7,9-bis[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-8-azaspiro[4.5]deca-6,9-diene | 854280-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 7,9-bis[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-8-azaspiro[4.5]deca-6,9-diene
• 英文别名: Tert-butyl 7,9-bis[[oxido(diphenoxy)phosphaniumyl]oxy]-8-azaspiro[4.5]deca-6,9-diene-8-carboxylate
• CAS: 854280-08-3
• 化学式: C₃₈H₃₉NO₁₀P₂
• 分子量: 731.676
• InChiKey: MTSOJNCNBCWFEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7,9-bis[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-8-azaspiro[4.5]deca-6,9-diene 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 3.0h， 以85%的产率得到8-(tert-butoxycarbonyl)-7,9-diphenyl-8-azaspiro[4.5]deca-6,9-diene
  参考文献：
  名称：

  Reactivity of bis-vinylphosphates obtained from imide derivatives. Synthesis of 2,6-disubstituted 1,4-dihydropyridines

  摘要：

  The Pd-catalyzed functionalization of lactam-derived vinyl phosphates has become an important tool in the last decade for the synthesis of nitrogen-containing heterocycles. By using this method, we were able to introduce alkenyl, aryl and heteroaryl groups on bis-vinylphosphate derivatives to provide efficient access to 2,6-disubstituted 1,4-dihydropyridines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.136
• 作为产物：
  描述：

  3,3-四亚甲基戊二酰亚胺 在 4-二甲氨基吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 32.0h， 生成 7,9-bis[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-8-azaspiro[4.5]deca-6,9-diene
  参考文献：
  名称：

  Reactivity of bis-vinylphosphates obtained from imide derivatives. Synthesis of 2,6-disubstituted 1,4-dihydropyridines

  摘要：

  The Pd-catalyzed functionalization of lactam-derived vinyl phosphates has become an important tool in the last decade for the synthesis of nitrogen-containing heterocycles. By using this method, we were able to introduce alkenyl, aryl and heteroaryl groups on bis-vinylphosphate derivatives to provide efficient access to 2,6-disubstituted 1,4-dihydropyridines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.136

文献信息

• Synthesis and Reactivity of Imide-Derived Bisvinyl Phosphates. Reactivity of 2,6-Disubstituted 1,4-Dihydropyridines
  作者：Deborah Mousset、Isabelle Gillaizeau、Andréa Sabatié,、Pascal Bouyssou、Gérard Coudert

  DOI：10.1021/jo0607360

  日期：2006.8.1

  Symmetrical and unsymmetrical 2,6-disubstituted dihydropyridines were prepared in high yields under mild conditions using the Suzuki and Stille Pd-catalyzed coupling reactions of imide-derived bisvinyl phosphates with a range of aryl, heteroaryl, and alkenyl moieties. The alkylation reaction at C-4 easily afforded original tri- and tetrasubstituted dihydropyridines. Hydrolysis of the latter under acidic condition provided efficiently either open-chain 1,5-diketones or di- or trisubstituted pyridines.