(R)-methyl 2-hydroxytetradecanoate | 56009-40-6

• 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: (R)-methyl 2-hydroxytetradecanoate
• 英文别名: methyl (2R)-2-hydroxytetradecanoate
• CAS: 56009-40-6；130823-84-6；149948-88-9；149948-89-0
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: ATFSJSYRBAGGIS-CQSZACIVSA-N

物化性质

• 沸点：
  304.1±10.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-hydroxytetradecanoate 在 lithium aluminium tetrahydride 作用下， 生成 1,2-十四烷二醇
  参考文献：
  名称：

  Horn et al., Journal of the Chemical Society, 1954, p. 177,179

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]tetradecanamide 在 盐酸 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 3.0h， 生成 (R)-methyl 2-hydroxytetradecanoate
  参考文献：
  名称：

  Cerebrosides fromfomitopsis pinicola (Sw. Ex Fr.) Karst.

  摘要：

  A cerebroside fraction was obtained from the fruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC. The sugar component of all cerebrosides was D-glucose. The major fatty acids were 2-hydroxyfatty acids (C-14-C-18), the long chain base was identified as 9-methyl-C-18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi. Based on degradation studies, fast atom bombardment mass spectrometry, and different H-1 and C-13 NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-beta-D-glucopyranosyl-9-methyl-4,8-sphingadienine.

  DOI：

  10.1007/bf00817267

文献信息

• Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
  作者：Zechao Lin、Jiahong Li、Qingfei Huang、Qiuya Huang、Qiwei Wang、Lei Tang、Deying Gong、Jun Yang、Jin Zhu、Jingen Deng

  DOI：10.1021/acs.joc.5b00241

  日期：2015.5.1

  ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π

  设计并合成了一系列两亲性配体。具有配体的铑配合物被用于纯水中宽范围的长链脂族酮酸酯的不对称转移氢化。使用手性表面活性剂型催化剂2观察到α-，β-，γ-，δ-和ε-酮酸酯以及α-和β-酰氧基酮的定量转化率和出色的对映选择性（高达99％ee）。在金属硅油核中，催化剂与底物之间的长脂肪链之间的CH /π相互作用和长脂肪链的强疏水相互作用在催化过渡态中起着关键作用。胶束中金属催化位点与核心的疏水微环境之间的协同作用有助于实现高立体选择性。
• New Cytotoxic Secondary Metabolites from Marine Bryozoan Cryptosula pallasiana
  作者：Xiang-Rong Tian、Yan-Qing Gao、Xiao-Lin Tian、Jiao Li、Hai-Feng Tang、Yu-Shan Li、Hou-Wen Lin、Zhi-Qing Ma

  DOI：10.3390/md15040120

  日期：——

  dichroism (ECD) calculations. Among the isolated compounds, sterol 1 possessed a rare side chain with a methoxy group at C-23, and a double bond between C-24 and C-25. Ceramides 6 and 7 possessed 14 carbons in their long-chain fatty acid base (FAB), which were different from the normal ceramides with 16 carbons in the FAB. Moreover, compounds 5 and 8 were isolated for the first time from marine bryozoans

  一种新的固醇，（23R）-甲氧基胆甾-5,24-二烯-3β-醇（1），两种新的神经酰胺，（2S，3R，4E，8E）-2-（十四烷酰氨基）-4,8-​​十八碳烯基-1 ，3-二醇（6）和（2S，3R，2'R，4E，8E）-2-（十四烷酰氨基）-4,8-​​十八烷基-1,3,2'-三醇（7），以及三个已知的从中国黄岛采集的海洋苔藓虫隐孢子虫（Cryptosula pallasiana）中分离出甾醇（2-4），内酯（5）和两种神经酰胺（8,9）。通过广泛的光谱分析，化学方法和量子电子圆二色性（ECD）计算，阐明了新化合物的结构。在分离的化合物中，固醇1具有在C-23具有甲氧基的稀有侧链以及在C-24和C-25之间的双键。神经酰胺6和7在其长链脂肪酸碱（FAB）中具有14个碳，与FAB中含16个碳的普通神经酰胺不同。此外，化合物5和8首次从海洋苔藓动物中分离出来。评价化合物1-9对人肿瘤细胞系HL