1-arachidonylglycerol 2,3-phenylboronate ester | 286834-30-8

• 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: 1-arachidonylglycerol 2,3-phenylboronate ester
• 英文别名: (2-phenyl-1,3,2-dioxaborolan-4-yl)methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 286834-30-8
• 化学式: C₂₉H₄₁BO₄
• 分子量: 464.453
• InChiKey: RARYJFSAFCJPJS-DOFZRALJSA-N

物化性质

• 沸点：
  577.0±50.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-arachidonylglycerol 2,3-phenylboronate ester 在 水 作用下， 以 甲醇 为溶剂， 生成 2-arachidonyl-glycerol
  参考文献：
  名称：

  Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3-phenylboronate ester

  摘要：

  2-Arachidonylglycerol (2-Ara-Gl) was synthesized via the intermediacy of its 1,3-phenylboronic acid ester. The boronate ester is easily stable enough to enable chromatographic resolution from the corresponding 1-Ara-Gl boronate ester on normal phase elution yet immediately and completely hydrolyzes to 2-Ara-Gl and phenylboronic acid, without isomerization, by simple solution in aqueous-organic solvents. The phenylboronate ester of this 2-acylglycerol has the added advantage of being markedly more stable to both isomerization and oxidation upon storage than the labile 2-Ara-Gl. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00469-x
• 作为产物：
  描述：

  花生四烯酸 在 草酰氯 、 硼酸三乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-arachidonylglycerol 2,3-phenylboronate ester
  参考文献：
  名称：

  Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3-phenylboronate ester

  摘要：

  2-Arachidonylglycerol (2-Ara-Gl) was synthesized via the intermediacy of its 1,3-phenylboronic acid ester. The boronate ester is easily stable enough to enable chromatographic resolution from the corresponding 1-Ara-Gl boronate ester on normal phase elution yet immediately and completely hydrolyzes to 2-Ara-Gl and phenylboronic acid, without isomerization, by simple solution in aqueous-organic solvents. The phenylboronate ester of this 2-acylglycerol has the added advantage of being markedly more stable to both isomerization and oxidation upon storage than the labile 2-Ara-Gl. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00469-x

文献信息

• Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3-phenylboronate ester
  作者：Herbert H Seltzman、Denise N Fleming、Gregory D Hawkins、F.Ivy Carroll

  DOI：10.1016/s0040-4039(00)00469-x

  日期：2000.5

  2-Arachidonylglycerol (2-Ara-Gl) was synthesized via the intermediacy of its 1,3-phenylboronic acid ester. The boronate ester is easily stable enough to enable chromatographic resolution from the corresponding 1-Ara-Gl boronate ester on normal phase elution yet immediately and completely hydrolyzes to 2-Ara-Gl and phenylboronic acid, without isomerization, by simple solution in aqueous-organic solvents. The phenylboronate ester of this 2-acylglycerol has the added advantage of being markedly more stable to both isomerization and oxidation upon storage than the labile 2-Ara-Gl. (C) 2000 Elsevier Science Ltd. All rights reserved.