Hexadecanoic acid (1R,2S,3S)-2-hexadecanoyloxymethyl-3-hydroxymethyl-cyclopropylmethyl ester | 649764-91-0

• 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: Hexadecanoic acid (1R,2S,3S)-2-hexadecanoyloxymethyl-3-hydroxymethyl-cyclopropylmethyl ester
• CAS: 649764-91-0
• 化学式: C₃₈H₇₂O₅
• 分子量: 608.987
• InChiKey: NPSNKUTVOKEMAP-DNZQSCRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.89
• 重原子数：
  43.0
• 可旋转键数：
  33.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (1R,2S,3S)-2-hexadecanoyloxymethyl-3-hydroxymethyl-cyclopropylmethyl ester 在 platinum(IV) oxide 咪唑 、 氢气 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 22.0h， 生成 Hexadecanoic acid (1S,2R,3R)-2-hexadecanoyloxymethyl-3-phosphonooxymethyl-cyclopropylmethyl ester
  参考文献：
  名称：

  Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids

  摘要：

  Short synthetic routes are described to produce structurally related phospholipids that are either conformationally restricted or flexible. The conformationally restricted structures have a cyclopropyl ring in the interfacial region of the phospholipid. The key synthetic step is a cyclopropanation reaction between 2(5H)-furanone and a stabilized chloroallylic phosphonate anion. The synthetic routes enable the incorporation of different polar headgroups as well as nonpolar tails at late stages in the sequence. The phosphoethanolamine derivatives 1b and 2b readily form encapsulating vesicles, however, dye leakage from vesicles composed of the restricted phospholipid 1b is significantly slower than from vesicles composed of flexible analogue 2b. Physicochemical analyses using P-31 NMR, differential scanning calorimetry, fluorescence anisotropy, and Langmuir-Blodgett films suggest that the decreased permeability of membranes composed of conformationally restricted 1b is due to its ability to pack more closely in a bilayer assembly.

  DOI：

  10.1021/jo034843v
• 作为产物：
  描述：

  6-(tert-butyl-diphenyl-silyloxymethyl)-3-oxa-bicyclo[3.1.0]hexane-2-one 在 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.67h， 生成 Hexadecanoic acid (1R,2S,3S)-2-hexadecanoyloxymethyl-3-hydroxymethyl-cyclopropylmethyl ester
  参考文献：
  名称：

  Synthesis and Supramolecular Properties of Conformationally Restricted and Flexible Phospholipids

  摘要：

  Short synthetic routes are described to produce structurally related phospholipids that are either conformationally restricted or flexible. The conformationally restricted structures have a cyclopropyl ring in the interfacial region of the phospholipid. The key synthetic step is a cyclopropanation reaction between 2(5H)-furanone and a stabilized chloroallylic phosphonate anion. The synthetic routes enable the incorporation of different polar headgroups as well as nonpolar tails at late stages in the sequence. The phosphoethanolamine derivatives 1b and 2b readily form encapsulating vesicles, however, dye leakage from vesicles composed of the restricted phospholipid 1b is significantly slower than from vesicles composed of flexible analogue 2b. Physicochemical analyses using P-31 NMR, differential scanning calorimetry, fluorescence anisotropy, and Langmuir-Blodgett films suggest that the decreased permeability of membranes composed of conformationally restricted 1b is due to its ability to pack more closely in a bilayer assembly.

  DOI：

  10.1021/jo034843v