(Z)-8-(methoxymethoxy)-2-methyl-2-octen-4-yn-1-ol | 148457-24-3

• 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: (Z)-8-(methoxymethoxy)-2-methyl-2-octen-4-yn-1-ol
• 英文别名: (Z)-8-(methoxymethoxy)-2-methyloct-2-en-4-yn-1-ol
• CAS: 148457-24-3
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: NFESJYCZHXFZIF-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (Z)-8-(methoxymethoxy)-2-methyl-2-octen-4-yn-1-ol 在 18-冠醚-6 、 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到2-<4-(methoxymethoxy)butyl>-4-methylfuran
  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
• 作为产物：
  描述：

  (Z)-ethyl-8-(methoxxymethoxy)-2-methyl-2-octen-4-ynoate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到(Z)-8-(methoxymethoxy)-2-methyl-2-octen-4-yn-1-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：——