1-(3-(tert-butyldimethylsilyloxy)buta-1,3-dienyl)-1H-pyrazole | 958669-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-(tert-butyldimethylsilyloxy)buta-1,3-dienyl)-1H-pyrazole
• 英文别名: tert-butyl-dimethyl-[(3E)-4-pyrazol-1-ylbuta-1,3-dien-2-yl]oxysilane
• CAS: 958669-96-0
• 化学式: C₁₃H₂₂N₂OSi
• 分子量: 250.416
• InChiKey: PLQLZJIJWAGJRT-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-(tert-butyldimethylsilyloxy)buta-1,3-dienyl)-1H-pyrazole 、 methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate 以 二氯甲烷 为溶剂， 反应 17.0h， 以55%的产率得到methyl 4-(tert-butyldimethylsilyloxy)-7-(p-tolyl)-2-(1H-pyrazol-1-yl)-1-aza-bicyclo[4.1.0]hept-3-ene-6-carboxylate
  参考文献：
  名称：

  Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-aza-bicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride

  摘要：

  Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R-1 is an oxycarbonyl or a 2-pyridyl group and R-2 is a negative charge-stabilizing group (cases 3a,b and 4f) the C-C bond cleaves forming products 5. However, when R-2 = H (case 3c) the ring expands to seven members. When R1 is an acyl group the pyridin-4(1H)-one formation includes an unexpected shift of the carbonyl group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.007
• 作为产物：
  描述：

  4-(1H-pyrazol-1-yl)but-3-en-2-one 、 叔丁基二甲基氯硅烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98.6%的产率得到1-(3-(tert-butyldimethylsilyloxy)buta-1,3-dienyl)-1H-pyrazole
  参考文献：
  名称：

  Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-aza-bicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride

  摘要：

  Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R-1 is an oxycarbonyl or a 2-pyridyl group and R-2 is a negative charge-stabilizing group (cases 3a,b and 4f) the C-C bond cleaves forming products 5. However, when R-2 = H (case 3c) the ring expands to seven members. When R1 is an acyl group the pyridin-4(1H)-one formation includes an unexpected shift of the carbonyl group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.007