4-Methylpent-4-en-2-inyl-prop-2-inylether | 42502-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Methylpent-4-en-2-inyl-prop-2-inylether
• 英文别名: 2-methyl-5-prop-2-ynyloxy-pent-1-en-3-yne；4-Methyl-pent-4-en-2-yn-1-yl prop-2-yn-1-yl ether；2-methyl-5-prop-2-ynoxypent-1-en-3-yne
• CAS: 42502-51-2
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: RCHQJPCZGZKMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Methylpent-4-en-2-inyl-prop-2-inylether 、 (Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以23%的产率得到9-(4-Methyl-pent-4-en-2-ynyloxymethyl)-10-vinyl-benzo[c]chromen-6-one
  参考文献：
  名称：

  Synthesis of 6H-Dibenzo[b,d]pyran-6-ones from Aryl 3-Bromopropenoates via a Sequential One-Pot Procedure Using the Sonogashira Coupling−Benzannulation Reaction

  摘要：

  Various kinds of 6H-dibenzo [b,d] pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo [b,d] pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate le, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.

  DOI：

  10.1021/jo025659x
• 作为产物：
  描述：

  4-甲基-4-戊烯-2-炔-1-醇 、 3-溴丙炔 在 sodium hydride 作用下， 生成 4-Methylpent-4-en-2-inyl-prop-2-inylether
  参考文献：
  名称：

  Bartlett,A.J. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1315 - 1320

  摘要：

  DOI：

文献信息

• BARTLETT A. J.; LAIRD T.; OLLIS W. D., J. CHEM. SOC. PERKIN TRANS. PART I <JCPK-BH>, 1975, NO 14, 1315-1320
  作者：BARTLETT A. J.、 LAIRD T.、 OLLIS W. D.

  DOI：——

  日期：——