diethyl 1-methyl-n-but-3-enylphosphonate | 71071-59-5

• 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: diethyl 1-methyl-n-but-3-enylphosphonate
• 英文别名: diethyl 2-methyl-3-butenylphosphonate；(1-methyl-but-3-enyl)-phosphonic acid diethyl ester；(1-Methyl-but-2ξ-enyl)-phosphonsaeure-diaethylester；(1-Methyl-but-3-enyl)-phosphonsaeure-diaethylester；4-Diethoxyphosphorylpent-1-ene
• CAS: 71071-59-5
• 化学式: C₉H₁₉O₃P
• 分子量: 206.222
• InChiKey: OADBFUWZIFNIPX-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 0.3 Torr)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  diethyl 1-methyl-n-but-3-enylphosphonate 在 正丁基锂 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 3.5h， 生成 (5-Iodomethyl-3-methyl-2-phenyl-tetrahydro-furan-3-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  t-BuOK-Induced Cleavage of Dihydrofuran Derivatives: Synthesis of .beta.-(Diethoxyphosphinyl)-.beta.,.gamma.-unsaturated Ketones

  摘要：

  DOI：

  10.1021/jo00126a067
• 作为产物：
  描述：

  4-chloropent-2-ene 、 sodium diethyl phosphite 生成 diethyl 1-methyl-n-but-3-enylphosphonate
  参考文献：
  名称：

  Pudowik; Scharipowa, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 589,592;engl.Ausg.S.561,562

  摘要：

  DOI：

文献信息

• The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides
  作者：Jung Hwan Hah、Jun Mo Gil、Dong Young Oh

  DOI：10.1016/s0040-4039(99)01747-5

  日期：1999.11

  1-Alkenylphosphonic acid derivatives of purines have been proven to exhibit significant antiviral activity among these series of compounds. Here we disclose the stereoselective synthesis of the constrained analogs of 1-alkenylphosphonate derivatives of purines via intramolecular epoxide opening reaction of γ,δ-epoxyalkanephosphonates with subsequent Mitsunobu coupling reactions with purine bases.

  嘌呤的1-烯基膦酸衍生物已被证明在这些系列化合物中显示出显着的抗病毒活性。在这里，我们公开了通过γ，δ-环氧烷膦酸酯的分子内环氧化物开环反应以及随后的与嘌呤碱基的Mitsunobu偶联反应的嘌呤的1-烯基膦酸酯衍生物的受约束类似物的立体选择性合成。
• Cycloaddition of Nitrile Oxides to Unsaturated Phosphonates
  作者：Shi Yong Lee、Bum Sung Lee、Chi-Wan Lee、Dong Young Oh

  DOI：10.1080/00397919908085997

  日期：1999.10

  Abstract The 2-isoxazohes and isoxazole functionalized with phosphonate group were synthesized by the 1,3-dipolar cycloaddition reaction of nitrile oxides with various unsaturated phosphonates.

  摘要 通过腈氧化物与各种不饱和膦酸酯的1,3-偶极环加成反应合成了膦酸酯基官能化的2-异恶唑和异恶唑。
• Dephosphonylation of β-Carbonyl Phosphonates
  作者：Shi Yong Lee、Chi-Wan Lee、Dong Young Oh

  DOI：10.1021/jo990221r

  日期：1999.9.1

  A new methodology has been developed for the P-C bond cleavage of beta-carbonyl phosphonates. The alpha,alpha-disubstituted beta-keto phosphonates and the alpha-carbamoyl phosphonates have been shown to undergo dephosphonylation by reaction of their lithium enolate with LiAlH4, followed by quenching with aqueous H2SO4, affording regioselectively alpha,alpha-disubstituted ketone and alpha-substituted and alpha,alpha-disubstituted secondary amides.
• Savignac,P. et al., Synthetic Communications, 1979, vol. 9, p. 487 - 496
  作者：Savignac,P. et al.

  DOI：——

  日期：——
• Studies on the free radical carbon-carbon bond formation in the reaction of α-phosphoryl sulfides and selenides with alkenes
  作者：Piotr Bałczewski、Witold M. Pietrzykowski、Marian Mikołlajczyk

  DOI：10.1016/0040-4020(95)00393-m

  日期：1995.7

  alpha-Mono- and alpha, alpha-disubstituted alpha-phosphoryl radicals 9 were generated from the easy accessible alpha-phosphoryl sulfides 4, 5 and alpha-phosphoryl selenides 11, 12 and reacted with the electron rich alkenes 6 under the reductive (n-Bu(3)SnH/AIBN) conditions to give the functionalized phosphonates 7 in 32 divided by 68% yield. Two fragmentation processes of the phosphonate a-alkoxy alkyl radicals are also described.