4-methyl-3-methylene-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide | 38066-32-9

• 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: 4-methyl-3-methylene-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide
• 英文别名: (Me)(CH2)C4H3P(S)Ph；Sulfid des Phenyl-1-methylen-3-methyl-4-phospholen-4；4-methyl-3-methylidene-1-phenyl-1-sulfanylidene-2H-1lambda5-phosphole；4-methyl-3-methylidene-1-phenyl-1-sulfanylidene-2H-1λ5-phosphole
• CAS: 38066-32-9
• 化学式: C₁₂H₁₃PS
• 分子量: 220.275
• InChiKey: LPZIZOTUBUFDDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  327.6±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-methyl-3-methylene-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide 在 nickelocene 、 碘甲烷 、 potassium cyanide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (Me)(CH2)C4H3PPh
  参考文献：
  名称：

  Boosting the Nucleophilicity of Phosphole Lone Pairs by Isomerization

  摘要：

  The phosphole isomer 4c can be obtained by nickelocene reduction complexation from the corresponding sulfide. It displays a ligating ability comparable to that of tristert-butylphosphine, and its [LPdCl2](2) complex efficiently catalyzes the deboronation homocoupling of arylboronic acids.

  DOI：

  10.1021/om100423r
• 作为产物：
  描述：

  3,4-dimethyl-1-phenylphosphole-1-sulfide 在 sodium hexamethyldisilazane 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以70%的产率得到4-methyl-3-methylene-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide
  参考文献：
  名称：

  The Chemistry of 3-Aminophospholes

  摘要：

  A 3-morpholinophosphole has been prepared from the appropriate 3-keto-4-phospholene oxide by reaction with morpholine in the presence of TiCl(4) as a catalyst, followed by reduction of the phosphoryl group by phenylsilane. Both theoretical and experimental studies show that the amino group enhances the reactivity of the diene but does not affect the lone pair at phosphorus. This observation has been used to devise a generating system for the transient phosphinidene complex [PhP-Fe(CO)(4)] that has been trapped by alkynes and ethanol.

  DOI：

  10.1021/om100085c

文献信息

• Amin, Md.; Holah, David G.; Hughes, Alan N., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 513 - 522
  作者：Amin, Md.、Holah, David G.、Hughes, Alan N.、Rukachaisirikul, Thitima

  DOI：——

  日期：——
• AMIN, MD.;HOLAH, D. G.;HUGHES, A. N.;RUKACHAISIRUKUL, THITIMA, J. HETEROCYCL. CHEM., 1985, 22, N 2, 513-522
  作者：AMIN, MD.、HOLAH, D. G.、HUGHES, A. N.、RUKACHAISIRUKUL, THITIMA

  DOI：——

  日期：——
• Boosting the Nucleophilicity of Phosphole Lone Pairs by Isomerization
  作者：Ana Ciric、François Mathey

  DOI：10.1021/om100423r

  日期：2010.11.8

  The phosphole isomer 4c can be obtained by nickelocene reduction complexation from the corresponding sulfide. It displays a ligating ability comparable to that of tristert-butylphosphine, and its [LPdCl2](2) complex efficiently catalyzes the deboronation homocoupling of arylboronic acids.
• The Chemistry of 3-Aminophospholes
  作者：Wei Luo、Ana Ciric、Rongqiang Tian、François Mathey

  DOI：10.1021/om100085c

  日期：2010.4.12

  A 3-morpholinophosphole has been prepared from the appropriate 3-keto-4-phospholene oxide by reaction with morpholine in the presence of TiCl(4) as a catalyst, followed by reduction of the phosphoryl group by phenylsilane. Both theoretical and experimental studies show that the amino group enhances the reactivity of the diene but does not affect the lone pair at phosphorus. This observation has been used to devise a generating system for the transient phosphinidene complex [PhP-Fe(CO)(4)] that has been trapped by alkynes and ethanol.