dimethyl 1-trimethylsilyloxy 2-propenyl phosphonate | 65220-89-5

• 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: dimethyl 1-trimethylsilyloxy 2-propenyl phosphonate
• 英文别名: Dimethyl 1-(trimethylsilyloxy)-2-propenylphosphonat；Phosphonic acid, [1-[(trimethylsilyl)oxy]-2-propenyl]-, dimethyl ester；1-dimethoxyphosphorylprop-2-enoxy(trimethyl)silane
• CAS: 65220-89-5
• 化学式: C₈H₁₉O₄PSi
• 分子量: 238.296
• InChiKey: FWUGCSLARLFXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 1-trimethylsilyloxy 2-propenyl phosphonate 在 polymer-supported ammonium fluoride: D₃₇₀ 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以100%的产率得到(1-hydroxy-allyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Polymer-Supported Ammonium Fluoride: A Useful Reagent for Si-O Bond Cleavage

  摘要：

  Polymer-supported ammonium fluoride (1) is a convenient reagent for Si-O bond cleavage. Resin 1 is inexpensive, easy to prepare from commercial amine-containing anion exchange resins and aqueous hydrofluoric acid, easy to store. The product is easily separated from the reaction mixture by filtration. The used resins can be regenerated and reused without losing its reactivity.

  DOI：

  10.1080/00397919108021278
• 作为产物：
  描述：

  二甲基三甲硅基膦酸酯 、 丙烯醛 生成 dimethyl 1-trimethylsilyloxy 2-propenyl phosphonate
  参考文献：
  名称：

  混合三价磷-有机硅试剂的羰基插入反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)83802-8

文献信息

• New silicon-phosphorus reagents in organic synthesis. Carbonyl and conjugate addition reactions of silicon phosphite esters and related systems
  作者：David A. Evans、Kenneth M. Hurst、James M. Takacs

  DOI：10.1021/ja00479a031

  日期：1978.5

  1,4-addition reactions of organosilicon tervalent phosphorus esters, XlPOSiR3(X = OMe, NMe2, Ph), with saturated and a,@-unsaturated aldehydes and ketones have been studied. These addition reactions have been compared with the complementary reactions of alkyl phosphorus esters, X2POCH3, and R3SiCI with carbonyl substrates. With a,@-un- saturated aldehydes, a judicious choice of reagent and conditions

  已经研究了有机硅三价磷酯 XlPOSiR3(X = OMe, NMe2, Ph) 与饱和和 a, 不饱和醛和酮的 1,2- 和 1,4- 加成反应。这些加成反应与烷基磷酯、X2POCH3 和 R3SiCI 与羰基底物的互补反应进行了比较。对于α,@-不饱和醛，明智地选择试剂和条件会导致区域选择性1,2-或1,4-加成模式。已经阐明了这些加成反应的一些机理细节。
• A NOVEL SYNTHESIS OF DIALKYL 1-TRIMETHYLSILYLOXY ALLYL PHOSPHONATES
  作者：Zhonghua Li、Chuanfang Zhu

  DOI：10.1080/10426509608029638

  日期：1996.1.1

  Dialkyl 1-trimethylsilyloxy allylphosphonates (3a-3f) were synthesized by a one-pot reaction of trialkyl phosphite (1), carbonyl compounds (2) and trimethylchlorosilane. The procedure was carried out under very mild conditions and was very easy to conduct. The structures of (3) were confirmed by IR, (1)HNMR, P-31 NMR and MS.