methyl 3-(diethoxyphosphoryl)bicyclo<1.1.1>pentane-1-carboxylate | 131515-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: methyl 3-(diethoxyphosphoryl)bicyclo<1.1.1>pentane-1-carboxylate
• 英文别名: methyl 3-(diethoxyphosphoryl)bicyclo[1.1.1]pentane-1-carboxylate；Methyl 3-diethoxyphosphorylbicyclo[1.1.1]pentane-1-carboxylate
• CAS: 131515-41-8
• 化学式: C₁₁H₁₉O₅P
• 分子量: 262.243
• InChiKey: DZJKKRKIOHDSJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  methyl 3-(diethoxyphosphoryl)bicyclo<1.1.1>pentane-1-carboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以56%的产率得到diethyl 3-formylbicyclo[1.1.1]pentylphosphonate
  参考文献：
  名称：

  （2S）-和（2R）-2-（3'-膦酰基双环[1.1.1]戊基）甘氨酸作为新型III族选择性代谢型谷氨酸受体配体的合成及生物学评估。

  摘要：

  （2S）-和（2R）-2-（3'-膦酰基双环[1.1.1]戊基）甘氨酸异构体（10和11）的合成，其特征在于2-（3'通过立体选择性Ugi缩合完成膦酸酯部分的-羧基双环[1.1.1]戊-1-基）甘氨酸。测试了这两种异构体对一系列代谢型谷氨酸受体的活性，结果发现S异构体（10）是一种中等效力和选择性的mGluR4激动剂。

  DOI：

  10.1016/j.bmc.2006.01.027
• 作为产物：
  描述：

  3-(甲氧基羰基)二环[1.1.1]戊烷-1-羧酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 methyl 3-(diethoxyphosphoryl)bicyclo<1.1.1>pentane-1-carboxylate
  参考文献：
  名称：

  Synthesis of doubly bridgehead substituted bicyclo[1.1.1]pentanes. Radical transformations of bridgehead halides and carboxylic acids

  摘要：

  Synthetic transformations of the 1-bicyclo[1.1.1]pentyl bridgehead radicals 11 generated from the corresponding bridgehead iodides 3 and carboxylic acids 5 are described. The relatively high nucleophilicity of these radicals was utilized in reactions with carbonyl compounds. In the reaction sequence of preparation of the iodides 3 and their further transformations, [1.1.1]propellane (2) is a synthetic equivalent of the recently described bicyclo[1.1.1]penta-1,3-dienyl dianion (8).

  DOI：

  10.1021/jo00001a058

文献信息

• KASZYNSKI, PIOTR;MCMURDIE, NEIL D.;MICHL, JOSEF, J. ORG. CHEM., 56,(1991) N, C. 307-316
  作者：KASZYNSKI, PIOTR、MCMURDIE, NEIL D.、MICHL, JOSEF

  DOI：——

  日期：——
• Synthesis of doubly bridgehead substituted bicyclo[1.1.1]pentanes. Radical transformations of bridgehead halides and carboxylic acids
  作者：Piotr Kaszynski、Neil D. McMurdie、Josef Michl

  DOI：10.1021/jo00001a058

  日期：1991.1

  Synthetic transformations of the 1-bicyclo[1.1.1]pentyl bridgehead radicals 11 generated from the corresponding bridgehead iodides 3 and carboxylic acids 5 are described. The relatively high nucleophilicity of these radicals was utilized in reactions with carbonyl compounds. In the reaction sequence of preparation of the iodides 3 and their further transformations, [1.1.1]propellane (2) is a synthetic equivalent of the recently described bicyclo[1.1.1]penta-1,3-dienyl dianion (8).
• Synthesis and biological evaluation of (2S)- and (2R)-2-(3′-phosphonobicyclo[1.1.1]pentyl)glycines as novel group III selective metabotropic glutamate receptor ligands
  作者：Rosanna Filosa、Maura Marinozzi、Gabriele Costantino、Mette Brunsgaard Hermit、Christian Thomsen、Roberto Pellicciari

  DOI：10.1016/j.bmc.2006.01.027

  日期：2006.6

  The synthesis of (2S)- and (2R)-2-(3'-phosphonobicyclo[1.1.1]pentyl)glycine isomers (10 and 11), characterized by the bioisosteric replacement of the distal carboxylic group of 2-(3'-carboxybicyclo[1.1.1]pent-1-yl)glycine by the phosphonate moiety, was accomplished by a stereoselective Ugi condensation. The two isomers were tested for their activity against an array of metabotropic glutamate receptors

  （2S）-和（2R）-2-（3'-膦酰基双环[1.1.1]戊基）甘氨酸异构体（10和11）的合成，其特征在于2-（3'通过立体选择性Ugi缩合完成膦酸酯部分的-羧基双环[1.1.1]戊-1-基）甘氨酸。测试了这两种异构体对一系列代谢型谷氨酸受体的活性，结果发现S异构体（10）是一种中等效力和选择性的mGluR4激动剂。