(1S,2R,3S,8R)-4,4-dimethyl-3-nitro-9,11-dioxatricyclo[6.2.1.0^2,6]undec-5-en-7-one | 676438-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (1S,2R,3S,8R)-4,4-dimethyl-3-nitro-9,11-dioxatricyclo[6.2.1.0^2,6]undec-5-en-7-one
• 英文别名: (1s,2r,3s,8r)-4,4-Dimethyl-3-nitro-9,11-dioxa-tricyclo[6,2,1,0 2,6]undec-5-en-7-one；(1S,2R,3S,8R)-4,4-dimethyl-3-nitro-9,11-dioxatricyclo[6.2.1.02,6]undec-5-en-7-one
• CAS: 676438-29-2
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: SOWHLMOXOZPBFZ-GOZTYBTRSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-丁二烯 、 (1S,2R,3S,8R)-4,4-dimethyl-3-nitro-9,11-dioxatricyclo[6.2.1.0^2,6]undec-5-en-7-one 以 甲苯 为溶剂， 反应 4.0h， 生成 (1S,2R,3S,5R,10R,12R)-4,4-dimethyl-3-nitro-13,15-dioxatetracyclo[7.5.1.0.0^2,10]pentadec-7-en-11-one
  参考文献：
  名称：

  Cyclopentane Ring Fusion to  -Iodo and  -Bromo Levoglucosenone Derivatives with 2,2-Dimethyl-1,3-dinitropropane

  摘要：

  DOI：

  10.1023/b:rujo.0000003205.64908.dd
• 作为产物：
  描述：

  左旋葡萄糖酮 在 吡啶 、 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (1S,2R,3S,8R)-4,4-dimethyl-3-nitro-9,11-dioxatricyclo[6.2.1.0^2,6]undec-5-en-7-one
  参考文献：
  名称：

  Reaction of nitroalkanes with levoglucosenone and its α-bromo and α-iodo derivatives. Cyclopentaannulation of α-halocyclenones

  摘要：

  Michael reactions of levoglucosenone and its alpha-bromo and alpha-iodo derivatives with alpha,omega-dinitroalkanes were studied under conditions of chemical and electrochemical generation of base. Procedures were developed for stereospecific fusion of a cyclopentane ring to alpha-bromo- and alpha-iodolevoglucosenones, 2-iodocyclopent-2-en-1-one, and 2-iodocyclohex-2-en-1-one by the action of 2,2-dimethyl-1,3-dinitropropane.

  DOI：

  10.1134/s1070428011060145

文献信息

• Opening of the 1,6-anhydro bridge with selective reduction of the acetal moiety in levoglucosenone and its derivatives
  作者：A. R. Tagirov、I. M. Biktagirov、Yu. S. Galimova、L. Kh. Faizullina、Sh. M. Salikhov、F. A. Valeev

  DOI：10.1134/s1070428015040181

  日期：2015.4

  Treatment of levoglucosenone and some its derivatives with chloro(trimethyl)silane and sodium iodide in acetonitrile leads to opening of the 1,6-anhydro bridge and simultaneous reduction of the pyranose ring to pyran.