5,5-di(azidomethyl)-2-phenyl-1,3-dioxane | 104274-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 5,5-di(azidomethyl)-2-phenyl-1,3-dioxane
• 英文别名: [OA-1-107]；5,5-bis(azidomethyl)-2-phenyl-1,3-dioxane
• CAS: 104274-83-1
• 化学式: C₁₂H₁₄N₆O₂
• 分子量: 274.282
• InChiKey: CTLKIBPTYXTPKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5-di(azidomethyl)-2-phenyl-1,3-dioxane 生成 5,5-Bis-(aminomethyl)-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  KOLAR, C.;KRAEMER, H. P.;DEHMEL, K.

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 1,3-丙二醇,2,2-二(叠氮甲基)- 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到5,5-di(azidomethyl)-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

  摘要：

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.

  DOI：

  10.1021/ol101645k

文献信息

• KOLAR, C.;KRAEMER, H. P.;DEHMEL, K.
  作者：KOLAR, C.、KRAEMER, H. P.、DEHMEL, K.

  DOI：——

  日期：——
• Cis-Platin-Komplexe mit einem Pentaerythritderivat als Liganden, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltendes pharmazeutisches Mittel
  申请人：BEHRINGWERKE Aktiengesellschaft

  公开号：EP0174542B1

  公开（公告）日：1989-06-28
• US4730069A
  申请人：——

  公开号：US4730069A

  公开（公告）日：1988-03-08
• “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors
  作者：Oyebola A. Oladeinde、Sam Y. Hong、Ryan J. Holland、Anna E. Maciag、Larry K. Keefer、Joseph E. Saavedra、Rahul S. Nandurdikar

  DOI：10.1021/ol101645k

  日期：2010.10.1

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.