(1R,2R,6S,7S)-8,9-dimethyl-4,10-diphenyl-10-sulfanylidene-4-aza-10lambda5-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione | 78177-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,2R,6S,7S)-8,9-dimethyl-4,10-diphenyl-10-sulfanylidene-4-aza-10lambda5-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• 英文别名: (1R,2R,6S,7S)-8,9-dimethyl-4,10-diphenyl-10-sulfanylidene-4-aza-10λ5-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 78177-28-3；78961-93-0
• 化学式: C₂₂H₂₀NO₂PS
• 分子量: 393.446
• InChiKey: LSCQILYKLOOKBN-YWRPIJFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1R,2R,6S,7S)-8,9-dimethyl-4,10-diphenyl-10-sulfanylidene-4-aza-10lambda5-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione 反应 1.0h， 生成 O-methyl phenylphosphinothioate
  参考文献：
  名称：

  Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives

  摘要：

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.

  DOI：

  10.1021/jo00075a014
• 作为产物：
  描述：

  (1S,2S,6R,7R)-8,9-dimethyl-4,10-diphenyl-4-aza-10-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (1R,2R,6S,7S)-8,9-dimethyl-4,10-diphenyl-10-sulfanylidene-4-aza-10lambda5-phosphatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
  参考文献：
  名称：

  Nouvelles voies d'acces aux phospha-7-norbornenes trivalents

  摘要：

  新λ 3 -7- phosphanorbornenes通过相应P-硫化物（顺式结构）的二茂镍还原络合或通过与N-苯基马来酰亚胺（抗结构）三价phospholes的直接[14 + 2]环加成制备任一。

  DOI：

  10.1016/0040-4039(81)80086-x

文献信息

• Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives
  作者：Louis D. Quin、Stefan Jankowski、Juliusz Rudzinski、Anthony G. Sommese、Xiao Ping Wu

  DOI：10.1021/jo00075a014

  日期：1993.11

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.
• Nouvelles voies d'acces aux phospha-7-norbornenes trivalents
  作者：François Mathey、François Mercier

  DOI：10.1016/0040-4039(81)80086-x

  日期：1981.1

  New λ3-7-phosphanorbornenes are prepared either through the nickelocene reduction-complexation of the corresponding P-sulfides (syn structure) or through the direct [14 + 2] cycloaddition of tervalent phospholes with N-phenylmaleimide (anti structure).

  新λ 3 -7- phosphanorbornenes通过相应P-硫化物（顺式结构）的二茂镍还原络合或通过与N-苯基马来酰亚胺（抗结构）三价phospholes的直接[14 + 2]环加成制备任一。