trans-2-heptadecenoic acid ethyl ester | 404573-28-0

• 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: trans-2-heptadecenoic acid ethyl ester
• 英文别名: ethyl (E)-heptadec-2-enoate；(E)-ethylheptadec-2-enoate；ethyl (E)-2-heptadecenoate；ethyl heptadec-2E-enoate
• CAS: 404573-28-0
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: PKOMEGORVJZQCI-ISLYRVAYSA-N

物化性质

• 沸点：
  372.6±11.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-heptadecenoic acid ethyl ester 在 4-二甲氨基吡啶 、 (DHQ)2-PHAL 吡啶 、 盐酸 、 四氧化锇 、 lithium aluminium tetrahydride 、 叠氮化锂 、 草酰氯 、 2,2-DMP 、 sodium hexamethyldisilazane 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 84.0h， 生成 (2S,3S,4S)-2-acetamidooctadecane-1,3,4-triyl triacetate
  参考文献：
  名称：

  Double stereodifferentiation in asymmetric dihydroxylation: application to the first diastereoselective synthesis of l-xylo-[2R,3S,4S]-C18-phytosphingosine

  摘要：

  The first diastereoselective synthesis of L-xylo-(2R,3S 4S)-C-18-phytosphingosine (1) has been achieved by double stereodifferentiation of enantiomerically enriched terminal olefin 14 using (DHQD(2))-PHAL ligand in an asymmetric dihydroxylation with a diastereomeric ratio of 83:17. This phytosphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate 21. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01851-7
• 作为产物：
  描述：

  十五醛 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 1.0h， 以95%的产率得到trans-2-heptadecenoic acid ethyl ester
  参考文献：
  名称：

  Convergent Synthesis of Passifloricin A via a Prins Cyclisation and Olefin Cross-Metathesis Approach

  摘要：

  以Prins环化和复分解反应作为关键步骤，对天然产物passifloricin A的全合成采用立体选择性收敛方法进行了说明。

  DOI：

  10.1055/s-0030-1258253

文献信息

• Structural confirmation of the dihydrosphinganine and fatty acid constituents of the dental pathogen Porphyromonas gingivalis
  作者：JiYoung Mun、Amber Onorato、Frank C. Nichols、Martha D. Morton、Abdullah I. Saleh、Morgan Welzel、Michael B. Smith

  DOI：10.1039/b712707c

  日期：——

  Porphyromonas gingivalis, a recognized periodontal pathogen, is a source of sphinganine bases, fatty acids, free ceramides as well as complex lipids that potentiate interleukin-1b-mediated secretory responses in gingival fibroblasts. The purpose of this study is the structural verification of the sphinganine bases and fatty acids that had been proposed as major components of the complex lipids found in P. gingivalis. The putative C17, C18, and C19 sphinganine bases were prepared from Garner's aldehyde (1) or from a protected serine Weinreb's amide (2). We confirmed that isobranched sphinganine bases are the major structural feature of the ceramides observed from P. gingivalis. We also prepared a C17 unsaturated fatty acid, along with an isobranched C17 3-hydroxy fatty acid, and determined that the major component of the active lipids was the latter.

  牙龈卟啉单胞菌（Porphyromonas gingivalis），一种公认的牙周病原体，是产生丝氨酸基础、脂肪酸、游离神经酰胺以及增强牙龈成纤维细胞中白细胞介素-1β介导的分泌反应的复杂脂质的来源。本研究旨在对先前提出的作为牙龈卟啉单胞菌中发现的复杂脂质主要成分的丝氨酸基础和脂肪酸进行结构验证。假定的C17、C18和C19丝氨酸基础从Garner醛（1）或从保护的丝氨酸Weinreb酰胺（2）中制备。我们确认等分支丝氨酸基础是来自牙龈卟啉单胞菌的神经酰胺观察到的主要结构特征。我们还制备了C17不饱和脂肪酸和一个等分支的C17 3-羟基脂肪酸，并确定活性脂质的主要成分是后者。
• Enantioselective Syntheses of<i>xylo</i>-C₁₈-Phytosphingosines using Double Stereodifferentiation
  作者：Pradeep Kumar、Rodney A. Fernandes

  DOI：10.1055/s-2003-36261

  日期：——

  The concept of double stereodifferentiation in Sharpless asymmetric dihydroxylation has been studied and the results obtained are applied to the diastereoselective syntheses of xylo-isomers of C18-phytosphingosine. The diastereomeric mixture obtained could be separated by column chromatography. Thus, the l-xylo-(2R,3S,4S)-C18- and d-xylo-(2S,3R,4R)-C18-phytosphing­osines as their tetraacetate derivatives were synthesized in dia­stereomerically pure form.

  研究了 Sharpless 不对称二羟基化过程中的双立体异构概念，并将所得结果应用于非对映选择性合成 C18-phytosphingosine 的 xylo 异构体。所获得的非对映异构体混合物可通过柱层析法进行分离。因此，以非对映纯形式合成了 l-xylo-(2R,3S,4S)-C18- 和 d-xylo-(2S,3R,4R)-C18-phytosphingosine 作为它们的四乙酸酯衍生物。
• A novel stereoselective synthesis of pachastrissamine (jaspine B) starting from 1-pentadecanol
  作者：K. Venkatesan、K.V. Srinivasan

  DOI：10.1016/j.tetasy.2007.12.001

  日期：2008.2

  A novel stereoselective synthesis of pachastrissamine (jaspine B), starting from commercially available 1-pentadecanol is described. Sharpless asymmetric dihydroxylation and a chelation controlled vinyl Grignard reaction are the key steps in this synthetic strategy. (C) 2007 Elsevier Ltd. All rights reserved.
• A short enantioselective synthesis of guggultetrol, a naturally occurring lipid
  作者：Shyla George、Gurunath Suryavanshi、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2010.02.019

  日期：2010.3

  An enantioselective synthesis of the naturally occurring lipid, guggultetrol, is described with an overall yield of 24% starting from commercially available 1-pentadecanol in ten linear steps. The key chiral-inducing steps include a Sharpless asymmetric epoxidation of allylic alcohol and a dihydroxylation of an alpha,beta-unsaturated ester. (C) 2010 Elsevier Ltd. All rights reserved.
• A general approach to the enantiomeric synthesis of lipidic α-amino acids, peptides and vicinal amino alcohols
  作者：George Kokotos、JoséM. Padrón、Caterina Noula、William A. Gibbons、Victor S. Martín

  DOI：10.1016/0957-4166(96)00084-5

  日期：1996.3

  A general methodology for the synthesis of saturated lipidic amino acids based on the oxidative cleavage of amino diols obtained by the regioselective opening of enantiomerically enriched 2,3-epoxy alcohols is described. The method opens the way to the synthesis of the enantiomers of lipidic 2-amino alcohols and home- and hetero-peptides. (C) 1996 Elsevier Science Ltd