Triphenylphosphin-(brombenzoyl-methylen) | 3201-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Triphenylphosphin-(brombenzoyl-methylen)
• 英文别名: Benzoyl(triphenylphosphoranylidene)methyl bromide；2-bromo-1-phenyl-2-(triphenyl-λ5-phosphanylidene)ethanone
• CAS: 3201-60-3
• 化学式: C₂₆H₂₀BrOP
• 分子量: 459.322
• InChiKey: ZNRGONUTKDLPOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Triphenylphosphin-(brombenzoyl-methylen) 800.0 ℃ 、0.13 Pa 条件下， 以48%的产率得到苯基溴乙炔
  参考文献：
  名称：

  Braga, Antoenio L.; Comasseto, Joaeo V., Synthetic Communications, 1989, vol. 19, # 16, p. 2877 - 2884

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰基亚甲基三苯基膦 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到Triphenylphosphin-(brombenzoyl-methylen)
  参考文献：
  名称：

  通过 Wittig 反应立体选择性合成 α-溴-α,β-不饱和酮

  摘要：

  摘要 首次报道了α-溴苯甲酰基亚甲基三苯基膦2的合成，α-溴叶立德2具有足够的活性进行Wittig反应，为立体选择性合成α-溴-α,β-不饱和酮5提供了一种新方法。

  DOI：

  10.1081/scc-120016319
• 作为试剂：
  描述：

  3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,3-dihydrofuran-5-yl]-2,6-dioxopyrimidine-4-carbaldehyde 在 Triphenylphosphin-(brombenzoyl-methylen) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以13.8%的产率得到1-[3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pento-1-enofuranosyl]uracil
  参考文献：
  名称：

  Vinyl Radical-Based Cyclization of 6-Substituted 1-(2-Deoxy-D-erythro-pent-1-enofuranosyl)uracils: Synthesis of Anomeric Spiro Nucleosides

  摘要：

  The preparation of 6-bromovinyl derivatives,of 1-(2-deoxy-D-erythro-pent-1-enofuranosyl)uracils (10-13) and their radical-mediated reactions leading to the formation of cyclized products were investigated with the aim of developing a new method for the synthesis of anomeric spiro nucleosides. Treatment of O-2,2'-anhydrouridine 5 with LDA followed by HCO(2)Me gave 1-(2-deoxy-D-erythro-pent-1-enofuranosyl)-6-formyluracil (9). The 6-bromovinyl derivatives 10-13 were prepared by Wittig reaction of 9. Compounds 10, 12, and 13 underwent a vinyl radical-mediated cyclization (Bu(3)SnH/AIBN, in refluxing benzene) preferentially in a 5-exo-trig manner to give 2'-deoxy-6,1'-ethenouridines 14a and 17 and the corresponding a-anomers 15a and 18 with preponderance of the former. The anomeric stereochemistry of these spiro nucleosides was unambiguously determined based on X-ray crystallography and their chemical reactions. Conversion of 14a to 2'-deoxy-6,1'-ethanouridine (26) was also carried out. The present method offers a straightforward synthesis of certain anomeric spiro nucleosides.

  DOI：

  10.1021/jo00092a024

文献信息

• Solventless Wittig Olefination with Fluorinated Benzaldehydes
  作者：Thies Thiemann

  DOI：10.3184/030823407x225464

  日期：2007.6

  Fluorinated benzaldehydes undergo solventless Wittig olefination with stabilised phosphoranes. Even with less reactive, stabilised phosphoranes, such as acetylmethylidenetriphenylphosphorane, the reactions have been found to be exothermic.

  氟化苯甲醛与稳定的正膦进行无溶剂 Wittig 烯化。即使使用反应性较低的稳定正膦，例如乙酰亚甲基三苯基正膦，也发现反应是放热的。
• Stereoselective Synthesis of α-Bromo-α,β-unsaturated Ketones via Wittig Reaction
  作者：Zhizhen Huang、Lei Wang、Xian Huang

  DOI：10.1081/scc-120016319

  日期：2003.1.4

  Abstract The synthesis of α-bromo benzoylmethylene triphenylphosphorane 2 is firstly reported and α-bromo ylide 2 has sufficient activity to undergo Wittig reaction, affording a novel method for the stereoselective synthesis of α-bromo-α,β-unsaturated ketones 5.

  摘要 首次报道了α-溴苯甲酰基亚甲基三苯基膦2的合成，α-溴叶立德2具有足够的活性进行Wittig反应，为立体选择性合成α-溴-α,β-不饱和酮5提供了一种新方法。
• Maerkl,G., Chemische Berichte, 1962, vol. 95, p. 3003 - 3007
  作者：Maerkl,G.

  DOI：——

  日期：——
• Phosphororganische Verbindungen, 7. Mitt.: Über die Oxydation von β-Oxo-alkylenphosphoniumsalzen mit Bleitetraacetat
  作者：E. Zbiral

  DOI：10.1007/bf00905504

  日期：1966.1
• BRAGA, ANTONIO L.;COMASSETO, JOAO V., SYNTH. COMMUN., 19,(1989) N6, C. 2877-2883
  作者：BRAGA, ANTONIO L.、COMASSETO, JOAO V.

  DOI：——

  日期：——