3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,6-dimethyl-5-prop-1-en-2-ylhept-5-enamide | 273380-85-1

• 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: 3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,6-dimethyl-5-prop-1-en-2-ylhept-5-enamide
• CAS: 273380-85-1
• 化学式: C₁₉H₃₇NO₃Si
• 分子量: 355.593
• InChiKey: VJBQQMZZIVEVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,6-dimethyl-5-prop-1-en-2-ylhept-5-enamide 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成
  参考文献：
  名称：

  Progress towards an intramolecular Diels–Alder ring-expansion approach to taxinine: the interplay of Lewis acids and high pressure

  摘要：

  A concise route to a bicyclo[4.2.1] ring system, based on an intramolecular Diels-Alder reaction, has been developed. Preliminary results on the interplay between Lewis acids and high pressure to facilitate the reaction are described. Products with isomerized double bonds were obtained with 1 equivalent of Lewis acid at 0 degrees C. The stereochemistry of these compounds has been determined by X-ray crystallography. Double bond isomerization is suppressed by the use of excess Lewis acid at -78 degrees C or high pressure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00248-3
• 作为产物：
  描述：

  3-isopropenyl-4-methyl-pent-3-en-1-ol 在 咪唑 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 3-[tert-butyl(dimethyl)silyl]oxy-N-methoxy-N,6-dimethyl-5-prop-1-en-2-ylhept-5-enamide
  参考文献：
  名称：

  Progress towards an intramolecular Diels–Alder ring-expansion approach to taxinine: the interplay of Lewis acids and high pressure

  摘要：

  A concise route to a bicyclo[4.2.1] ring system, based on an intramolecular Diels-Alder reaction, has been developed. Preliminary results on the interplay between Lewis acids and high pressure to facilitate the reaction are described. Products with isomerized double bonds were obtained with 1 equivalent of Lewis acid at 0 degrees C. The stereochemistry of these compounds has been determined by X-ray crystallography. Double bond isomerization is suppressed by the use of excess Lewis acid at -78 degrees C or high pressure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00248-3

文献信息

• Progress towards an intramolecular Diels–Alder ring-expansion approach to taxinine: the interplay of Lewis acids and high pressure
  作者：Andrew J. Phillips、Jonathan C. Morris、Andrew D. Abell

  DOI：10.1016/s0040-4039(00)00248-3

  日期：2000.4

  A concise route to a bicyclo[4.2.1] ring system, based on an intramolecular Diels-Alder reaction, has been developed. Preliminary results on the interplay between Lewis acids and high pressure to facilitate the reaction are described. Products with isomerized double bonds were obtained with 1 equivalent of Lewis acid at 0 degrees C. The stereochemistry of these compounds has been determined by X-ray crystallography. Double bond isomerization is suppressed by the use of excess Lewis acid at -78 degrees C or high pressure. (C) 2000 Elsevier Science Ltd. All rights reserved.