by combining them with mesogens to give them liquid crystalline properties and measuring the helical senses of the chiral nematic phases.
• Murray; Schoenfeld, Journal of the American Oil Chemists' Society, 1952, vol. 29, p. 416,418
  作者：Murray、Schoenfeld

  DOI：——

  日期：——
• Chiral Discrimination of Branched-chain Fatty Acids by Reversed-phase HPLC after Labeling with a Chiral Fluorescent Conversion Reagent
  作者：Kazuaki AKASAKA、Hiroshi OHRUI

  DOI：10.1271/bbb.68.153

  日期：2004.1

  Anteiso fatty acids having 16 to 29 carbon atoms were labeled with the chiral fluorescent conversion reagents, (1R,2R)- and (1S,2S)-2-(2,3-anthracenedicarboximido)cyclohexanol. The diastereomeric esters of anteiso acids having up to 20 carbon atoms were separated into two peaks in an ODS column under low column-temperature conditions, while those having more than 21 carbon atoms were not separated. A C30 column made it possible to separate diastereomeric esters up to C29 anteiso acid. It was possible to predict the absolute configuration of each acid by the elution order of the derivatives.

  具有16到29个碳原子的异构脂肪酸被标记为手性荧光转化试剂（1R,2R）和（1S,2S）-2-（2,3-蒽二羧亚胺）环己醇。在低柱温条件下，具有最多20个碳原子的异构酸酯在ODS柱中分为两个峰，而超过21个碳原子的则未被分离。使用C30柱可以分离出C29异构酸的异构酸酯。通过衍生物的洗脱顺序，可以预测每种酸的绝对构型。