(3-carboxypropyl)triphenylphosphonium iodide | 113038-84-9

• 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: (3-carboxypropyl)triphenylphosphonium iodide
• 英文别名: 2-carboxyethyl(triphenyl)phosphanium;iodide
• CAS: 113038-84-9
• 化学式: C₂₁H₂₀O₂P*I
• 分子量: 462.267
• InChiKey: KLOZOIVMBFPGHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-propionaldehyde 、 (3-carboxypropyl)triphenylphosphonium iodide 在 potassium 2-methylbutan-2-olate 作用下， 生成 (Z)-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hept-4-enoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homoprosta-5-enoic acid analogs as thromboxane A2 receptor antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha, 2 alpha(Z),3 alpha(1E,3S*,4R*),4 alpha]-7-[3-(3-hydroxy-4-phenyl-1-pentenyl)-7- oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (4), was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Alcohol 4 was the only member in a series of allylic alcohols which did not display direct contractile activity in the rat stomach strip model. Alcohol 4 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-rich plasma (I50 = 0.65 +/- 0.1 microM); (b) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (pA2 = 8.0 +/- 0.2) or rat aorta (pA2 = 8.1 +/- 0.2); and (c) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (1 mg/kg iv). A radioiodinated analogue of 4 bound in a specific and saturable manner to human platelet membranes with a Kd = 2.3 +/- 0.9 nM. Modification of the alpha-chain, in an attempt to minimize in vivo metabolism, resulted in TxA2 receptor antagonists of reduced in vitro potency.

  DOI：

  10.1021/jm00168a032
• 作为产物：
  描述：

  3-碘丙酸 、 三苯基膦 以 甲苯 为溶剂， 反应 24.0h， 生成 (3-carboxypropyl)triphenylphosphonium iodide
  参考文献：
  名称：

  官能化phospho基离子液体可作为由过氧化物和二氧化碳合成环状碳酸酯的有效催化剂

  摘要：

  通过一种简单的方法合成了一系列新颖的功能化phospho基离子液体（FPBIL），并首先评估了在不存在助催化剂和溶剂的情况下，通过将CO 2环化成环氧化物来合成环状碳酸酯的催化剂。FPBIL在环加成反应中表现良好，尤其是羧基官能化反应。在[Ph 3 PC 2 H 4 COOH] Br上，碳酸亚丙酯在130°C和3小时内在2.5 MPa下的产率为97.3％（TOF = 64.9 h -1）。偏振的协同作用通过氢键和Br的亲核攻击诱导的-负离子具有出色的性能。此外，具有中等亚甲基链长的FPBIL显示出优异的催化活性。这是因为它们在strong阳离子和卤化物阴离子之间具有强酸性和弱的静电相互作用。强酸性有利于化环氧的开环和弱静电相互作用增强BR的亲核攻击能力- 。可以设想，无金属和无溶剂工艺具有将CO 2催化转化为增值化学品的高潜力。

  DOI：

  10.1016/j.apcata.2013.10.060

文献信息

• Concise Synthesis of (3<i>Z</i>)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer
  作者：P. D. Mayo、P. J. Silk、D. I. MaGee、J. McConaghy

  DOI：10.1080/00397911.2014.881497

  日期：2014.7.3

  Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a 2:1 blend of (3Z)-dodecen-12-olide and (3E)-dodecen-12-olide starting from commercially available (2-carboxyethyl)triphenylphosphonium bromide and 10-bromo-1-decene is described. The key steps in this synthesis are a lithium-salt-free Wittig reaction and an intramolecular S(N)2 esterification. Both of these macrocyclic lactones are behaviorally active toward EAB, and the 2:1 blend whose synthesis is described here has the potential to be a detection agent, mating disruptor, or mass trapping agent, which could be used in the control of EAB.