5-chloro-4-methyl-1-pentyne | 863234-24-6

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 5-chloro-4-methyl-1-pentyne
• 英文别名: 5-Chloro-4-methylpent-1-yne
• CAS: 863234-24-6
• 化学式: C₆H₉Cl
• mdl: MFCD19233155
• 分子量: 116.59
• InChiKey: MNNOLBKEVODAHX-UHFFFAOYSA-N

物化性质

• 沸点：
  130.4±23.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 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：

  5-chloro-4-methyl-1-pentyne 、 4-二氟化碘甲苯 在 氟硼酸钠 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以74%的产率得到C₁₃H₁₆ClFI⁽¹⁺⁾*BF₄^(1-)
  参考文献：
  名称：

  Internal Delivery of Soft Chlorine and Bromine Atoms:  Stereoselective Synthesis of (E)-β-Halogenovinyl(aryl)-λ³-iodanes through Domino λ³-Iodanation−1,4-Halogen Shift−Fluorination of Alkynes

  摘要：

  4-(Difluoroiodo)toluene-induced domino lambda(3)-iodanation-1,4-halogen shift-ring enlargement-fluorination reaction of 5-halopentynes with a four-, five-, or six-membered carbocycle afforded the ring-expanded (E)-delta-fluoro-beta-halovinyl-lambda(3)-iodanes stereoselectively in high yields, probably via the intermediacy of five-membered halonium ions. Use of internal alkynes makes it possible to synthesize tetrasubstituted beta-halovinyl-lambda(3)-iodanes with defined stereochemistry.

  DOI：

  10.1021/ol071345q
• 作为产物：
  描述：

  toluene-4-sulfonic acid 2-methyl-pent-4-ynyl ester 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以52%的产率得到5-chloro-4-methyl-1-pentyne
  参考文献：
  名称：

  Synthesis and Characterization of β-Haloalkenyl-λ³-bromanes:  Stereoselective Markovnikov Addition of Difluoro(aryl)-λ³-bromane to Terminal Acetylenes

  摘要：

  Reported here for the first time are the synthesis, isolation, and characterization of hypervalent beta-haloalkenyl-lambda3-bromanes. Exposure of terminal alkynes to p-trifluoromethylphenyl(difluoro)-lambda3-bromane activated by BF3-i-Pr2O resulted in fluoro-lambda3-bromanation of the triple bonds in a Markovnikov fashion, yielding (E)-beta-fluoroalkenyl-lambda3-bromanes stereoselectively in good yields. 5-Chloro-1-pentynes undergo domino lambda3-bromanation-chlorine shift-fluorination or lambda3-bromanation-chlorine shift-alkyl shift-fluorination reaction, depending on the substituents and afford (E)-beta-chloroalkenyl-lambda3-bromanes stereoselectively in high yields. The beta-chloroalkenyl-lambda3-bromanes contain three kinds of halogen atoms, F, Cl, and Br, in the molecule.

  DOI：

  10.1021/ja051690f