Ethyl 3-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxy-2-diazopropanoate | 928834-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 3-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxy-2-diazopropanoate
• 英文别名: ethyl 3-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxy-2-diazopropanoate
• CAS: 928834-54-2
• 化学式: C₂₇H₂₉BrN₂O₃Si
• 分子量: 537.528
• InChiKey: KXQLWIVLJQIZEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxy-2-diazopropanoate 在 dirhodium tetraacetate silica gel 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到ethyl (Z)-2-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxyprop-2-enoate
  参考文献：
  名称：

  DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

  摘要：

  DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding beta-hydroxy alpha-diazo carbonyl compounds. The beta-hydroxy group of the products was further converted into beta-siloxy group. The Rh(II)-catalyzed reaction of the beta-aryl beta-siloxy alpha-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl beta-hydroxy alpha-arylacrylates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.062
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 ethyl-2-diazo-3-hydroxy-3-(3-bromophenyl)-propanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 Ethyl 3-(3-bromophenyl)-3-[tert-butyl(diphenyl)silyl]oxy-2-diazopropanoate
  参考文献：
  名称：

  DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

  摘要：

  DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding beta-hydroxy alpha-diazo carbonyl compounds. The beta-hydroxy group of the products was further converted into beta-siloxy group. The Rh(II)-catalyzed reaction of the beta-aryl beta-siloxy alpha-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl beta-hydroxy alpha-arylacrylates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.062

文献信息

• DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates
  作者：Fengping Xiao、Yu Liu、Jianbo Wang

  DOI：10.1016/j.tetlet.2006.12.062

  日期：2007.2

  DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding beta-hydroxy alpha-diazo carbonyl compounds. The beta-hydroxy group of the products was further converted into beta-siloxy group. The Rh(II)-catalyzed reaction of the beta-aryl beta-siloxy alpha-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl beta-hydroxy alpha-arylacrylates. (c) 2006 Elsevier Ltd. All rights reserved.