[1-(ethoxycarbonyl)butyl]triphenylphosphonium bromide

• 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: [1-(ethoxycarbonyl)butyl]triphenylphosphonium bromide
• 英文别名: (1-ethoxy-1-oxopentan-2-yl)triphenylphosphoniumbromide；phosphorane；(1-Ethoxy-1-oxopentan-2-yl)triphenylphosphonium bromide；(1-ethoxy-1-oxopentan-2-yl)-triphenylphosphanium;bromide
• 化学式: Br*C₂₅H₂₈O₂P
• 分子量: 471.374
• InChiKey: AZLQXUWGRWBERK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-(ethoxycarbonyl)butyl]triphenylphosphonium bromide 在 iron(III) chloride 、 三乙胺 、 palladium dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 77.5h， 生成 4-allyl-3-(n-propyl)-5-(p-methylphenyl)-2(5H)-furanone
  参考文献：
  名称：

  烯丙基溴存在下PdCl2 / FeCl3共催化的2,3-烯丙基酯偶联环的有机铁

  摘要：

  新的偶合：氯化铁与2,3-烯丙基甲酸酯的相互作用产生了2-（5 H）-呋喃基铁物种，据观察该物种很容易与PdCl 2发生金属转移，从而导致与烯丙基溴的偶合（参见方案）。基于该反应，已经开发了一种有效的方法，可以通过使用廉价易得的FeCl 3作为PdCl 2的助催化剂，从容易获得的烯丙基溴和2,3-烯丙基酯合成β-烯丙基多取代的丁烯内酯。

  DOI：

  10.1002/chem.201002553

文献信息

• Ferric Chloride Hexahydrate-Catalyzed Highly Regio- and Stereoselective Conjugate Addition Reaction of 2,3-Allenoates with Grignard Reagents: An Efficient Synthesis of β,γ-Alkenoates
  作者：Guobi Chai、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1002/adsc.200900091

  日期：2009.8

  Ferric chloride hexahydrate was shown to be an efficient catalyst for the conjugate addition of 2,3-allenoates with alkyl-, aryl-, or vinyl-Grignard reagents to synthesize polysubstituted β,γ-unsaturated alkenoates with high regio- and stereoselectivity. The in situ formed magnesium dienolate may readily react with different electrophilic reagents under different reaction conditions with or without

  六水合氯化铁被证明是2,3-烯丙基酸酯与烷基，芳基或乙烯基格氏试剂共轭加成以合成具有高区域和立体选择性的多取代的β，γ-不饱和烯酸酯的有效催化剂。在原位形成二烯醇镁可以容易地与具有或不具有催化剂不同的反应条件下不同亲电试剂反应以构建在酯基团的α位和碳-碳双键的stereocontrollable保留烯丙基季碳。
• Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor™: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates
  作者：Bo Lü、Chunling Fu、Shengming Ma

  DOI：10.1039/b917793k

  日期：——

  Different from the reaction of 2,3-allenoic acids with Selectfluor™, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor™ under different conditions in moderate yields. The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed.

  与2,3-烯酸与Selectfluor™反应不同，在不同条件下，2,4-取代的2,3-烯酸酯与Selectfluor™反应，能够高选择性地生成4-氟-2(5H)-呋喃酮和(E)-3-氟-4-氧代-2-烯酸酯，产率适中。2,4,4-三取代的2,3-烯酸酯的反应在不同条件下高选择性地生成相应的4-氟-2(5H)-呋喃酮，产率高达95%。对底物的范围进行了仔细探讨。由于与2,3-烯酸相比，2,3-烯酸酯更易获得，因此合成了新的4-氟-2(5H)-呋喃酮。基于小量氟羟基化产物E-5m的分离和表征，提出了一种机制。
• Synthesis and Biological Activity of the Structural Analogues of (—)-Cabenegrin A-I
  作者：Katalin Gulácsi、György Litkei、Sándor Antus、Csaba Szántay、László L. Darkó、Judith Szelényi、György Haskó、Szilveszter E. Vizi

  DOI：10.1002/1521-4184(200102)334:2<53::aid-ardp53>3.0.co;2-c

  日期：2001.2

  butanol derivatives (6a—j, 12, 13, 15, 17, 24b,c, 26, 27a,b) were prepared from the readily available resorcinol derivatives 2a—f and 7‐hydroxy‐chroman (18). The products were tested for inhibitory activity on the LPS‐induced TNF‐α production in the plasma in comparison with that of cabenegrin A‐I (1a).

  从容易获得的间苯二酚衍生物 2a-f 和 7-羟基色满 (18) 制备了一系列苯基丁烯和丁醇衍生物 (6a-j, 12, 13, 15, 17, 24b,c, 26, 27a,b) . 与 Cabenegrin A-I (1a) 相比，测试了这些产品对血浆中 LPS 诱导的 TNF-α 产生的抑制活性。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。
• 10.1021/acs.orglett.4c01730
  作者：Shi, Yaqi、Fu, Chunling、Zheng, Jian、Ma, Shengming

  DOI：10.1021/acs.orglett.4c01730

  日期：——

  Photoinduced cyclization of 2,3-allenoic acids with sulfonyl chloride providing an efficient synthesis of 4-sulfonylated furan-2(5H)-ones under mild reaction conditions has been achieved. The reaction enjoys a high chemoselectivity and tolerates a wide range of functional groups. The catalytic cycle has been validated through control experiments, cyclic voltammetry studies, and Stern–Volmer quenching

  已经实现了 2,3-联烯酸与磺酰氯的光诱导环化，从而在温和的反应条件下有效合成了 4-磺酰化呋喃-2(5 H )-酮。该反应具有较高的化学选择性并能耐受多种官能团。催化循环已通过对照实验、循环伏安研究和 Stern-Volmer 猝灭研究得到验证。