Methyl 3,3-dimethyl-9-oxo-2,4-dioxaspiro[5.5]undecane-10-carboxylate | 1441985-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3,3-dimethyl-9-oxo-2,4-dioxaspiro[5.5]undecane-10-carboxylate
• 英文别名: methyl 3,3-dimethyl-9-oxo-2,4-dioxaspiro[5.5]undecane-10-carboxylate
• CAS: 1441985-08-5
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: UQGOYFOBHVVQHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3,3-dimethyl-9-oxo-2,4-dioxaspiro[5.5]undecane-10-carboxylate 在 iron(III) chloride hexahydrate 、 四氯化钛 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 8.17h， 生成
  参考文献：
  名称：

  PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine

  摘要：

  A synthetic strategy for the modeling construction of the A/E/F ring system of lycoctonine-type C-19-diterpenoid alkaloids bearing a featuring oxygen functional group at C-7 has been successfully developed. The key steps involved a diastereoselective gold(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA-promoted intramolecular transannular aziridination followed by regioselective ring cleavage to give the azatricyclic amine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.102
• 作为产物：
  描述：

  2,2-bis(3-methoxy-3-oxopropyl)malonic acid 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.5h， 生成 Methyl 3,3-dimethyl-9-oxo-2,4-dioxaspiro[5.5]undecane-10-carboxylate
  参考文献：
  名称：

  PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine

  摘要：

  A synthetic strategy for the modeling construction of the A/E/F ring system of lycoctonine-type C-19-diterpenoid alkaloids bearing a featuring oxygen functional group at C-7 has been successfully developed. The key steps involved a diastereoselective gold(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA-promoted intramolecular transannular aziridination followed by regioselective ring cleavage to give the azatricyclic amine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.102

文献信息

• PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine
  作者：Zhi-Gang Liu、Hang Cheng、Meng-Jia Ge、Liang Xu、Feng-Peng Wang

  DOI：10.1016/j.tet.2013.04.102

  日期：2013.7

  A synthetic strategy for the modeling construction of the A/E/F ring system of lycoctonine-type C-19-diterpenoid alkaloids bearing a featuring oxygen functional group at C-7 has been successfully developed. The key steps involved a diastereoselective gold(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA-promoted intramolecular transannular aziridination followed by regioselective ring cleavage to give the azatricyclic amine. (C) 2013 Elsevier Ltd. All rights reserved.