10-(Methoxymethoxy)-4-methylidenedec-5-yn-3-ol | 148457-03-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10-(Methoxymethoxy)-4-methylidenedec-5-yn-3-ol
• CAS: 148457-03-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: VZRMTVXTIPTVJY-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±37.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(Methoxymethoxy)-4-methylidenedec-5-yn-3-ol 在 silica gel 、 silver nitrate 作用下， 以 正己烷 为溶剂， 反应 0.25h， 以99%的产率得到2-Ethyl-5-[4-(methoxymethoxy)butyl]-3-methylfuran
  参考文献：
  名称：

  Synthesis of Furans and 2,5-Dihydrofurans by Ag(I)-Catalyzed Isomerization of Allenones, Alkynyl Allylic Alcohols, and Allenylcarbinols

  摘要：

  DOI：

  10.1021/jo00123a040
• 作为产物：
  描述：

  乙基乙炔基甲醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四乙基溴化铵 、 氢溴酸 作用下， 以 二氯甲烷 、 二乙胺 为溶剂， 反应 3.0h， 生成 10-(Methoxymethoxy)-4-methylidenedec-5-yn-3-ol
  参考文献：
  名称：

  Synthesis of furans by base-catalyzed cyclization-isomerization of .beta.- and .gamma.-alkynyl allylic alcohols

  摘要：

  Beta- and gamma-alkylyl allylic alcohols 3, 13, 26, available through Pd-mediated coupling of appropriate vinylic halides and terminal alkynes, cyclize and subsequently isomerize to furans 4, 17, and 32 upon treatment with KO-t-Bu in t-BuOH-THF at 25-60-degrees-C. The methodology has been used to prepare 2,3-, 2,4-, and 2,3,5-substituted furans. Reactions in t-BuOD as cosolvent lead to deuterium incorporation consistent with concurrent pathways in which direct 5-exo-dig or 5-endo-dig cyclization of the alkynyl allylic alcohol competes with prior isomerization to an allene intermediate which subsequently cyclizes by 5-exo- or 5-endo-dig pathways.

  DOI：

  10.1021/jo00064a038

文献信息

• Marshall James A., DuBay William J., J. Org. Chem., 58 (1993) N 12, S 3435-3443
  作者：Marshall James A., DuBay William J.

  DOI：——

  日期：——
• Synthesis of furans by base-catalyzed cyclization-isomerization of .beta.- and .gamma.-alkynyl allylic alcohols
  作者：James A. Marshall、William J. DuBay

  DOI：10.1021/jo00064a038

  日期：1993.6

  Beta- and gamma-alkylyl allylic alcohols 3, 13, 26, available through Pd-mediated coupling of appropriate vinylic halides and terminal alkynes, cyclize and subsequently isomerize to furans 4, 17, and 32 upon treatment with KO-t-Bu in t-BuOH-THF at 25-60-degrees-C. The methodology has been used to prepare 2,3-, 2,4-, and 2,3,5-substituted furans. Reactions in t-BuOD as cosolvent lead to deuterium incorporation consistent with concurrent pathways in which direct 5-exo-dig or 5-endo-dig cyclization of the alkynyl allylic alcohol competes with prior isomerization to an allene intermediate which subsequently cyclizes by 5-exo- or 5-endo-dig pathways.
• Synthesis of Furans and 2,5-Dihydrofurans by Ag(I)-Catalyzed Isomerization of Allenones, Alkynyl Allylic Alcohols, and Allenylcarbinols
  作者：James A. Marshall、Clark A. Sehon

  DOI：10.1021/jo00123a040

  日期：1995.9