1-phenyl-2-phospholene-1-sulfide | 52988-62-2

• 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-phenyl-2-phospholene-1-sulfide
• 英文别名: 1-phenyl-2-phospholen-1-sulfide；1-Phenyl-2-phospholen-1-sulfid；1-Phenyl-1-sulfanylidene-2,3-dihydro-1lambda5-phosphole；1-phenyl-1-sulfanylidene-2,3-dihydro-1λ5-phosphole
• CAS: 52988-62-2
• 化学式: C₁₀H₁₁PS
• 分子量: 194.237
• InChiKey: JQSYESKKWJGZQV-UHFFFAOYSA-N

物化性质

• 沸点：
  299.4±33.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-phospholene-1-sulfide 在 n 作用下， 以 四氢呋喃 为溶剂， 生成 1-phenyl-2,3-dihydro-1H-phosphole
  参考文献：
  名称：

  [Cp 2 ZrHCl] n在磷化学中有用的还原剂

  摘要：

  描述了用[Cp 2 ZrHCl] n选择性还原PO，PS，>CC<，CO键，以及卤化物交换的方法。

  DOI：

  10.1016/s0040-4039(97)01365-8
• 作为产物：
  描述：

  1-phenyl-2-phospholene-1-oxide 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 生成 1-phenyl-2-phospholene-1-sulfide
  参考文献：
  名称：

  Kinetic Resolution in 1,3-Dipolar Cycloaddition of Tartaric Acid-Derived Nitrones to 2,3-Dihydro-1-phenyl-1H-phospholes. An Enantioselective Approach to the 2,2'-Coupled Pyrrolidine-Phospholane Ring System

  摘要：

  Enantiomerically pure five-membered ring nitrones derived from L-tartaric acid via C2-symmetric O,O'-protected 3,4-dihydroxy pyrrolidines undergo highly regio- and stereoselective cycloaddition reactions with racemic 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide and 1-sulfide. In all cases formation of only two diastereomeric cycloadducts is observed and their ratio (up to 10:1) is dependent on the size of the protecting groups in the nitrone and on the extent of conversion. The tricyclic cycloadducts feature 2,2'-connection of pyrrolidine and phospholane rings and six contiguous stereogenic centers of which three are created and the one at phosphorus is kinetically resolved during the cycloaddition process. It is established that in the studied kinetic resolutions the stereoselectivity factor 8 = k(S)/k(R) exceeds the value of 10 (up to 14) in the most favorable cases. In a properly tuned reaction both the diastereomeric cycloadducts and the enantiomerically enriched dihydrophosphole derivative can be simultaneously obtained in satisfactory chemical and optical yields.

  DOI：

  10.1021/jo00085a019

文献信息

• Raney-Ni reduction of phosphine sulfides
  作者：Oleg M. Demchuk、Wioletta Świerczyńska、Kamil Dziuba、Sławomir Frynas、Anna Flis、K. Michał Pietrusiewicz

  DOI：10.1080/10426507.2016.1225052

  日期：2017.1.2

  GRAPHICAL ABSTRACT ABSTRACT A variety of tertiary phosphine sulfides have been reduced by Raney-Ni to give the corresponding phosphines with high efficiency and under mild conditions. Alkyl, aryl, acyclic, cyclic, as well as sterically crowded phosphine sulfides are reduced with equal facility. Optically active P-stereogenic phosphine sulfides are reduced stereospecifically with clean retention of

  图形摘要 摘要 多种叔膦硫化物已被 Raney-Ni 还原，在温和的条件下高效地生成相应的膦。烷基、芳基、无环、环状以及空间拥挤的硫化膦用相同的设备还原。光学活性的 P-立体异构膦硫化物被立体定向​​地还原，并在 P 处保持构型的清洁。不饱和硫化膦的还原不是完全化学选择性的，并且伴随着双键的部分还原而发生。通过在 H2 气氛（气球）下进行还原，可以一步实现将不饱和膦硫化物完全还原为相应的完全饱和膦。
• Low temperature stable polymethylene polyphenylene polyisocyanates
  申请人：BASF Corporation

  公开号：EP0189156A2

  公开（公告）日：1986-07-30

  Low temperature stable polymethylene polyphenylene polyisocyanates are composed of crude polymethylene polyphenylene polyisocyanate containing from about 50 to about 80 percent by weight 2-ring diphenylmethane diisocyanate wherein from about 65 to about 93 weight percent of the 2-ring diisocyanate is 4,4'- and from about 7 to about 35 weight percent is 2,4'- and furthermore the composition contains from about 1 to about 5 weight percent carbodiimide- uretonimine structure. The polyisocyanates are useful in preparing polyurethane foams.

  低温稳定聚亚甲基多苯基多异氰酸酯由粗聚亚甲基多苯基多异氰酸酯组成，其中含有约 50%至约 80%（重量百分比）的 2-环二苯基甲烷二异氰酸酯，其中约 65%至约 93%（重量百分比）的 2-环二异氰酸酯为 4,4'-，约 7%至约 35%（重量百分比）的 2,4'-，此外，该组合物还含有约 1%至约 5%（重量百分比）的碳二亚胺-脲基亚胺结构。多异氰酸酯可用于制备聚氨酯泡沫。
• Stable 4,4'-diphenylmethane diisocyanates
  申请人：BASF Corporation

  公开号：EP0193787A2

  公开（公告）日：1986-09-10

  Stable 4,4'-diphenylmethane diisocyanates are composed of 4,4'-diphenylmethane diisocyanates containing from about 2 to about 10 weight percent carbodiimide-uretonimine structure. The diisocyanates are useful in preparing polyurethane foams.

  稳定的 4,4'-二苯基甲烷二异氰酸酯由 4,4'-二苯基甲烷二异氰酸酯组成，含有约 2 至约 10 重量百分比的碳二亚胺-脲基亚胺结构。这种二异氰酸酯可用于制备聚氨酯泡沫。
• Liquid carbodiimide-uretonimine-modified polyphenylene polyisocyanates and polyurethane foams made therefrom
  申请人：BASF Corporation

  公开号：EP0308710A1

  公开（公告）日：1989-03-29

  A process for the preparation of liquid poly­methylene polyphenylene polyisocyanate blends containing carbodiimide-uretonimine isocyanate linkages, containing a high two-ring methylene bis(phenylisocyanate) content, and light colored polyurethane foams made therefrom. The process is comprised of reacting polymethylene polyphenylene polyisocyanate with a catalytically effective amount of a carbodiimide-uretonimine promoting compound at a temperature sufficient to promote the formation of carbodiimide-­uretonimine linkages and an isocyanate content of about 25 percent and the desired viscosity is reached, and then reacting that product to deactivate the carbodiimide-­uretonimine catalyst, and finally blending two ring methylene bis(phenylisocyanate) with the product to produce a mixture having a two ring isocyanate content of about 60 percent of the total ring content and a viscosity comparable to standard polymeric MDI. Urethane foams made from this material are lighter in color than those formed from standard polymeric MDI.

  一种用于制备含有碳二亚胺-脲基亚胺异氰酸酯链节的液态聚亚甲基多苯基多异氰酸酯混合物的工艺，该混合物含有较高的二环亚甲基双(苯基异氰酸酯)含量，以及由其制成的浅色聚氨酯泡沫。该工艺包括：在足以促进形成碳二亚胺-质子酰亚胺链节的温度下，将聚亚甲基多苯基多异氰酸酯与催化有效量的碳二亚胺-质子酰亚胺促进化合物反应，异氰酸酯含量约为 25%，并达到所需的粘度、然后对该产品进行反应，使碳二亚胺-脲基亚胺催化剂失活，最后将二环亚甲基双（苯基异氰酸酯）与该产品混合，生成一种混合物，其二环异氰酸酯含量约占总环含量的 60%，粘度与标准聚合 MDI 相当。用这种材料制成的聚氨酯泡沫的颜色比用标准聚合 MDI 形成的泡沫浅。
• Low temperature active aliphatic/aromatic polycarbodiimides
  申请人：UNION CARBIDE CHEMICALS AND PLASTICS COMPANY INC. (a New York corporation)

  公开号：EP0449143A2

  公开（公告）日：1991-10-02

  A mixed aliphatic/aromatic polycarbodiimide prepared by first polymerizing an aliphatic isocyanate or mixture thereof, optionally in the presence of a polyfunctional isocyanate; arresting polymer chain growth by reaction with a stoichiometrically deficient amount of a monofunctional isocyanate-reactive compound, followed by further polymerization with an aromatic diisocyanate.

  一种脂肪族/芳香族混合聚碳二亚胺，其制备方法是：首先聚合脂肪族异氰酸酯或其混合物，可选择在有多官能团异氰酸酯存在的情况下进行；通过与按化学计量不足量的单官能团异氰酸酯反应化合物反应，阻止聚合物链增长，然后与芳香族二异氰酸酯进一步聚合。