1,1-diphenylphospholanium perchlorate | 55759-75-6

• 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: 1,1-diphenylphospholanium perchlorate
• 英文别名: 1,1-Diphenylphospholan-1-ium;perchlorate
• CAS: 55759-75-6
• 化学式: C₁₆H₁₈P*ClO₄
• 分子量: 340.743
• InChiKey: XHFRNEJFZWDCJQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-diphenylphospholanium perchlorate 在 正丁基锂 作用下， 反应 3.0h， 生成 (E)-12-(diphenylphosphinyl)-9-(methylthio)-8-dodecene
  参考文献：
  名称：

  Chemistry of cyclic phosphorus compounds. 3. Synthesis of pheromones having an .gamma.,.delta.-unsaturated ketone system from 1,1-diphenylphospholanium perchlorate

  摘要：

  DOI：

  10.1021/jo00265a006
• 作为产物：
  描述：

  4-diphenylphosphanyl-butan-1-ol 生成 1,1-diphenylphospholanium perchlorate
  参考文献：
  名称：

  Rapid method of preparation of phospholanium perchlorates via intramolecular cyclizations of 4-hydroxybutylorganophosphines

  摘要：

  DOI：

  10.1021/jo00907a021

文献信息

• Diastereoselective Tandem Michael−Intramolecular Wittig Reactions of a Cyclic Phosphonium Ylide with 8-Phenylmenthyl Enoates
  作者：Tomoko Nagao、Takanori Suenaga、Takao Ichihashi、Tetsuya Fujimoto、Iwao Yamamoto、Akikazu Kakehi、Ryozo Iriye

  DOI：10.1021/jo001379a

  日期：2001.2.1

  diastereoselectivity of the initial tandem reactions was estimated to be 94:6 from the 31P NMR of a mixture of the diastereomeric ketal derivatives 6a and 6'a which were obtained by the reaction of 5a with (2R,3R)-2,3-butanediol, and the absolute configuration of the major isomer was determined by the single-crystal X-ray analysis. Similar reactions using some 8-phenylmenthyl alkenoates were attempted. As a result

  研究了使用8-苯基薄荷基烯酸酯的五元环状phospho叶立德2的非对映选择性串联Michael-分子内Wittig反应。磷鎓叶立德与肉桂酸8-苯基薄荷基酯反应，然后水解得到的烯醇醚4a，得到（3R，4S）-4-（二苯基膦基）-3-苯基环庚酮（3R，4S）-5a作为主要异构体。从通过5a与（2R，3R）-2,3-反应获得的非对映体缩酮衍生物6a和6'a的混合物的31P NMR估算，初始串联反应的非对映选择性为94：6。丁二醇和主要异构体的绝对构型由单晶X射线分析确定。尝试使用一些8-苯基薄荷基链烯酸酯进行类似的反应。结果是，
• Synthesis of cycloheptenyldiphenylphosphine oxides from the reactions of a cyclic phosphonium salt with α,β-unsaturated carbonyl compounds
  作者：Tetsuya Fujimoto、Yukiharu Takeuchi、Koh-Ichi Kai、Yukihiko Hotei、Kazuchika Ohta、Iwao Yamamoto

  DOI：10.1039/c39920001263

  日期：——

  The reactions of the ylide from the five-membered cyclic phosphonium salt 1 with methyl vinyl ketone, chalcone, and benzylidene acetone afforded cycloheptenyldiphenylphosphine oxides via a Michael-type reaction followed by an intramolecular Wittig reaction.

  五元环状膦盐 1 的桎梏与甲基乙烯酮、查尔酮和亚苄基丙酮反应，通过迈克尔式反应和分子内维蒂希反应生成环庚烯二苯基膦氧化物。
• [2+2] Cycloaddition and ring expansion reactions of cyclic phosphonium and aminophosphonium salts: synthesis and structure of the first eight-membered ylide-type heterocycles
  作者：Tetsuya Uchiyama、Tetsuya Fujimoto、Akikazu Kakehi、Iwao Yamamoto

  DOI：10.1039/a807891b

  日期：——

  A series of new eight-membered heterocycles, 4 and 6, was isolated from the reactions of simple six-membered aza-ylides with acetylene and nitrile derivatives. These structures were elucidated by X-ray crystal analysis. On the other hand, the reactions of five-membered ylides and aza-ylides with nitrile derivatives formed seven-membered ylides, which were hydrolyzed immediately during aqueous work-up to give phosphine oxide derivatives.

  从简单的六元氮杂环与乙炔和腈衍生物的反应中分离出一系列新的八元杂环，即 4 和 6。这些结构通过 X 射线晶体分析得以阐明。另一方面，五元醯化物和氮杂环醯化物与腈衍生物反应生成七元醯化物，这些醯化物在水处理过程中立即水解，生成氧化膦衍生物。
• Maerkl,G., Angewandte Chemie, 1963, vol. 75, # 18, p. 859 - 860
  作者：Maerkl,G.

  DOI：——

  日期：——
• Synthesis of Seven-Membered Cyclic Enol Ether Derivatives from the Reaction of a Cyclic Phosphonium Ylide with α,β-Unsaturated Esters
  作者：Tetsuya Fujimoto、Yoh-ichi Kodama、Iwao Yamamoto、Akikazu Kakehi

  DOI：10.1021/jo970751s

  日期：1997.9.1

  The tandem Michael-intramolecular Wittig reactions of a five-membered cyclic phosphonium ylide (2) with alpha,beta-unsaturated esters afforded seven-membered cyclic enol ether derivatives 4a-e in 37-73% yield. The reaction proceeded via a rigid phosphabicyclic intermediate and supplied the enol ether derivatives with high stereoselectivity. On the other hand, the reaction using ethyl acrylate as a substrate gave the 1:3 adduct 15 of the ylide and the enoate via the repetition of the Michael-type addition and regeneration of the ylide followed by the intramolecular Wittig reaction.