(6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid | 1312784-18-1

• 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: (6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid
• 英文别名: (6S,9R,10S,E)-6,9,10-trihydroxyoctadec-7-enoic acid；oxylipin；(6S,9R,10S)-6,9,10-trihydroxyoctadec-7E-enoic acid；(E,6S,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid
• CAS: 1312784-18-1
• 化学式: C₁₈H₃₄O₅
• 分子量: 330.465
• InChiKey: KFPLVZLISLBBSJ-SYMVGPSASA-N

物化性质

• 沸点：
  543.4±50.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid 、 4-硝基苄胺盐酸盐 在 BOP-BF4 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense

  摘要：

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

  DOI：

  10.1021/ol501263y
• 作为产物：
  描述：

  6-(苄氧基)-1-己醇 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) isopropylate 、 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 碘苯二乙酸 、 碘 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 31.33h， 生成 (6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid
  参考文献：
  名称：

  立体选择性全合成脂蛋白：（6S，7E，9R，10S）‐6,9,10‐三羟基十八烷基‐7-烯酸和（6Z，8R，9R，10S）‐8,9,10‐三羟基十八烷基‐6-‐烯酸酸

  摘要：

  氧脂素的立体选择性全合成图1B和图1C是从容易获得天然糖开始描述通过该格鲁布斯交叉复分解，维悌希烯化反应，和Zn介导的还原消除作为关键步骤。

  DOI：

  10.1002/hlca.201300223

文献信息

• Three-step synthesis of oxylipins from D. loretense
  作者：Shreyosree Chatterjee、Gayan A. Abeykoon、Jason S. Chen

  DOI：10.1016/j.tetlet.2019.06.040

  日期：2019.7

  A three-step convergent synthesis of an immunostimulatory oxylipin was developed using an olefin cross metathesis approach. The alkene fragments were prepared in two steps from commercially available starting materials with high stereoselectivity. In particular, an organocatalytic aldehyde α-oxygenation gave high enantioselectivity and yield using as little as 2 mol% catalyst. This synthesis represents

  使用烯烃交叉复分解方法开发了免疫刺激性磷脂的三步收敛合成法。用高立体选择性从市售起始原料分两步制备烯烃片段。特别地，使用少至2mol％的催化剂，有机催化的醛α-氧化给出了高的对映选择性和收率。该合成代表了任何含有3-ene-1,2,5-三醇部分的天然产物的最短合成，并以33％的总收率递送了免疫刺激性的脂蛋白。
• First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid
  作者：Sucheta Chatterjee、Seema V. Kanojia、Subrata Chattopadhyay、Anubha Sharma

  DOI：10.1016/j.tetasy.2011.02.008

  日期：2011.2

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective Total Synthesis of Oxylipins: (6<i>S</i>,7<i>E</i>,9<i>R</i>,10<i>S</i>)-6,9,10-Trihydroxyoctadec-7-enoic Acid and (6<i>Z</i>,8<i>R</i>,9<i>R</i>,10<i>S</i>)-8,9,10-Trihydroxyoctadec-6-enoic Acid
  作者：Jhillu Singh Yadav、Kattela Shiva Shankar、Anugu Srinivas Reddy、Basi V. Subba Reddy

  DOI：10.1002/hlca.201300223

  日期：2014.4

  The stereoselective total syntheses of oxylipins 1b and 1c are described starting from readily accessible natural sugars via the Grubbs cross‐metathesis, Wittig olefination, and Zn‐mediated reductive elimination as key steps.

  氧脂素的立体选择性全合成图1B和图1C是从容易获得天然糖开始描述通过该格鲁布斯交叉复分解，维悌希烯化反应，和Zn介导的还原消除作为关键步骤。
• <i>anti</i>-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from <i>Dracontium loretense</i>
  作者：Gayan A. Abeykoon、Shreyosree Chatterjee、Jason S. Chen

  DOI：10.1021/ol501263y

  日期：2014.6.20

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.