(3-Brom-1-propenyl)phosphonsaeure-diethylester | 95713-71-6

• 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: (3-Brom-1-propenyl)phosphonsaeure-diethylester
• 英文别名: diethyl (3-bromoprop-1-enyl)phosphonate；diethyl 3-bromoprop-1-enylphosphonate；Diethyl 3-bromoprop-1-en-1-ylphosphonate；3-bromo-1-diethoxyphosphorylprop-1-ene
• CAS: 95713-71-6
• 化学式: C₇H₁₄BrO₃P
• 分子量: 257.064
• InChiKey: YTQMZWCJYREOLX-UHFFFAOYSA-N

物化性质

• 沸点：
  289.5±32.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (3-Brom-1-propenyl)phosphonsaeure-diethylester 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 51.0h， 生成 <4-(4-Nitrophenyl)-1,3-butadienyl>phosphonsaeure-diethylester
  参考文献：
  名称：

  Flitsch, Wilhelm; Jerman, Franz, Liebigs Annalen der Chemie, 1985, p. 307 - 311

  摘要：

  DOI：
• 作为产物：
  描述：

  烯丙基磷酸二乙酯 在 溴 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 (3-Brom-1-propenyl)phosphonsaeure-diethylester
  参考文献：
  名称：

  Synthesis of Nitrogen Bridgehead Heterocycles with Phosphonates via a Novel Tandem Process

  摘要：

  A novel and efficient method was developed for the synthesis of nitrogen bridgehead heterocycles with phosphonates. Nitrogen containing five-membered heterocyclic aldehyde and diethyl 3-bromoprop-1-enylphosphonate were used as substrates. Bridgehead nitrogen-containing arylphosphonates were obtained via one-pot reaction including four steps: S(N)2, deprotonation followed by electron flow, nucleophic additon and elimination of water.

  DOI：

  10.3987/com-12-12661

文献信息

• The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs
  作者：Emily R. Jackson、Géraldine San Jose、Robert C. Brothers、Emma K. Edelstein、Zachary Sheldon、Amanda Haymond、Chinchu Johny、Helena I. Boshoff、Robin D. Couch、Cynthia S. Dowd

  DOI：10.1016/j.bmcl.2013.11.067

  日期：2014.1

  nonmevalonate pathway (NMP) of isoprene biosynthesis has been examined as a source of new antibiotics with novel mechanisms of action. Dxr is the best studied of the NMP enzymes and several reports have described potent Dxr inhibitors. Many of these compounds are structurally related to natural products fosmidomycin and FR900098, each bearing retrohydroxamate and phosphonate groups. We synthesized a series of

  对异戊二烯生物合成的非甲羟戊酸途径 (NMP) 的抑制已被研究为具有新作用机制的新抗生素的来源。Dxr 是 NMP 酶中研究得最好的，一些报告描述了有效的 Dxr 抑制剂。许多这些化合物在结构上与天然产物磷酰胺霉素和 FR900098 相关，每个都带有逆异羟肟酸酯和膦酸酯基团。我们合成了一系列具有 2 到 5 个亚甲基单元分隔这些基团的化合物，以检查最佳接头长度并测试对 Mtb Dxr 的抑制。我们合成了这些化合物的乙酯和新戊酸酯，以增加亲脂性并改善对 Mtb 生长的抑制。我们的结果表明丙基或丙烯基接头链是最佳的。丙烯基类似物22具有 IC 50对 Mtb Dxr 为 1.07 μM。22的新戊酰酯化合物26的 MIC 为 9.4 μg/mL，表明此类化合物的抗结核效力显着提高。
• Facile Synthesis of Pyrido[1,2-a]benzimidazole Derivatives via Novel Tandem Reaction Involing Horner-Emmons Reaction
  作者：Jian-Wu Wang、Yan-Qing Ge、Wen-Jing Zhao、Ya-Fei Xie、Wei-Ren Xu、Gui-Long Zhao

  DOI：10.3987/com-13-12712

  日期：——

  Pyrido[1,2-a]benzimidazole derivatives were conveniently synthesized by a novel tandem reaction under mild conditions. The reaction mechanism was also proposed.
• US4182758A
  申请人：——

  公开号：US4182758A

  公开（公告）日：1980-01-08
• US4206156A
  申请人：——

  公开号：US4206156A

  公开（公告）日：1980-06-03
• Synthesis of Nitrogen Bridgehead Heterocycles with Phosphonates via a Novel Tandem Process
  作者：Jian-Wu Wang、Jiong Jia、Ya-Fei Xie、Lei Feng、Hua-Qiang Xu、Song Meng、Gui-Long Zhao、Wei-Ren Xu、Yan-Qing Ge

  DOI：10.3987/com-12-12661

  日期：——

  A novel and efficient method was developed for the synthesis of nitrogen bridgehead heterocycles with phosphonates. Nitrogen containing five-membered heterocyclic aldehyde and diethyl 3-bromoprop-1-enylphosphonate were used as substrates. Bridgehead nitrogen-containing arylphosphonates were obtained via one-pot reaction including four steps: S(N)2, deprotonation followed by electron flow, nucleophic additon and elimination of water.