5-diethoxyphosphinoylindan-1-one | 191611-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-diethoxyphosphinoylindan-1-one
• 英文别名: 5-diethoxyphosphoryl-2,3-dihydroinden-1-one
• CAS: 191611-54-8
• 化学式: C₁₃H₁₇O₄P
• 分子量: 268.249
• InChiKey: IOAXFRJGAOHLJI-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±31.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-diethoxyphosphinoylindan-1-one 在 盐酸 、 碳酸氢铵 、 methyloxirane 作用下， 生成 (RS)-1-氨基-5-膦酰基茚满-1-羧酸
  参考文献：
  名称：

  Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists

  摘要：

  The synthesis of two rigidified phenylglycine analogues is disclosed. The cyclic analogue 1 of (R,S)-alpha-methyl-4-phosphonophenylglycine (MPPG) is shown to be a particularly interesting pharmacological tool, for it is a group II selective mGluR antagonist that possesses an inverse agonist-like action

  DOI：

  10.1016/s0960-894x(97)00177-7
• 作为产物：
  描述：

  3-(3-溴苯基)丙酸 在 palladium diacetate 三氯化铝 、 氯化亚砜 、 苄基三乙基氯化铵 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 5-diethoxyphosphinoylindan-1-one
  参考文献：
  名称：

  对谷氨酸受体有活性的化合物的合成：II。茚满系列螺乙内酰脲的合成

  摘要：

  The article describes a general procedure for synthesizing hydantoins of the indan series, which makes it possible to obtain bioisosteric analogs of 1-aminoindan-1,5-dicarboxylic acid, a group I metabotropic glutamate receptor antagonist.

  DOI：

  10.1023/a:1022567630253

文献信息

• Photocatalyst-free visible-light-promoted C(sp²)–P coupling: efficient synthesis of aryl phosphonates
  作者：Shiqi Xiang、Min Li、Zhen Xia、Chen Fang、Wen Yang、Wei Deng、Ze Tan

  DOI：10.1039/d3ob01987j

  日期：——

  A novel and efficient method for the synthesis of aryl phosphonates from aryl halides and trialkylphosphites via EDA complex-based photochemistry has been developed. It is demonstrated that aryl radicals, generated from the photoexcitation of the EDA complex formed by aryl halide and potassium thioacetate, could be intercepted with trialkylphosphite to produce the corresponding aryl phosphonates in

  开发了一种通过基于 EDA 络合物的光化学从芳基卤化物和亚磷酸三烷基酯合成芳基膦酸酯的新颖且有效的方法。结果表明，由芳基卤化物和硫代乙酸钾形成的 EDA 络合物光激发产生的芳基自由基可以用亚磷酸三烷基酯拦截，以中等至良好的收率生成相应的芳基膦酸酯。值得注意的是，该反应在室温下进行，没有任何过渡金属催化剂、氧化剂和光催化剂，表现出高效率、高选择性和操作简单。
• Synthesis, SAR, and X-ray structure of tricyclic compounds as potent FBPase inhibitors
  作者：Tomoharu Tsukada、Mizuki Takahashi、Toshiyasu Takemoto、Osamu Kanno、Takahiro Yamane、Sayako Kawamura、Takahide Nishi

  DOI：10.1016/j.bmcl.2009.08.081

  日期：2009.10

  With the aim of discovering a novel class of fructose-1,6-bisphosphatase (FBPase) inhibitors, a series of compounds based on tricyclic scaffolds was synthesized. Extensive SAR studies led to the finding of 8l with an IC50 value of 0.013 mu M against human FBPase. An X-ray crystallographic study revealed that 8l bound at AMP binding sites of human liver FBPase with hydrogen bonding interactions similar to AMP. (C) 2009 Elsevier Ltd. All rights reserved.
• ——
  作者：E. D. Matveeva、T. A. Podrugina、N. Yu. Morozkina、O. N. Zefirova、I. V. Seregin、S. O. Bachurin、R. Pellicciari、N. S. Zefirov

  DOI：10.1023/a:1022567630253

  日期：——

  The article describes a general procedure for synthesizing hydantoins of the indan series, which makes it possible to obtain bioisosteric analogs of 1-aminoindan-1,5-dicarboxylic acid, a group I metabotropic glutamate receptor antagonist.
• Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists
  作者：Dawei Ma、Hongqi Tian、Hongbin Sun、Alan P. Kozikowshi、Sergey Pshenichkin、Jarda T. Wroblewski

  DOI：10.1016/s0960-894x(97)00177-7

  日期：1997.5

  The synthesis of two rigidified phenylglycine analogues is disclosed. The cyclic analogue 1 of (R,S)-alpha-methyl-4-phosphonophenylglycine (MPPG) is shown to be a particularly interesting pharmacological tool, for it is a group II selective mGluR antagonist that possesses an inverse agonist-like action