triphenylcinnamylphosphonium bromide | 32347-06-1

• 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: triphenylcinnamylphosphonium bromide
• 英文别名: trans-β-Styryl-triphenyl-phosphonium-bromid；(E)-Styryltriphenylphosphonium；(trans-PhCH=CHPPh3)Br；Triphenyl[(E)-2-phenylethenyl]phosphanium bromide；triphenyl-[(E)-2-phenylethenyl]phosphanium;bromide
• CAS: 32347-06-1
• 化学式: Br*C₂₆H₂₂P
• 分子量: 445.338
• InChiKey: SOEMJAMNYHUTBK-QUABFQRHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  28
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triphenylcinnamylphosphonium bromide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (1,2-diphenylethyl)diphenylphosphine oxide
  参考文献：
  名称：

  膦与乙炔的反应。第十二部分。α-不饱和phospho盐和“维蒂希型” phospho甜菜碱常见的1,2-芳基迁移机理

  摘要：

  （a）亚甲基三苯基膦与酒精中的苯甲醛，（b）三芳基膦与苯乙烯中的氧化苯乙烯的反应，以及（c）三芳基膦与亲电乙炔和水的反应，以及（d）αβ-不饱和phospho盐的碱性水解，都涉及形成甜菜碱，羟乙基phosph盐，αβ-不饱和氢氧化hydroxide和相应的五共价氧磷烷的平衡混合物。在温和的碱性条件下，产物主要来自于乙烯基催化的膦氧烷的碱催化重排，但在更碱性的条件下，甜菜碱的分解占主导地位。

  DOI：

  10.1039/j39710001059
• 作为产物：
  描述：

  [(Z)-2-溴乙烯基]苯 、 三苯基膦 以 苯 为溶剂， 反应 24.0h， 生成 triphenylcinnamylphosphonium bromide
  参考文献：
  名称：

  全反式-1,6-二苯基-1,3,5-己三烯的光异构化。温度和氘同位素效应†

  摘要：

  辐照乙腈 (AN) 中的全反式 1,6-二苯基-1,3,5-己三烯 (ttt-DPH) 通过相对低效的途径但主要通过单重激发态产生 ctt-和 tct-DPH。假设...

  DOI：

  10.1021/jp021540g

文献信息

• Synthesis of η²-Phosphonioalkene−Palladium(0) Complexes from Alkenylphosphonium Halides and Palladium(0) Species. Structure and Substitution Reactions of These Complexes
  作者：Jiun-Pey Duan、Fen-Ling Liao、Sue-Lein Wang、Chien-Hong Cheng

  DOI：10.1021/om961043k

  日期：1997.9.1

  Treatment of trans-[R1CHCR2(PPh3)]+Br- with Pd(dba)2 in the presence of 1 equiv of PPh3 or P(OPh)3 gave the corresponding palladium complexes Pd[trans-R1CHCR2(PPh3)](L)Br (L = PPh3, R1 = Ph, R2 = H (3). L = PPh3, R1 = Me, R2 = H (7); R1 = CO2Et, R2 = H (8); R1 = CO2Me, R2 = H (9); R1 = H, R2 = Me (10). L = P(OPh)3, R1 = CO2Me, R2 = H (11)) in 54−92% yields. Substitution studies showed complexes 3 and 9

  加入Pd（DBA）的治疗2（DBA =苄基丙酮）与（反式-RCH CHPPh 3）+溴-二氯甲烷中，得到[钯（反式-RCH CHPPh 3）2 BR] +（R = CO 2的Et（4），CO 2 Me（5），Ph（6））。如X射线衍射的结果所示，4采用扭曲的五边形几何结构，具有两个EtO 2 CCH CH（PPh 3）+部分和一个溴化物配体。EtO 2 CCH CH（PPh 3）+部分中的C-C双键与钯（0）中心π键结合，并与溴化物配体和金属中心共面。两个（EtO 2 CCH CHPPh 3）+部分均被定向，两个PPh 3基团彼此反式，连接到PPh 3上的烯烃碳占据了邻近溴化物配体的配位点。的治疗反式- [R 1 CH CR 2（PPH 3）] +溴-用Pd（DBA）2在1当量的PPh 3或P（OPh）3存在下，得到相应的钯配合物Pd [反式-R 1 CH CR 2（PPh 3）]（L）Br（L
• Synthesis and Structure of η²-Phosphonioalkene−Palladium(0) Complexes. A Catalyst Intermediate in the Palladium-Mediated Synthesis of Alkenylphosphonium Halides
  作者：Chien-Chih Huang、Jiun-Pey Duan、Ming-Yuan Wu、Fen-Ling Liao、Sue-Lein Wang、Chien-Hong Cheng

  DOI：10.1021/om970709n

  日期：1998.2.1

  Treatment of Pd(PPh3)(4) with PhCH=CHBr in THF at 45 degrees C gave [(trans-PhCH=CHPPh3)Pd(PPh3)(2)]Br-+(-) (1), which was found to be converted from Pd(PPh3)(2)(CH=CHPh)Br. X-ray structural analysis shows that 1 adopts a distorted-square-planar geometry with two PPh3 ligands and a (PhCH=CHPPh3)(+) moiety. The C-C double bond in the latter is pi-bonded to the palladium(0) center and occupies two of the four square-planar coordination sites. Under similar reaction conditions, Pd[P-trans-PhCH=CHP(p-tolyl)(3)][P(p-tolyl)(3)](2)}Br-+(-) (2) was formed from Pd[P(p-tolyl)(3)](4) and PhCH=CHBr, while [(trans-MeCH=CHPPh3)Pd(PPh3)(2)]Br-+(-) (3) was isolated from the reactions of Pd(PPh3)4 with MeCH=CHBr. Treating PhCH=CHBr with trans-Pd(PPh3)(2)(C6H4O-p-CH3)I in THF at ambient temperature led to the formation of (trans-PhCH=CHPPh3)Pd(PPh3)X (5) and (p-CH3OC6H4PPh3)X-+(-) (X, mixture of Br and I). Complex 5 (X Br) can be prepared by treating trans-PhCH=CH(PPh3)Br-+(-) with Pd(dba)(2) and 1 equiv of PPh3 in CH2Cl2. X-ray analysis shows 5 adopts a distorted-square-planar structure consisting of PPh3, X, and PhCH=CH(PPh3)(+) as ligands. The PPh3 ligand is trans to the olefin carbon that is connected to the PPh3 group in PhCH=CH(PPh3)(+), while the halide ligand is trans to the olefin carbon bonded to a phenyl moiety. Reaction of 5 (X = Br) with 1 equiv of PPh3 at ambient temperature afforded 1 in high yield. Pd(PPh3)(4) or Pd(OAc)(2) catalyzes the reactions of PPh3 with PhCH=CHBr, MeCH=CHBr, MeCH=C(Me)Br (mixtures of isomers), CH2=C(Me)Br, cis-(EtO2C)CH=CHBr, and cis-(MeO2C)CH=CHBr to give the corresponding trans-RCH=CR'(PPh3)Br-+(-). During the reaction of PPh3 with PhCH-CHBr, 1 was found to be a catalyst intermediate in the reaction solution. All the pho sphonioalkene-palladium(0) complexes and alkenylphosphonium halides isolated are trans in the (RCH-CR'PPh3)(+) moiety.
• [EN] SMALL MOLECULE HSP70 INHIBITORS<br/>[FR] INHIBITEURS DE HSP70 À PETITE MOLÉCULE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2015130922A2

  公开（公告）日：2015-09-03

  In an effort to discover therapies for treating HSP70 related diseases, a previously unidentified hydrophobic pocket was found in the C-terminal domain of DnaK and of human HSP70. A novel chemical scaffold was also discovered for identifying compounds that treat diseases related to this hydrophobic pocket. The compounds have the structure of formula (I), wherein L, M, and R1-R5 are defined herein and are, therefore, in these therapies, optionally with other pharmaceutical agents such as genotoxic agents. Accordingly these compounds are useful in inhibiting HSP70 or DnaK, reducing HSP70 in mitochondria of a cancer cell, treating malignant neoplastic disease, or inhibiting or reducing bacterial growth. These compounds also resulted in novel methods of screening for a HSP70 inhibitor or DnaK inhibitor by using the three-dimensional structure of the hydrophobic pocket in DnaK or HSP70.
• Reactions of phosphines with acetylenes. Part XII. The mechanisms of 1,2-aryl migrations common to αβ-unsaturated phosphonium salts and “Wittig-type” phosphonium betaines
  作者：Eileen M. Richards、John C. Tebby

  DOI：10.1039/j39710001059

  日期：——

  The reactions of (a) methylenetriphenylphosphorane with benzaldehyde in alcohol, (b) triarylphosphines with styrene oxide in alcohol, and (c) triarylphosphines with electrophilic acetylenes and water, and (d) the alkaline hydrolysis of αβ-unsaturated phosphonium salts, all involve the formation of an equilibrium mixture of a betaine, a hydroxyethylphosphonium salt, an αβ-unsaturated phosphonium hydroxide

  （a）亚甲基三苯基膦与酒精中的苯甲醛，（b）三芳基膦与苯乙烯中的氧化苯乙烯的反应，以及（c）三芳基膦与亲电乙炔和水的反应，以及（d）αβ-不饱和phospho盐的碱性水解，都涉及形成甜菜碱，羟乙基phosph盐，αβ-不饱和氢氧化hydroxide和相应的五共价氧磷烷的平衡混合物。在温和的碱性条件下，产物主要来自于乙烯基催化的膦氧烷的碱催化重排，但在更碱性的条件下，甜菜碱的分解占主导地位。
• Photoisomerization of all-<i>trans</i>-1,6-Diphenyl-1,3,5-hexatriene. Temperature and Deuterium Isotope Effects
  作者：Jack Saltiel、Govindarajan Krishnamoorthy、Zhennian Huang、Dong-Hoon Ko、Shujun Wang

  DOI：10.1021/jp021540g

  日期：2003.5.1

  Irradiation of all-trans-1,6-diphenyl-1,3,5-hexatriene (ttt-DPH) in acetonitrile (AN) gives ctt- and tct-DPH by relatively inefficient pathways but mainly via the singlet excited state. Assuming th...

  辐照乙腈 (AN) 中的全反式 1,6-二苯基-1,3,5-己三烯 (ttt-DPH) 通过相对低效的途径但主要通过单重激发态产生 ctt-和 tct-DPH。假设...