Tricosa-10,12-diynoic acid (R)-2-(diethoxy-phosphoryl)-1-tricosa-10,12-diynoyloxymethyl-ethyl ester | 406207-29-2

• 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: Tricosa-10,12-diynoic acid (R)-2-(diethoxy-phosphoryl)-1-tricosa-10,12-diynoyloxymethyl-ethyl ester
• CAS: 406207-29-2
• 化学式: C₅₃H₈₉O₇P
• 分子量: 869.259
• InChiKey: XHCUHVYGLZFMEN-NLXJDERGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.02
• 重原子数：
  61.0
• 可旋转键数：
  41.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Tricosa-10,12-diynoic acid (R)-2-(diethoxy-phosphoryl)-1-tricosa-10,12-diynoyloxymethyl-ethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 7.5h， 以98%的产率得到
  参考文献：
  名称：

  Phosphonate Lipid Tubules II

  摘要：

  We describe a new chiral tubule-forming lipid in which the C-O-P phosphoryl linkage of the archetypal tubule-forming molecule, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, "DC(8,9)PC", is replaced by a C-P linkage. Tubule formation with this phosphonate analogue proceeds under the same mild conditions as with DC(8,9)PC and produces similar yields, but synchrotron small-angle X-ray scattering, atomic force microscopy, and optical microscopy show the new tubules to have diameters 1.94 times as great, to be significantly shorter, and to be thinner-walled. A significant portion of the enantiomerically pure chiral phosphonate precipitate is in the form of stable open helices, and these helices are divided almost evenly between left- and right-handed members.

  DOI：

  10.1021/ja012137a
• 作为产物：
  描述：

  diethyl [(R)-O-3,4-isopropylidene-3,4-dihydroxypropyl]phosphonate 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 Tricosa-10,12-diynoic acid (R)-2-(diethoxy-phosphoryl)-1-tricosa-10,12-diynoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Phosphonate Lipid Tubules II

  摘要：

  We describe a new chiral tubule-forming lipid in which the C-O-P phosphoryl linkage of the archetypal tubule-forming molecule, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, "DC(8,9)PC", is replaced by a C-P linkage. Tubule formation with this phosphonate analogue proceeds under the same mild conditions as with DC(8,9)PC and produces similar yields, but synchrotron small-angle X-ray scattering, atomic force microscopy, and optical microscopy show the new tubules to have diameters 1.94 times as great, to be significantly shorter, and to be thinner-walled. A significant portion of the enantiomerically pure chiral phosphonate precipitate is in the form of stable open helices, and these helices are divided almost evenly between left- and right-handed members.

  DOI：

  10.1021/ja012137a