(S)-2-methyloctadecanoic acid | 60491-04-5

• 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)-2-methyloctadecanoic acid
• 英文别名: (2S)-2-Methyloctadecanoic acid
• CAS: 60491-04-5
• 化学式: C₁₉H₃₈O₂
• 分子量: 298.51
• InChiKey: GBZDALHFANHWOF-SFHVURJKSA-N

物化性质

• 熔点：
  54.7-55.0 °C
• 沸点：
  415.3±13.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-methyloctadecanoic acid 在 lithium aluminium tetrahydride 、 氢碘酸 作用下， 生成 (S)-1-Iodo-2-methyl-octadecane
  参考文献：
  名称：

  Synthesis of the stereoisomers of 17,21-dimethylheptatriacontane - sex recognition pheromone of the tsetse fly

  摘要：

  DOI：

  10.1016/s0040-4039(01)83933-2
• 作为产物：
  描述：

  Pentadecylmagnesium Bromide 在 dilithium tetrachlorocuprate 、 lithium hydroxide monohydrate 、 C₃₈H₄₀IrNP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， -20.0~80.0 ℃ 、607.99 kPa 条件下， 反应 25.0h， 生成 (S)-2-methyloctadecanoic acid
  参考文献：
  名称：

  铱催化α-取代丙烯酸的不对称加氢迭代合成聚脱氧丙酸酯

  摘要：

  基于铱催化的α-取代丙烯酸的不对称加氢反应，开发了一种新型的合成聚脱氧丙酸酯的迭代方案。催化剂的负载量可低至0.01 mol％，并且一个迭代循环的总收率> 76％。反应条件温和，不需要有机金属试剂或色谱步骤。使用此协议，以高收率合成了（+）-苯硫cer酸和离子霉素和硼瑞林的聚脱氧丙酸酯基序。

  DOI：

  10.1021/acs.orglett.8b01193

文献信息

• Synthetic Studies toward <i>Mycobacterium tuberculosis</i> Sulfolipid-I
  作者：Clifton D. Leigh、Carolyn R. Bertozzi

  DOI：10.1021/jo702032c

  日期：2008.2.1

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.
• Staellberg, Arkiv foer Kemi, 1958, vol. 12, p. 153,157
  作者：Staellberg

  DOI：——

  日期：——
• Synthesis of a <i>Mycobacterium tuberculosis</i> Tetra-acylated Sulfolipid Analogue and Characterization of the Chiral Acyl Chains Using Anisotropic NAD 2D-NMR Spectroscopy
  作者：Aurélie Lemétais、Yann Bourdreux、Philippe Lesot、Jonathan Farjon、Jean-Marie Beau

  DOI：10.1021/jo4012255

  日期：2013.8.2

  Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated trehalose sulfate derivatives having simple acyl chains. The trehalose core was regioselectively protected using a tandem procedure with catalytic iron(III) chloride hexahydrate and further desymmetrized. Model chiral fatty acids, prepared by a zinc-mediated cross-coupling, were incorporated into the trehalose core. The enantiomeric excess of the chiral fatty acids has been measured by natural abundance deuterium (NAD) 2D-NMR spectroscopy in a polypeptide based chiral liquid crystal. The synthetic approach established for the model compounds can easily be developed for the preparation of other analogues and natural sulfolipids.
• Synthesis of Diacylated Trehalose Sulfates: Candidates for a Tuberculosis Vaccine
  作者：Julie Guiard、Anthony Collmann、Martine Gilleron、Lucia Mori、Gennaro De Libero、Jacques Prandi、Germain Puzo

  DOI：10.1002/anie.200803835

  日期：2008.12.1
• Iterative Synthesis of Polydeoxypropionates Based on Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted Acrylic Acids
  作者：Wen Che、Danyang C. Wen、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.8b01193

  日期：2018.6.1

  for the synthesis of polydeoxypropionates was developed based on iridium-catalyzed asymmetric hydrogenation of α-substituted acrylic acids. The catalyst loading can be as low as 0.01 mol %, and the overall yield for one iterative cycle is >76%. The reaction conditions are mild, and no organometallic reagents or chromatography steps are required. Using this protocol, (+)-phthioceranic acid and the polydeoxypropionate

  基于铱催化的α-取代丙烯酸的不对称加氢反应，开发了一种新型的合成聚脱氧丙酸酯的迭代方案。催化剂的负载量可低至0.01 mol％，并且一个迭代循环的总收率> 76％。反应条件温和，不需要有机金属试剂或色谱步骤。使用此协议，以高收率合成了（+）-苯硫cer酸和离子霉素和硼瑞林的聚脱氧丙酸酯基序。