2-exo,3-exo-diacetoxymethyl-bicyclo[2.2.1]heptane | 142438-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-exo,3-exo-diacetoxymethyl-bicyclo[2.2.1]heptane
• 英文别名: bicyclo<2.2.1>heptane-exo-2,exo-3-dimethanol diacetate；2-exo,3-exo-bis(acetoxymethyl)bicyclo[2.2.1]heptane；[(1S,2R,3S,4R)-3-(acetyloxymethyl)-2-bicyclo[2.2.1]heptanyl]methyl acetate
• CAS: 142438-49-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: DNBMMUAYISKAFV-FNFFVJSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  bicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol diacetate 在 肼-D4 、 氧气 、 5-ethyl-3-methyllumiflavinium perchlorate 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以93%的产率得到2-exo,3-exo-diacetoxymethyl-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Flavin-Catalyzed Generation of Diimide:  An Environmentally Friendly Method for the Aerobic Hydrogenation of Olefins

  摘要：

  The first green and practical method for "aerobic hydrogenation" involving the use of hydrazine and an organocatalyst is described. Olefins can be hydrogenated by treatment with hydrazine in the presence of a 5-ethyl-3-methyllumiflavinium perchlorate (FlEt+.ClO4-) catalyst under O2 atmosphere to give the corresponding hydrogenated products in excellent yields along with environmentally benign water and molecular nitrogen as the only waste products.

  DOI：

  10.1021/ja053976q

文献信息

• Neutral Flavins: Green and Robust Organocatalysts for Aerobic Hydrogenation of Olefins
  作者：Yasushi Imada、Takahiro Kitagawa、Takashi Ohno、Hiroki Iida、Takeshi Naota

  DOI：10.1021/ol902393p

  日期：2010.1.1

  Various olefins can be hydrogenated quantitatively with neutral flavin 2 catalysts in the presence of 1-2 equiv of hydrazine under 1 atm of O(2), Vitamin B(2) derivative 2g acts as a highly efficient and robust catalyst for the present environmentally benign process producing water and nitrogen gas as the only waste products.