2-methoxy-4-oleoyloxy-1,2-oxaphosphorinan-5-ol 2-oxide

• 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: 2-methoxy-4-oleoyloxy-1,2-oxaphosphorinan-5-ol 2-oxide
• 英文别名: [(4R,5R)-5-hydroxy-2-methoxy-2-oxo-1,2lambda5-oxaphosphinan-4-yl] (Z)-octadec-9-enoate；[(4R,5R)-5-hydroxy-2-methoxy-2-oxo-1,2λ5-oxaphosphinan-4-yl] (Z)-octadec-9-enoate
• 化学式: C₂₃H₄₃O₆P
• 分子量: 446.565
• InChiKey: LJAYQGVCXYMPTD-JNLCEWKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxy-4-oleoyloxy-1,2-oxaphosphorinan-5-ol 2-oxide 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到2,5-dihydroxy-4-oleoyloxy-1,2-oxaphosphorinane 2-oxide
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction

  摘要：

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.

  DOI：

  10.1021/jo0607919
• 作为产物：
  描述：

  油酸 、 2-methoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以38%的产率得到2-methoxy-4-oleoyloxy-1,2-oxaphosphorinan-5-ol 2-oxide
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction

  摘要：

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.

  DOI：

  10.1021/jo0607919

文献信息

• Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction
  作者：Honglu Zhang、Ryoko Tsukuhara、Gabor Tigyi、Glenn D. Prestwich

  DOI：10.1021/jo0607919

  日期：2006.8.1

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.