bis(trimethylsilyl) 2,3-bis(methoxycarbonyl)propylphosphonite | 676502-30-0

• 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: bis(trimethylsilyl) 2,3-bis(methoxycarbonyl)propylphosphonite
• 英文别名: Bis(trimethylsilyl) 2,3-bis(methoxycarbonyl)-propylphosphonite；dimethyl 2-[bis(trimethylsilyloxy)phosphanylmethyl]butanedioate
• CAS: 676502-30-0
• 化学式: C₁₃H₂₉O₆PSi₂
• 分子量: 368.514
• InChiKey: VELRJOVBKLLOPK-UHFFFAOYSA-N

物化性质

• 沸点：
  126 °C(Press: 1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(trimethylsilyl) 2,3-bis(methoxycarbonyl)propylphosphonite 在 甲醇 、 sodium methylate 作用下， 以 乙醚 为溶剂， 以94%的产率得到sodium 2,3-bis(methoxycarbonyl)propylphosphinate
  参考文献：
  名称：

  功能化丙酸酯及其类似物的新型有机磷取代衍生物的合成

  摘要：

  三价有机磷酸的三甲基甲硅烷基酯与各种官能化丙烯酸酯及其环状类似物的亲核或自由基加成被提议作为在温和条件下合成新的 2-三甲基甲硅烷氧基羰基取代的烷基亚膦酸酯及其衍生物的便捷方法。此外，这些亚膦酸酯的新官能化衍生物，包括氨基、酰胺基和氨基酸片段以及这些化合物的某些性质，作为官能化丙酸酯及其类似物的新型有机磷取代衍生物的重要前体。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:418–428, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20446

  DOI：

  10.1002/hc.20446
• 作为产物：
  描述：

  六甲基二硅氮烷 在 ammonium hypophosphite 作用下， 反应 4.0h， 生成 bis(trimethylsilyl) 2,3-bis(methoxycarbonyl)propylphosphonite
  参考文献：
  名称：

  Synthesis of phosphinic acids on the basis of hypophosphites: VI. General methods for synthesis of pseudo-γ-glutamylpeptides

  摘要：

  A general method for synthesis of 2-substituted pseudo-gamma-glutamylpeptides, namely, [2-(hydroxy-carbonyl)ethyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acids I which are phosphinic acid analogs of,gamma-glutamylpeptides. Bis(trimethylsilyl) hypophosphite (IV) formed from ammonium hypophosphite (II) in situ was added to the respective ck-substituted acrylate to form bis(trimethylsilyl) [2-R-2-(alkoxycarbonyl)ethyl]phosphonites V. Treatment of compounds V in situ with excess dibromoethane followed by alcoholysis gave [2-R-2-( alkoxycarbon),I)ethyl](2-bromoethyl)phosphonic acids VI which without isolation were treated with excess triethyl orthoformate. The sirnultanious esterification and dehydrobrommation led to [2-R-2-( alkoxy-carbonyl)ethyl 1(vinyl)phosphinates III which were isolated and characterized. The Michael addition of diethyl acetamidomalonate to vinylphosphinates III followed by acid hydrolysis of phosphinates VII without their isolation resulted in formation of target [2-R-2-(hydi-oxycai-bonyl)ethyl][')-amino-3-(hydroxycarbonyl)]proyl]phosphinic acids-pseudo-gamma-glutamylpeptides I.

  DOI：

  10.1134/s1070363207050076

文献信息

• A method of synthesis of phosphinic acids on the basis of hypophosphites: VII. Synthesis of pseudo-γ-aminobutanoyl peptides and other phosphinic analogs of γ-aminobutyric acid
  作者：V. V. Ragulin

  DOI：10.1134/s107036320809003x

  日期：2008.9

  A method of synthesis of pseudo-gamma-aminobutanoyl peptides and other phosphinic analogs of gamma-aminobutyric acid from hypophosphites is suggested. Silyl phosphonites formed by in situ addition of bis-(trimethylsilyl) hypophosphite to the corresponding alpha-substituted acrylates, styrene, or vinyl phosphonate used as unsaturated components in the synthesis react in situ with N-(omega-bromoalkyl)phthalimides by an Arbuzov reaction scheme, affording omega-(phthalimido)alkylphosphinic acids possessing beta-substituted beta-(alkoxycarbonyl)ethyl, beta-phenylethyl, or beta-(diethoxyphosphinoyl)ethyl substituents. Acid hydrolysis of these reaction products gives the target aminophosphinic acids: phosphinic analogs of gamma-aminobutyric acid.
• ——
  作者：M. V. Livantsov、A. A. Prishchenko、O. P. Novikova、L. I. Livantsova、E. V. Grigor'ev

  DOI：10.1023/a:1025677628249

  日期：——