(Z)-1-(t-butyldimethylsilyloxy)-1-methoxy-4-methylpenta-1,3-diene | 287193-91-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-1-(t-butyldimethylsilyloxy)-1-methoxy-4-methylpenta-1,3-diene
• 英文别名: tert-butyl-[(1Z)-1-methoxy-4-methylpenta-1,3-dienoxy]-dimethylsilane
• CAS: 287193-91-3
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: VVLGPNKMNGXSME-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-(t-butyldimethylsilyloxy)-1-methoxy-4-methylpenta-1,3-diene 在 正丁基锂 、 trityl tetrafluoroborate 、 四氯苯醌 、 二异丙胺 作用下， 以 四氢呋喃 、 氘代氯仿 、 正己烷 为溶剂， 反应 1.17h， 生成 methyl (E)-4-methylpenta-2,4-dienoate
  参考文献：
  名称：

  摘要：

  Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.

  DOI：

  10.1071/ch00027
• 作为产物：
  描述：

  4-甲基戊-2-烯酸(E)-乙酯 、 叔丁基二甲基氯硅烷 在 六甲基磷酰三胺 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以59%的产率得到(Z)-1-(t-butyldimethylsilyloxy)-1-methoxy-4-methylpenta-1,3-diene
  参考文献：
  名称：

  摘要：

  Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.

  DOI：

  10.1071/ch00027
• 作为试剂：
  描述：

  四氯苯醌 在 (Z)-1-(t-butyldimethylsilyloxy)-1-methoxy-4-methylpenta-1,3-diene 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以56%的产率得到四氯氰醌
  参考文献：
  名称：

  摘要：

  Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.

  DOI：

  10.1071/ch00027

文献信息

• ——
  作者：Donald W. Cameron、Ross M. Heisey

  DOI：10.1071/ch00027

  日期：——

  Reaction of certain geometrically defined 1,1-dioxy-4-alkyl- and -4,4-dialkyl-substituted buta-1,3-dienes with halogenated quinones does not involve Diels-Alder or Michael addition chemistry. Instead, rapid competitive oxidation of the dienes to give 2,4-dienoate esters was observed. This new reaction involves strong spatial association between diene and quinone, hydrogen being transferred specifically from the (4E)-alkyl group. Its scope is compared with addition of the same terminally substituted dienes towards the reactive non-quinonoid dienophile tetracyanoethylene.