1-<(tert-butyldimethylsilyl)oxy>-3-methyl-3,4-undecadien-2-one | 148457-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<(tert-butyldimethylsilyl)oxy>-3-methyl-3,4-undecadien-2-one
• CAS: 148457-17-4
• 化学式: C₁₈H₃₄O₂Si
• 分子量: 310.552
• InChiKey: YEWUKXPJXPWRFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(tert-butyldimethylsilyl)oxy>-3-methyl-3,4-undecadien-2-one 在 水 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 3.58h， 生成 3-methyl-2-methylene-3,4-undecadien-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
• 作为产物：
  描述：

  (Z)-3-甲基戊-2-烯-4-炔-1-醇 在 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 草酰氯 、 copper(I) bromide dimethylsulfide complex 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.67h， 生成 1-<(tert-butyldimethylsilyl)oxy>-3-methyl-3,4-undecadien-2-one
  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：——