trans-(O,O-diethyl)-2-(tert-butyl)ethenylphosphonate | 75924-69-5

• 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: trans-(O,O-diethyl)-2-(tert-butyl)ethenylphosphonate
• 英文别名: diethyl (E)-(3,3-dimethylbut-1-en-1-yl)phosphonate；(E)-1-diethoxyphosphoryl-3,3-dimethylbut-1-ene
• CAS: 75924-69-5
• 化学式: C₁₀H₂₁O₃P
• 分子量: 220.249
• InChiKey: NEAGKPIPOGMNRR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-(O,O-diethyl)-2-(tert-butyl)ethenylphosphonate 、 (S)-(+)-2-methoxymethyl-1-(1-methylethylideneamino)pyrrolidine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 {2-tert-Butyl-4-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-pentyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  Enders, Dieter; Wahl, Heiner; Papadopoulos, Kyriakos, Liebigs Annalen, 1995, # 7, p. 1177 - 1184

  摘要：

  DOI：
• 作为产物：
  描述：

  亚磷酸二乙酯钾盐 、 [(E)-3,3-二甲基-1-丁烯基]氯化汞 以 二甲基亚砜 为溶剂， 反应 29.0h， 以76%的产率得到trans-(O,O-diethyl)-2-(tert-butyl)ethenylphosphonate
  参考文献：
  名称：

  Substitution reactions of vinylmercurials by a free-radical chain mechanism

  摘要：

  DOI：

  10.1021/ja00545a054

文献信息

• Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Schöllkopf's Bislactim Ethers to Vinylphosphonates
  作者：María Ruiz、M. Carmen Fernández、Aniana Díaz、José M. Quintela、Vicente Ojea

  DOI：10.1021/jo034707q

  日期：2003.10.1

  Conjugate additions of lithiated bislactim ethers derived from cyclo-[Gly-Val] and cyclo-[Ala-Val] to alpha-, beta-, or alpha,beta-substituted vinylphosphonates allow direct and stereoselective access to a variety of 3- or 4-monosubstituted and 2,3-, 2,4-, or 3,4-disubstituted 2-amino-4-phosphonobutanoic acids (AP4 derivatives) in enantiomerically pure form. The relative stereochemistry was assigned

  将衍生自环-[Gly-Val]和环-[Ala-Val]的锂化双lactimin醚与α-，β-或α，β-取代的乙烯基膦酸酯共轭加成可直接和立体选择性地获得各种3-或4对映体纯形式的-单取代和2,3-，2,4-或3,4-二取代的2-氨基-4-膦酰基丁酸（AP4衍生物）。通过X-射线衍射分析或1，2-氧杂磷杂环丁烷衍生物的NMR研究确定相对立体化学。调用竞争性的八元“紧凑”和“松弛”过渡态结构以合理化共轭添加物的立体化学结果。
• A new version of the Peterson olefination using bis(trimethylsilyl)methyl derivatives and fluoride ion as catalyst
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. Garcia、Inaki Ganboa、F. P. Cossio、Begona Lecea、Concepcion Lopez

  DOI：10.1021/jo00295a047

  日期：1990.4
• Hydrophosphorylation of Terminal Alkynes Catalyzed by Palladium
  作者：N. S. Gulykina、T. M. Dolgina、G. N. Bondarenko、I. P. Beletskaya

  DOI：10.1023/b:rujo.0000003155.15312.f4

  日期：2003.6

  A series of new 1-aryl-, 1-heteroaryl-, and 1-alkylethenylphosphonates was prepared by hydrophosphorylation of terminal acetylenes catalyzed by palladium. A stable in air complex Pd-2(dba)(3) (.) CHCl3 was applied as catalyst. The reaction mechanism is discussed.
• Diastereo- and enantioselective synthesis of 2,3- and 1,2-disubstituted 4-oxophosphonates via asymmetric Michael addition
  作者：Dieter Enders、Heiner Wahl、Kyriakos Papadopoulos

  DOI：10.1016/s0040-4020(97)00814-4

  日期：1997.9

  Asymmetric Michael addition of lithiated SAMP hydrazones (S)-2 to a variety of alkenylphosphonates (E)-3 followed by oxidative cleavage of the 1,4-adducts 4 afforded 2,3-disubstituted 4-oxophosphonates 5 with good to very good yields (58-80%), low to moderate diastereomeric (de = 6-74%) and excellent enantiomeric excesses (ee = >93%). Pure anti-diastereomers (ee = >93%) of 5 were obtained by separation of the stereoisomers by HPLC. In addition, the lithiated SAMP hydrazone (S)-2a was added to alkenylphosphonates (E)-3, and the lithio phosphonate anions were trapped with alkyl halides or sulfates, yielding 1,2-disubstituted 4-oxophosphonates 8 with moderate to good yields (38-69%), low to good diastereomeric (de = 10-77%) and high enantiomeric excesses (ee = >90%) after oxidative cleavage. (C) 1997 Elsevier Science Ltd.
• PALOMO, CLAUDIO;AIZPURUA, JESUS M.;GARCIA, JESUS M.;GANBOA, INAKI;COSSIO,+, J. ORG. CHEM., 55,(1990) N, C. 2498-2503
  作者：PALOMO, CLAUDIO、AIZPURUA, JESUS M.、GARCIA, JESUS M.、GANBOA, INAKI、COSSIO,+

  DOI：——

  日期：——