<(2-nitrophenyl)sulfinyl>-1,2-propadiene | 83074-75-3

• 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: <(2-nitrophenyl)sulfinyl>-1,2-propadiene
• 英文别名: (o-Nitrophenyl)(1,2-propadienyl)sulfoxid
• CAS: 83074-75-3
• 化学式: C₉H₇NO₃S
• 分子量: 209.225
• InChiKey: XLQYFDBZGHIHIX-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  448.3±15.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <(2-nitrophenyl)sulfinyl>-1,2-propadiene 在 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 10.0h， 生成 1-(o-Nitrophenylsulfinyl)-2-propanon
  参考文献：
  名称：

  Altenbach, Hans-Josef; Soicke, Hartwig, Liebigs Annalen der Chemie, 1982, # 6, p. 1096 - 1104

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硝基苯硫氯 、 2-丙炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以80%的产率得到<(2-nitrophenyl)sulfinyl>-1,2-propadiene
  参考文献：
  名称：

  (Nitroaryl)sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4 + 2 cycloaddition chemistry

  摘要：

  (Nitroaryl)sulfinyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroaryl)sulfenyl chloride and triethylamine. These activated allenes undergo 4 + 2 cycloaddition across the C1C2-pi-bond. The initially formed allylic sulfoxide readily undergoes a 2,3-sigmatropic rearrangement to produce a stable sulfenate ester that is easily cleaved with thiophilic reagents. The dienophilic reactivity of the (nitroary)sulfinyl-substituted allene is much greater than the corresponding propargyl alcohol, and the cycloaddition also proceeds with high regioselectivity. The Diels-Alder reaction of [(2-nitrophenyl)-sulfinyl]propadiene with Danishefsky's diene affords meta-substituted benzyl alcohols in high yield. Reaction of the more highly activated methyl 2-[(2-nitrophenyl)sulfinyl]-2,3-butadienoate with Danishefsky's diene followed by treatment of the resulting sulfenate ester with triethyl phosphite produces substituted phthalides in excellent yield. The (2,4-dinitrophenyl)sulfinyl-substituted allene was found to react smoothly with a variety of nitrones to give sulfenate esters of isoxazolidines. These allenyl sulfoxides correspond to formal equivalents of propargyl alcohol, which itself is too unreactive to undergo Diels-Alder chemistry or 1,3-dipolar cycloaddition with nitrones or nitrile oxides.

  DOI：

  10.1021/jo00013a033

文献信息

• PADWA, ALBERT;BULLOCK, WILLIAM H.;NORMAN, BRYAN H.;PERUMATTAM, JOHN, J. ORG. CHEM., 56,(1991) N3, C. 4252-4259
  作者：PADWA, ALBERT、BULLOCK, WILLIAM H.、NORMAN, BRYAN H.、PERUMATTAM, JOHN

  DOI：——

  日期：——
• ALTENBACH, H. -J.;SOICKE, H., LIEBIGS ANN. CHEM., 1982, N 6, 1096-1104
  作者：ALTENBACH, H. -J.、SOICKE, H.

  DOI：——

  日期：——
• (Nitroaryl)sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4 + 2 cycloaddition chemistry
  作者：Albert Padwa、William H. Bullock、Bryan H. Norman、John Perumattam

  DOI：10.1021/jo00013a033

  日期：1991.6

  (Nitroaryl)sulfinyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroaryl)sulfenyl chloride and triethylamine. These activated allenes undergo 4 + 2 cycloaddition across the C1C2-pi-bond. The initially formed allylic sulfoxide readily undergoes a 2,3-sigmatropic rearrangement to produce a stable sulfenate ester that is easily cleaved with thiophilic reagents. The dienophilic reactivity of the (nitroary)sulfinyl-substituted allene is much greater than the corresponding propargyl alcohol, and the cycloaddition also proceeds with high regioselectivity. The Diels-Alder reaction of [(2-nitrophenyl)-sulfinyl]propadiene with Danishefsky's diene affords meta-substituted benzyl alcohols in high yield. Reaction of the more highly activated methyl 2-[(2-nitrophenyl)sulfinyl]-2,3-butadienoate with Danishefsky's diene followed by treatment of the resulting sulfenate ester with triethyl phosphite produces substituted phthalides in excellent yield. The (2,4-dinitrophenyl)sulfinyl-substituted allene was found to react smoothly with a variety of nitrones to give sulfenate esters of isoxazolidines. These allenyl sulfoxides correspond to formal equivalents of propargyl alcohol, which itself is too unreactive to undergo Diels-Alder chemistry or 1,3-dipolar cycloaddition with nitrones or nitrile oxides.
• Altenbach, Hans-Josef; Soicke, Hartwig, Liebigs Annalen der Chemie, 1982, # 6, p. 1096 - 1104
  作者：Altenbach, Hans-Josef、Soicke, Hartwig

  DOI：——

  日期：——