cis-2-carboxy-2,5-dimethyl-5-nitro-1,3-dioxane | 562081-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-carboxy-2,5-dimethyl-5-nitro-1,3-dioxane
• CAS: 562081-76-9
• 化学式: C₇H₁₁NO₆
• 分子量: 205.167
• InChiKey: ZNMMPYXJJBSLMP-KNVOCYPGSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  364.7±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-2-carboxy-2,5-dimethyl-5-nitro-1,3-dioxane 在 dirhodium tetraacetate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 36.08h， 生成 (1R,4S,5S)-1,4-Dimethyl-4-nitro-2,8-dioxa-bicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Template-directed CH activation: development and application to the total synthesis of 7-episordidin

  摘要：

  The development of a template-directed C-H activation strategy and its application to the diastereoselective synthesis of (+/-)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of the synthetic route is a regioselective rhodium(II)-catalyzed diazocarbonyl C-H activation reaction that simultaneously generates three of the four stereocenters present in the natural product. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00091-0
• 作为产物：
  描述：

  cis-2-methoxycarbonyl-2,5-dimethyl-5-nitro-1,3-dioxane 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以99%的产率得到cis-2-carboxy-2,5-dimethyl-5-nitro-1,3-dioxane
  参考文献：
  名称：

  Template-directed CH activation: development and application to the total synthesis of 7-episordidin

  摘要：

  The development of a template-directed C-H activation strategy and its application to the diastereoselective synthesis of (+/-)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of the synthetic route is a regioselective rhodium(II)-catalyzed diazocarbonyl C-H activation reaction that simultaneously generates three of the four stereocenters present in the natural product. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00091-0