dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate | 107024-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate
• 英文别名: Dimethyl 3-[4-(t-butyldimethylsiloxy)phenyl]-2-oxo-butylphosphonate；3-[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]-1-dimethoxyphosphorylbutan-2-one
• CAS: 107024-78-2
• 化学式: C₁₈H₃₁O₅PSi
• 分子量: 386.5
• InChiKey: JQQGBZCMFSLTCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate 在 lithium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.17h， 生成 <1S-<1α,2α,(Z),3α(1E,3S^*,4R^*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homoprosta-5-enoic acid analogs as thromboxane A2 receptor antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha, 2 alpha(Z),3 alpha(1E,3S*,4R*),4 alpha]-7-[3-(3-hydroxy-4-phenyl-1-pentenyl)-7- oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (4), was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Alcohol 4 was the only member in a series of allylic alcohols which did not display direct contractile activity in the rat stomach strip model. Alcohol 4 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-rich plasma (I50 = 0.65 +/- 0.1 microM); (b) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (pA2 = 8.0 +/- 0.2) or rat aorta (pA2 = 8.1 +/- 0.2); and (c) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (1 mg/kg iv). A radioiodinated analogue of 4 bound in a specific and saturable manner to human platelet membranes with a Kd = 2.3 +/- 0.9 nM. Modification of the alpha-chain, in an attempt to minimize in vivo metabolism, resulted in TxA2 receptor antagonists of reduced in vitro potency.

  DOI：

  10.1021/jm00168a032
• 作为产物：
  描述：

  methyl 2-<(4-tert-butyldimethylsilyloxy)phenyl>propionate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 生成 dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate
  参考文献：
  名称：

  9,11-Epoxy-9-homoprosta-5-enoic acid analogs as thromboxane A2 receptor antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha, 2 alpha(Z),3 alpha(1E,3S*,4R*),4 alpha]-7-[3-(3-hydroxy-4-phenyl-1-pentenyl)-7- oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (4), was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Alcohol 4 was the only member in a series of allylic alcohols which did not display direct contractile activity in the rat stomach strip model. Alcohol 4 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-rich plasma (I50 = 0.65 +/- 0.1 microM); (b) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (pA2 = 8.0 +/- 0.2) or rat aorta (pA2 = 8.1 +/- 0.2); and (c) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (1 mg/kg iv). A radioiodinated analogue of 4 bound in a specific and saturable manner to human platelet membranes with a Kd = 2.3 +/- 0.9 nM. Modification of the alpha-chain, in an attempt to minimize in vivo metabolism, resulted in TxA2 receptor antagonists of reduced in vitro potency.

  DOI：

  10.1021/jm00168a032

文献信息

• DAS, JAGABANDHU;HALL, STEVEN E.;NAKANE, MASAMI;HASLANGER, MARTIN F.;REID,+, J. MED. CHEM., 33,(1990) N, C. 1741-1748
  作者：DAS, JAGABANDHU、HALL, STEVEN E.、NAKANE, MASAMI、HASLANGER, MARTIN F.、REID,+

  DOI：——

  日期：——
• ——
  作者：HALL STEVEN E.

  DOI：——

  日期：——
• 9,11-Epoxy-9-homoprosta-5-enoic acid analogs as thromboxane A2 receptor antagonists
  作者：Jagabandhu Das、Steven E. Hall、Masami Nakane、Martin F. Haslanger、Joyce A. Reid、Dianne Garber、Vu Chi Truc、Don N. Harris、Anders Hedberg、Martin L. Ogletree

  DOI：10.1021/jm00168a032

  日期：1990.6

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha, 2 alpha(Z),3 alpha(1E,3S*,4R*),4 alpha]-7-[3-(3-hydroxy-4-phenyl-1-pentenyl)-7- oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (4), was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Alcohol 4 was the only member in a series of allylic alcohols which did not display direct contractile activity in the rat stomach strip model. Alcohol 4 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-rich plasma (I50 = 0.65 +/- 0.1 microM); (b) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (pA2 = 8.0 +/- 0.2) or rat aorta (pA2 = 8.1 +/- 0.2); and (c) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (1 mg/kg iv). A radioiodinated analogue of 4 bound in a specific and saturable manner to human platelet membranes with a Kd = 2.3 +/- 0.9 nM. Modification of the alpha-chain, in an attempt to minimize in vivo metabolism, resulted in TxA2 receptor antagonists of reduced in vitro potency.