(E)-cinnamyltriphenylphosphonium bromide | 38633-40-8

• 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: (E)-cinnamyltriphenylphosphonium bromide
• 英文别名: [(E)-3-phenylprop-2-enyl]triphenylphosphonium bromide；(cinnamyl)(triphenyl)phosphonium bromide；cinnamyl triphenylphosphonium bromide；cinnamyltriphenylphosphonium bromide；(cinnamyl)triphenylphosphonium bromide；trans-cinnamyl-triphenyl-phosphonium; bromide；triphenyl-[(E)-3-phenylprop-2-enyl]phosphanium;bromide
• CAS: 38633-40-8
• 化学式: Br*C₂₇H₂₄P
• 分子量: 459.365
• InChiKey: APIBROGXENTUGB-ZUQRMPMESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (E)-cinnamyltriphenylphosphonium bromide 在 乙醇锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 (E)-3,4-diphenylstilbene
  参考文献：
  名称：

  Utilization of the 1,4-conjugated Wittig reaction for the synthesis of substituted 1,3-cyclohexadines

  摘要：

  DOI：

  10.1021/jo00923a038
• 作为产物：
  描述：

  反式肉桂醛 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 乙醚 、 苯 为溶剂， 反应 7.0h， 生成 (E)-cinnamyltriphenylphosphonium bromide
  参考文献：
  名称：

  Courtot,P. et al., Bulletin de la Societe Chimique de France, 1977, p. 749 - 757

  摘要：

  DOI：

文献信息

• Synthesis and Characterization of New Heptalenes with Extended<i>π</i>-Systems Attached to Them
  作者：Sarah Maillefer-El Houar、Peter Uebelhart、Anthony Linden、Hans-Jürgen Hansen

  DOI：10.1002/hlca.201300137

  日期：2013.8

  displayed in Scheme 3, and the thus obtained methyl heptalene‐5‐carboxylates of type A and B are listed in Table 1. The CC bonds of the 2‐arylethenyl and 4‐arylbuta‐1,3‐dien‐1‐yl groups of π(1) and π(2) were in all cases (E)‐configured and showed s‐trans conformation at the CC bonds (X‐ray and 1H‐NOE evidence) in the B‐type as well as in the A‐type heptalenes (cf. Figs. 5–12).

  型的甲基heptalenecarboxylates阿和乙与π（1）和π（2）的1,4-二关系（取代基方案1）中synthetized开始用二甲基-1- methylheptalene -4,5-二羧酸5B和6B从7-异丙衍生-1,4-二甲基az（=愈创木z）和1,4,6,8-四甲基az与乙酰二羧酸二甲酯发生热反应。流程3显示了引入π（1）和π（2）取代基的另一种通用方法，由此获得的A和B型甲基庚烯-5-羧酸酯中列出表1的2-arylethenyl和4- arylbuta -1,3-二烯-1-基团的CC键π（1）和π（2）在所有情况下（É）构型并在B型以及A型庚二烯中在CC键（X射线和1 H-NOE证据）处显示了反式构象（参见图5-12）。
• Structure-Based Design, Synthesis, and A-Site rRNA Cocrystal Complexes of Functionally Novel Aminoglycoside Antibiotics:  C2‘ ‘ Ether Analogues of Paromomycin
  作者：Stephen Hanessian、Janek Szychowski、Susanta Sekhar Adhikari、Guillermo Vasquez、Pachamuthu Kandasamy、Eric E. Swayze、Michael T. Migawa、Ray Ranken、Boris François、Julia Wirmer-Bartoschek、Jiro Kondo、Eric Westhof

  DOI：10.1021/jm061200+

  日期：2007.5.1

  A series of 2"-O-substituted ether analogues of paromomycin were prepared based on new site-selective functionalizations. X-ray cocrystal complexes of several such analogues revealed a new mode of binding in the A-site rRNA, whereby rings I and II adopted the familiar orientation and position previously observed with paromomycin, but rings III and IV were oriented differently. With few exceptions,

  根据新的位点选择性功能化，制备了一系列2'-O-取代的巴龙霉素醚类似物。几种类似物的X射线共晶复合物揭示了在A位rRNA中的新结合方式，即环I和II采用了以前对巴龙霉素观察到的熟悉的方向和位置，但环III和IV的取向不同，除少数例外，所有这些新类似物对敏感的金黄色葡萄球菌均表现出与巴龙霉素相同或更好的抑制活性。获得了针对大肠杆菌的MIC值，其中一些醚附件含有极性或碱性端基；两种类似物在小鼠败血病保护试验中显示出优异的存活率；对肾脏的初步组织病理学分析未显示明显的毒性迹象，而使用新霉素和卡那霉素的对照组在较低剂量下有毒。
• A Convenient Method for the Preparation of Conjugated Olefins from Allylic Acetates and Aldehydes. Synthesis of Pellitorine
  作者：Yuhko Tsukahara、Hideki Kinoshita、Katsuhiko Inomata、Hiroshi Kotake

  DOI：10.1246/bcsj.57.3013

  日期：1984.10

  A variety of allylic acetates were treated with sodium bromide and triphenylphosphine in the presence of 5 mol% of [Pd(PPh3)4] to give the phosphonium salts, which were converted to the ylids in situ and allowed to react with various aldehydes to afford the corresponding conjugated olefins in good yields. Furthermore, this procedure was applied to the synthesis of an insecticidal substance, Pellitorine

  在 5 mol% [Pd(PPh3)4] 存在下用溴化钠和三苯基膦处理各种烯丙基乙酸酯，得到鏻盐，将其原位转化为叶立德，并与各种醛反应得到相应的共轭烯烃收率良好。此外，该程序还用于合成杀虫物质 Pellitorine。
• Intramolecular reactions of α-azidocinnamates with 4-substituted 1,3-dienes
  作者：Claus Vogel、Paul Delavier、Peter G. Jones、Detlev Döring

  DOI：10.1016/0040-4039(91)80343-5

  日期：1991.3

  The syntehsis of new 8,9-benzo-6-aza-bicyclo[3.2.2]nona-3,6,8-trienes 14 by intramolecular reaction of α-azidocinnamates 9 with alkyl- and phenylsubstituted ortho-butadienyl side chains is reported, as is the formation of the new 1-aza-2-carbomethoxy-7,8-benzo-tricyclo[4.30.02,9]nona-4,7-diene 15.

  据报道，新的8,9-苯并-6-氮杂双环[3.2.2] nona-3,6,8-三烯14通过分子内的α-叠氮吲哚9与烷基和苯基取代的邻丁二烯基侧链反应合成，以及新的1-氮杂-2-碳甲氧基-7,8-苯并三环[4.30.0 2,9 ]壬娜-4,7-二烯15的形成。
• Highly dichroic benzo-2,1,3-thiadiazoledyes containing five linearly π-conjugated aromatic residues, with fluorescent emission ranging from green to red, in a liquid crystal guest–host system
  作者：Xuelong Zhang、Rumiko Yamaguchi、Keiichi Moriyama、Masami Kadowaki、Takako Kobayashi、Tsutomu Ishi-i、Thies Thiemann、Shuntaro Mataka

  DOI：10.1039/b512493j

  日期：——

  A number of fluorescent benzothiadiazole dyes have been synthesised and their optical properties, when dispersed in a liquid crystal host phase, examined. These dyes have five linearly π-conjugated aromatic ring systems (both with and without ethene and 1,3-butadiene spacers). The liquid crystalline host medium, used was the nematic phase of MLC-2039. The emission colours observed ranged from green to red, depending on the unsaturated chains attached at the 4- and 7- positions of the bezo-2,1,3-thiadiazole core. A highly dichroic and efficient fluoresence was observed. The dye 4,7–bis[5-bis(phenylethenyl)thiophen-2-yl]-2,1,3-benzothiadiazole is of particular importance. This is the first example of a dye emitting strong red fluorescence (633 nm). When dispersed in MLC-2039, dichroic ratio values up to 12.3 were obtained.

  合成了一系列荧光苯并噻二唑染料，并在液晶主体相中分散时研究了它们的光学性质。这些染料具有五个线性π-共轭芳香环系统（包括带有和不带有亚乙烯基和1,3-丁二烯间隔基的情况）。所用的液晶主体介质是MLC-2039的向列相。观测到的发射颜色从绿色到红色不等，具体取决于连接在苯并-2,1,3-噻二唑核心的4-和7-位上的不饱和链。观察到高度二色性和高效的荧光。特别重要的是染料4,7-双[5-双(苯乙烯基)噻吩-2-基]-2,1,3-苯并噻二唑。这是首个发射强烈红色荧光（633 nm）的染料例子。在MLC-2039中分散时，得到了高达12.3的二色比值。