P-isopropyltriphenylphosphonium cation | 47180-35-8

• 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: P-isopropyltriphenylphosphonium cation
• 英文别名: triphenyl-isopropyl-phosphonium cation；i-Propyltriphenylphosphonium-Ion；Triphenyl-isopropyl-phosphonium；Isopropyltriphenylphosphonium；Triphenylisopropylphosphonium；triphenyl(propan-2-yl)phosphanium
• CAS: 47180-35-8
• 化学式: C₂₁H₂₂P
• 分子量: 305.379
• InChiKey: PXIMQGSMXJFQOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-氧代己酸甲酯 、 P-isopropyltriphenylphosphonium cation 在 正丁基锂 作用下， 生成 methyl 7-methyl-6-octenoate
  参考文献：
  名称：

  Tietze, Lutz F.; Brumby, Thomas; Brand, Siegbert, Chemische Berichte, 1988, vol. 121, p. 499 - 506

  摘要：

  DOI：

文献信息

• Intramolecular Simmons−Smith Cyclopropanation. Studies into the Reactivity of Alkyl-Substituted Zinc Carbenoids, Effect of Directing Groups and Synthesis of Bicyclo[<i>n</i>.1.0]alkanes
  作者：James A. Bull、André B. Charette

  DOI：10.1021/ja907504w

  日期：2010.2.17

  explored. Substitution on the alkene and at the allylic position was well tolerated, providing the bicyclic products in high yields. Additionally, the IMSS reaction allowed a highly diastereoselective synthesis of a 5-3-5 fused tricycloalkane. These studies will have implications for the use of substituted carbenoids in cyclopropanation reactions and for directed cyclopropanation reactions as well as in

  已经开发了分子内 Simmons-Smith (IMSS) 环丙烷化，为构建取代的双环烷烃提供了一种新方法。首先，以高收率制备了含有烯丙醇的功能化的偕二碘烷烃。然后研究了分子内环化形成不同环大小的过程，并证明可以成功合成双环[3.1.0]己烷和双环[4.1.0]庚烷。更大的链长导致含末端烯烃的产物。Analysis of the product distribution for the different ring sizes and under various reaction conditions provided insight into the reactivity of substituted zinc carbenoids, and by the appropriate choice of conditions cyclopropanation could be promoted
• The rational design of modified Cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes
  作者：Alain Merschaert、Pieter Delbeke、Désiré Daloze、Georges Dive

  DOI：10.1016/j.tetlet.2004.04.090

  日期：2004.6

  step is the intramolecular conjugate addition of a phenolic nucleophile on a α,β-unsaturated ester catalyzed by Cinchona alkaloids. The high ee’s obtained with cinchonine and its derivatives have been rationalized by ab initio quantum chemistry calculations of transition state structures.

  已经实现了2-取代的手性苯并二氢吡喃的新的不对称合成。关键步骤是在金鸡纳生物碱催化的α，β-不饱和酯上分子内共轭酚类亲核试剂。用金鸡宁及其衍生物获得的高ee已通过对过渡态结构进行从头算量子化学计算得到合理化。
• A Stereoselective Intramolecular Retro-Ene Reaction Catalysed by Aluminium Chloride
  作者：Michal Bodajla、Graeme R Jones、Christopher A Ramsden*

  DOI：10.1016/s0040-4039(97)00404-8

  日期：1997.4

  intramolecular ionic cycloaddition of the proposed intermediate arenoxenium cations. Treatment of the same precursors with aluminium chloride results in a stereoselective intramolecular cyclisation to spiroketones. Evidence that the mechanism of formation involves a cyclic aluminium intermediate is presented. © 1997 Elsevier Science Ltd.

  5-（2-萘酚）-1-戊烯与I（III）试剂的反应导致在C-1处发生亲核取代，而不是所提议的中间体槟榔烯阳离子的[4 + 2]分子内离子环加成。用氯化铝处理相同的前体会导致立体选择性分子内环化为螺酮。提供了形成机理涉及环状铝中间体的证据。©1997爱思唯尔科学有限公司。
• THE YLID ROUTE TO FLUORODIENES
  作者：Kazumi Kondo、Sylvain Cottens、Manfred Schlosser

  DOI：10.1246/cl.1984.2149

  日期：1984.12.5

  The readily accessible 2-fluoro-2-alkenals react with phosphorus ylids at approximately the same rate and leading to nearly the same (Z/E)-mixtures of products as the corresponding halogen-free aldehydes do. Thus, the Wittig reaction allows to prepare a great variety of 2-fluorodienes with high yields.

  易于获得的 2-氟-2-烯醛与磷叶立德以大致相同的速率反应，并产生与相应的无卤醛几乎相同的 (Z/E)-产物混合物。因此，Wittig 反应允许以高产率制备多种 2-氟二烯。
• Synthesis and antifungal activity of 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide
  作者：Jin Zhao、Hong-Bo Dong、Ming-Yan Yang、Juan Du、Jia-Zheng Jiang、Ming-An Wang

  DOI：10.1080/10286020.2013.879121

  日期：2014.3.4

  The racemic 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide, the analog of natural product (6R)-3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, was totally synthesized using easily available (E)-2-(2-carboxyvinyl)benzoic acid as a raw material in nine-step reactions including three key steps of Wittig reaction, epoxidation, and cyclization, with an overall yield of 10.3%. The bioassay results showed that (+/-)-2 exhibited stronger antifungal activity than the natural product (+/-)-1 and (R)-1 against Alternaria solani with an EC50 value of 27.36g/ml.

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