2-tert-butyl-2-hydroxymethyl-4-methyl-1,3-pentanediol | 253351-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butyl-2-hydroxymethyl-4-methyl-1,3-pentanediol
• CAS: 253351-88-1
• 化学式: C₁₁H₂₄O₃
• 分子量: 204.31
• InChiKey: ULFBHPOJLZYIMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-2-hydroxymethyl-4-methyl-1,3-pentanediol 在 吡啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以39%的产率得到4-tert-butyl-3-isopropyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfide
  参考文献：
  名称：

  Bicyclophosphorothionate antagonists exhibiting selectivity for housefly GABA receptors

  摘要：

  2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfides (bicyclophosphorothionates) with various C1-4 alkyl groups at the 3- and 4-positions were synthesized and tested for their ability to compete with [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a non-competitive antagonist of gamma-aminobutyric acid (GABA) receptors, for specific binding to rat-brain and housefly-head membranes, and for their insecticidal activity against houseflies. Among the 3,4-substituted analogues, 20 compounds were selectively active for housefly GABA receptors versus rat GABA receptors. The 3-alkyl groups of C-3 length and the 4-alkyl groups of C-4 length were tolerated in housefly receptors, whereas such bulky substituents were deleterious in rat receptors. The 4-isobutyl-3-isopropyl analogue was the most potent in housefly receptors (IC50 = 45.2 nM), and tert-butylbicyclophosphorothionate (TBPS), with the 4-tert-butyl group and no 3-substituent, was the most potent in rat receptors (IC50 = 62.2 nM). Their receptor selectivities (rat IC50/housefly IC50) were 52 and 0.038, respectively. The insecticidal activity (LD50) of 20 active analogues was well correlated with their potency (IC50) in inhibiting [H-3]EBOB binding to housefly-head membranes (r = 0.93). The results obtained in the present study indicate that the introduction of appropriate alkyl groups into the 3- and ii-positions of bicyclophosphorothionate leads to non-competitive antagonists with increased affinity and selectivity for housefly ionotropic GABA receptors versus rat GABAA receptors. (C) 1999 Society of Chemical Industry.

  DOI：

  10.1002/(sici)1096-9063(199910)55:10<971::aid-ps49>3.0.co;2-j
• 作为产物：
  描述：

  diethyl tert-butyl(hydroxymethyl)malonate 在 lithium aluminium tetrahydride 、 sodium acetate 、 lithium 、 对甲苯磺酸 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 58.0h， 生成 2-tert-butyl-2-hydroxymethyl-4-methyl-1,3-pentanediol
  参考文献：
  名称：

  Bicyclophosphorothionate antagonists exhibiting selectivity for housefly GABA receptors

  摘要：

  2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfides (bicyclophosphorothionates) with various C1-4 alkyl groups at the 3- and 4-positions were synthesized and tested for their ability to compete with [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a non-competitive antagonist of gamma-aminobutyric acid (GABA) receptors, for specific binding to rat-brain and housefly-head membranes, and for their insecticidal activity against houseflies. Among the 3,4-substituted analogues, 20 compounds were selectively active for housefly GABA receptors versus rat GABA receptors. The 3-alkyl groups of C-3 length and the 4-alkyl groups of C-4 length were tolerated in housefly receptors, whereas such bulky substituents were deleterious in rat receptors. The 4-isobutyl-3-isopropyl analogue was the most potent in housefly receptors (IC50 = 45.2 nM), and tert-butylbicyclophosphorothionate (TBPS), with the 4-tert-butyl group and no 3-substituent, was the most potent in rat receptors (IC50 = 62.2 nM). Their receptor selectivities (rat IC50/housefly IC50) were 52 and 0.038, respectively. The insecticidal activity (LD50) of 20 active analogues was well correlated with their potency (IC50) in inhibiting [H-3]EBOB binding to housefly-head membranes (r = 0.93). The results obtained in the present study indicate that the introduction of appropriate alkyl groups into the 3- and ii-positions of bicyclophosphorothionate leads to non-competitive antagonists with increased affinity and selectivity for housefly ionotropic GABA receptors versus rat GABAA receptors. (C) 1999 Society of Chemical Industry.

  DOI：

  10.1002/(sici)1096-9063(199910)55:10<971::aid-ps49>3.0.co;2-j