(Z)-8-Methoxymethoxy-2-methyl-oct-2-en-4-ynal | 148457-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-8-Methoxymethoxy-2-methyl-oct-2-en-4-ynal
• CAS: 148457-31-2
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: MUAWMROAKNVMBO-XFFZJAGNSA-N

物化性质

• 沸点：
  284.9±30.0 °C(predicted)
• 密度：
  0.996±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-8-Methoxymethoxy-2-methyl-oct-2-en-4-ynal 在 18-冠醚-6 、 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 2-Ethyl-5-[4-(methoxymethoxy)butyl]-3-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 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.25h， 生成 (Z)-8-Methoxymethoxy-2-methyl-oct-2-en-4-ynal
  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