(R)-(-)-2-(oleoyloxymethyl)oxirane | 849589-86-2

• 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)-(-)-2-(oleoyloxymethyl)oxirane
• 英文别名: Glycidyl oleate, (R)-；[(2R)-oxiran-2-yl]methyl (Z)-octadec-9-enoate
• CAS: 849589-86-2
• 化学式: C₂₁H₃₈O₃
• 分子量: 338.531
• InChiKey: VWYIWOYBERNXLX-GDCKJWNLSA-N

物化性质

• 沸点：
  430.3±28.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(oleoyloxymethyl)oxirane 在 吡啶 、 甲醇 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 5.33h， 生成 (R)-2,3-dihydroxypropyl (Z)-9-octadecenoate
  参考文献：
  名称：

  Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols

  摘要：

  Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sii-glycerols can be obtained directly in high purity (>99%) and in quantitative yields. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.093

文献信息

• Regioselective and Stereospecific Halosilylating Cleavage of the Oxirane System of Glycidol Derivatives as an Efficient Strategy to C2-O-Functionalized C3-Vicinal Halohydrins
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1002/ejoc.200800112

  日期：2008.5

  andstereospecific opening of the oxirane ring upon treatment with trimethylsilyl halides (TMSX, X = Cl, Br, or I) in the presence of pyridine to produce the corresponding C2-O-trimethylsilyl-3(1)-halo-sn-glycerols in high yields. Trifluoroacetylation across the trimethylsilyloxy system of such C3-synthons with trifluoroacetic anhydride (TFAA) in the presence of a halide anion (e.g. Bu4NX; X = Cl, Br, or I), followed

  缩水甘油酯和醚在吡啶存在下用三甲基甲硅烷基卤化物（TMSX、X = Cl、Br 或 I）处理环氧乙烷环发生区域选择性和立体特异性打开，生成相应的 C2-O-三甲基甲硅烷基-3(1)-高产率的 halo-sn-甘油。在卤化物阴离子（例如 Bu4NX；X = Cl、Br 或 I）存在下，使用三氟乙酸酐 (TFAA) 在此类 C3 合成子的三甲基甲硅烷氧基系统上进行三氟乙酰化，然后去除三氟乙酰瞬态保护，提供近乎定量的访问到相应的邻位卤代烷醇。或者，C2-O-酰化邻位卤代醇可以以高度化学/区域特异性的方式通过三甲基甲硅烷基保护基团直接转化为短链或长链酯官能团，通过三组分试剂获得：吡啶-羧酸-TFAA。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Efficient, highly regioselective, and stereospecific conversion of glycidol systems into C2-O-acylated vicinal halohydrins
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1016/j.tetlet.2006.02.050

  日期：2006.4

  Glycidyl esters and ethers undergo a regioselective and stereospecific opening of the oxirane ring upon treatment in chloroform in the presence of pyridine with trimethylsilyl halide (TMSX, X = Cl, Br, or I) and a mixture of carboxylic acid (CA)–trifluoroacetic anhydride (TFAA), to produce the corresponding C2-O-acylated vicinal halohydrins in high yields.

  吡啶与三甲基甲硅烷基卤化物（TMSX，X = Cl，Br或I）和羧酸（CA）-三氟乙酸酐的混合物在吡啶存在下，在氯仿中处理时，缩水甘油酯和醚会发生环氧乙烷环的区域选择性和立体选择性开环（TFAA），以高产率产生相应的C 2 -O-酰化的邻位卤代醇。
• Regioselective and stereospecific cleavage of a terminal oxirane system: A novel synthetic approach to lipid mediator congeners—1,2(2,3)-diacyl-3(1)-halo-sn-glycerols
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1016/j.bmcl.2006.04.040

  日期：2006.7

  upon treatment with a mixture of carboxylic acid anhydride (CAA) and trimethylsilyl halide (TMSX) in the presence of tetra-n-butylammonium halide (Bu(4)NX, X=Cl, Br or I) undergo stereospecific and regioselective opening of the oxirane ring to afford mixed-(or mono)-acid 1,2(2,3)-diacyl-3(1)-halo-sn-glycerols in high yields.

  在四正丁基卤化铵（Bu（4）NX，X = Cl，Br或I）存在下用羧酸酐（CAA）和三甲基甲硅烷基卤化物（TMSX）的混合物处理后的缩水甘油酯经历立体定向和区域选择性开放环氧乙烷环生成高产率的混合（或单）酸1,2（2,3）-二酰基-3（1）-卤代-sn-甘油。
• Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1039/b713246h

  日期：——

  acyl residue at the central carbon of the silylated synthons with a subsequent Et(3)N.3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment

  三氟乙酸催化带有三氟乙酸酐（TFAA）的带有烯丙基酰基或烷基官能团的缩水甘油基衍生物的环氧乙烷环的开环，可有效进入构型均质的1（3）-酰基-或1（3）-O-烷基-sn -甘油。在这些关键中间体的末端位置选择性引入叔丁基二甲基甲硅烷基-（TBDMS）或三异丙基甲硅烷基-（TIPS）瞬态保护可确保1（3）-酰基-或1（3）-O-烷基-3（1）- O-TBDMS（或TIPS）-sn-甘油作为1,2（2,3）-二酰基-，1（3）-O-烷基-2-酰基-和1,3-二酰基-sn-的一般双功能前体甘油和三酯等排体。通过三氯乙酸酐（TCAA）在甲硅烷基化的合成子的中央碳原子上引入必要的酰基残基，并随后进行Et（3）N.3HF促进的，直接的三氯乙酰化作用穿过硅烷氧基体系 然后裂解三氯乙酰基，得到各自的1,2（2,3）-二酰基-或1（3）-O-烷基-2-酰基-sn-甘油。可选择地，反应序列包括：（i）三氯乙酰基片段连接在单甲硅烷基化甘油酯的立体C
• Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1016/j.tetlet.2005.01.093

  日期：2005.3

  Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sii-glycerols can be obtained directly in high purity (>99%) and in quantitative yields. (C) 2005 Elsevier Ltd. All rights reserved.