(E)-(but-2-en-1-yl)triphenylphosphonium bromide | 39741-81-6

• 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)-(but-2-en-1-yl)triphenylphosphonium bromide
• 英文别名: (E)-buten-2-en-1-yltriphenylphosphonium bromide；(E)-but-2-en-1-yl triphenylphosphonium bromide；(E)-but-2-en-1-yltriphenylphosphonium bromide；crotyl triphenylphosphonium bromide；crotyltriphenylphosphonium bromide；but-2t-enyl-triphenyl-phosphonium; bromide；(E)-2-Butenyltriphenyl-phosphoniumBromide；[(E)-but-2-enyl]-triphenylphosphanium;bromide
• CAS: 39741-81-6
• 化学式: Br*C₂₂H₂₂P
• 分子量: 397.294
• InChiKey: GJDNAYRZYAGDKR-SQQVDAMQSA-M

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  (E)-(but-2-en-1-yl)triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 <(E)-but-2-enylidene>triphenylphosphorane
  参考文献：
  名称：

  Total Synthesis of Natural and ent-Fredericamycin A

  摘要：

  A total synthesis of both enantiomers of the potent antitumor-antibiotic fredericamycin A (1) is detailed based on a room temperature inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene for assemblage of a pyridone F ring precursor, a single-step Michael addition-intramolecular acylation for annulation of the DE ring system onto this pyridone F ring precursor, implementation of a regiospecific chromium carbene benzannulation reaction for AB ring construction, and a simple aldol closure for introduction of the spiro CD ring system. Resolution of the penultimate precursor 41 followed by deprotection provided natural and ent-fredericamycin A. The indistinguishable cytotoxic potency of the two enantiomers (L1210 IC50, 0.03 and 0.04 mu g/mL, respectively) is disclosed along with that of the key partial structures 2 (IC50 = 2 mu g/mL) and 21 IC50 = 7 mu g/mL) constituting the fully functionalized ABCDE and DEF ring systems of the natural product.

  DOI：

  10.1021/ja00153a004
• 作为产物：
  描述：

  1-溴-2-丁烯 、 三苯基膦 反应 12.0h， 以90%的产率得到(E)-(but-2-en-1-yl)triphenylphosphonium bromide
  参考文献：
  名称：

  Novel Methodology for the Preparation of Five-, Seven-, and Nine-Membered Fused Rings on C₆₀

  摘要：

  The photocycloaddition of dienyl cyclopropanes to C-60 gives a new synthetic approach to yield stereospecifically five-, seven-, and nine-membered [60]fullerene adducts. Our results suggest the formation of a biradical intermediate between the dienyl substrate and C-60. An electron transfer between the triplet excited state of C-60 and the dienyl substrate precedes the formation of the intermediate.

  DOI：

  10.1021/ol0600887

文献信息

• 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。
• Stereoselective Syntheses of the Isomeric 5, 10-Pentadecadienals
  作者：Günther Ohloff、Christian Vial、Ferdinand Näf、Manfred Pawlak

  DOI：10.1002/hlca.19770600404

  日期：1977.6.1

  The four isomeric 5, 10-pentadecadienals 1, 2, 3 and 4 were prepared by stereo-selective routes from acetylenic precursors. Two of them, 2 and 4, were also made by Wittig reaction from 2-hydroxytetrahydropyran (29). 2-Hydroxytetrahydropyran (29) yields (Z)-5-alkenols efficiently by Wittig reaction, and (Z)-4-hexenol was similarly made from 2-hydroxytetrahydrofuran (66).

  四个异构体5,10-pentadecadienals 1，2，3和4是由从炔属前体立体选择性途径制备。它们中的两个2和4也是由Wittig反应由2-羟基四氢吡喃制成的（29）。2-羟基四氢吡喃（29）通过Wittig反应有效地产生（Z） -5-烯醇，（Z） -4-己烯醇类似地由2-羟基四氢呋喃（66）制成。
• Pheromone XXXIV. Synthese konjugiert-ungesättigter Lepidopterenpheromone und Analoga
  作者：Hans Jürgen Bestmann、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119811205

  日期：1981.12.24

  Nach Art eines “Baukastensystems” werden konjugiert-ungesättigte Alkadienylacetate, Alkadienole und Alkadienale, wie sie als Sexualpheromone weiblicher Schmetterlinge bekannt sind, mit unterschiedlichen Positionen und Geometrien der Doppelbindungen synthetisiert.

  以“模块系统”的方式，合成了共轭-不饱和乙酸链二烯基乙酸酯，链二烯醇和链二烯醛，它们被称为雌性蝴蝶的性信息素，其双键的位置和几何结构不同。
• Collective total synthesis of botryanes
  作者：Chuang Qiao、Wen Zhang、Jing-Chun Han、Wei-Min Dai、Chuang-Chuang Li

  DOI：10.1016/j.tet.2018.11.019

  日期：2019.3

  total synthesis of a series of botryanes, which are an important group of sesquiterpene antibiotics isolated from the metabolites of the fungus Botrytis cinerea, has been reported. The highly functionalized hydrindane skeleton of the botryanes was efficiently synthesized via an unusual intramolecular Diels-Alder reaction, which was promoted by TsOH as a protic acid. The concise total synthesis of (±)-hypocrolide

  已经报道了一系列硼烷的集体全合成，所述硼烷是从灰葡萄孢菌的代谢物中分离出的重要的倍半萜类抗生素。通过不寻常的分子内Diels-Alder反应有效地合成了硼烷的高度官能化的氢化茚骨架，该反应由TsOH作为质子酸促进。从容易获得的起始原料开始，只需8个步骤即可完成具有挑战性的六环骨架的（±）-次大环内酯A的简明全合成。
• METHODS OF DESIGNING, PREPARING, AND USING NOVEL PROTONOPHORES
  申请人：Martineau Louis C.

  公开号：US20140135359A1

  公开（公告）日：2014-05-15

  The present invention provides a computer-assisted method of generating a protonophore requiring the use of a computer including a processor. The method includes: designing the protonophore, calculating, using the processor, an estimated protonophoric activity; producing the protonophore if the estimated protonophoric activity corresponds to an U 50 of about 20 μM or less; and determining the uncoupling activity of the protonophore. The present invention also provides novel protonophores that meet the above requirement and their methods of use.

  本发明提供了一种利用计算机辅助的方法来生成需要使用处理器的质子载体。该方法包括：设计质子载体，使用处理器计算估计的质子载体活性；如果估计的质子载体活性对应于大约20微米或更少的U50，则生产质子载体；并确定质子载体的解耦活性。本发明还提供了符合上述要求的新型质子载体及其使用方法。