1,1-Diphenyl-1lambda5-phosphacyclopent-5-ene | 113705-06-9

• 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: 1,1-Diphenyl-1lambda5-phosphacyclopent-5-ene
• 英文别名: 1,1-diphenyl-1λ5-phosphacyclopent-5-ene
• CAS: 113705-06-9
• 化学式: C₁₆H₁₇P
• 分子量: 240.285
• InChiKey: JNMCREXBJCOBMC-UHFFFAOYSA-N

物化性质

• 沸点：
  390.9±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  1,1-Diphenyl-1lambda5-phosphacyclopent-5-ene 在 Raney Ni (W-2) 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 6-(diphenylphosphinoyl)bicyclo[5.3.0]decane
  参考文献：
  名称：

  Reaction of a Cyclic Phosphonium Ylide with α,β-Unsaturated Thioesters

  摘要：

  The tandem Michael-intramolecular Wittig reactions of a five-membered cyclic phosphonium ylide (2) with alpha,beta-unsaturated thioesters afforded cycloheptene derivatives 4a-g in 29-58% yield. The reaction proceeded via a rigid phosphabicyclic intermediate and supplied the cycloheptene derivatives with high stereoselectivity. On the other hand, although the reaction using S-cyclohexyl cyclopentenethioearboxylate 5a as a substrate gave a 1:1 mixture of cis and trans adducts of the corresponding hydroazulene derivatives, the reaction of S-tert-butyl cyclopentenethiocarboxylate 5b gave cis-adduct as a major product (cis:trans = 17:3).

  DOI：

  10.1021/jo990528q
• 作为产物：
  描述：

  4-diphenylphosphanyl-butan-1-ol 在 氢溴酸 、 碳酸氢钠 、 sodium carbonate 作用下， 生成 1,1-Diphenyl-1lambda5-phosphacyclopent-5-ene
  参考文献：
  名称：

  Cyclic phosphonium ylides. A short synthesis of gossyplure

  摘要：

  DOI：

  10.1021/jo00315a049

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，
• Diastereoselective Synthesis of a Hydroazulene Derivative by Tandem Michael-Wittig Reactions
  作者：Tomoko Nagao、Masayoshi Isozaki、Tetsuya Fujimoto、Iwao Yamamoto

  DOI：10.1080/10426500213400

  日期：2002.8

  The reaction of a cyclic phosphonium ylide [ 1 ] with enoate 2 gives a hydroazulene derivative with stereoselectivity.

  环状鏻叶立德 [1] 与烯酸酯 2 反应生成具有立体选择性的氢化茚衍生物。
• Mechanism of the Wittig reaction: the role of substituents at phosphorus
  作者：E. Vedejs、C. F. Marth

  DOI：10.1021/ja00220a037

  日期：1988.6
• Reaction of a Cyclic Phosphonium Ylide with α,β-Unsaturated Thioesters
  作者：Narumi Kishimoto、Tetsuya Fujimoto、Iwao Yamamoto

  DOI：10.1021/jo990528q

  日期：1999.8.1

  The tandem Michael-intramolecular Wittig reactions of a five-membered cyclic phosphonium ylide (2) with alpha,beta-unsaturated thioesters afforded cycloheptene derivatives 4a-g in 29-58% yield. The reaction proceeded via a rigid phosphabicyclic intermediate and supplied the cycloheptene derivatives with high stereoselectivity. On the other hand, although the reaction using S-cyclohexyl cyclopentenethioearboxylate 5a as a substrate gave a 1:1 mixture of cis and trans adducts of the corresponding hydroazulene derivatives, the reaction of S-tert-butyl cyclopentenethiocarboxylate 5b gave cis-adduct as a major product (cis:trans = 17:3).
• Cyclic phosphonium ylides. A short synthesis of gossyplure
  作者：Joseph M. Muchowski、Michael C. Venuti

  DOI：10.1021/jo00315a049

  日期：1981.1