N-benzyloxycarbonyl-1-methyl-2-azaadamantane | 872598-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxycarbonyl-1-methyl-2-azaadamantane
• 英文别名: Benzyl 1-methyl-2-azaadamantane-2-carboxylate；benzyl 1-methyl-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate
• CAS: 872598-46-4
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: ANFBLKKERMLHED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-1-methyl-2-azaadamantane 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-甲基-2-氮杂金刚烷
  参考文献：
  名称：

  EP1775296

  摘要：

  公开号：
• 作为产物：
  描述：

  benzyl (7-methylene-bicyclo[3.3.1]non-3-yl)carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以100%的产率得到N-benzyloxycarbonyl-1-methyl-2-azaadamantane
  参考文献：
  名称：

  EP1775296

  摘要：

  公开号：

文献信息

• Alcohol Oxidation Catalyst and Method of Synthesizing the Same
  申请人：Iwabuchi Yoshiharu

  公开号：US20070232838A1

  公开（公告）日：2007-10-04

  An organic oxidation catalyst for alcohols which is environmentally less harmful and with which efficient oxidation can be conducted. The oxidation catalyst for alcohols is a 1-alkyl-2-azadamantan-N-oxyl which has a nitroxyl group incorporated in the adamantane skeleton and was synthesized from as a base material a bicyclic compound obtained by the Grob-type ring-opening reaction of 1,3-adamantanediol. Due to the nitroxyl group on the adamantane skeleton, the α-position hydrogen is stabilized based on Bredt's rule and the stability of the oxoammonium group generated by the oxidation thereof is ensured. Compared to TEMPO, which is a conventional oxidation catalyst, this catalyst is reduced in steric hindrance and is usable in a wide range of reaction fields. Because of this, not only a primary alcohol but a secondary alcohol having a sterically complicated structure, which has been difficult to oxidize with TEMPO, can be oxidized at a high efficiency.

  这是一种对醇类进行高效氧化且环境友好的有机氧化催化剂。该醇类氧化催化剂是一种含有亚胺氧基的1-烷基-2-氮杂双环[10.2.1]戊烷-N-氧化物，其亚胺氧基嵌入了双环戊烷骨架中，并以1,3-戊二醇的Grob型开环反应产物为基础材料合成而成。由于双环戊烷骨架上的亚胺氧基，根据Bredt规则，α-位置的氢被稳定，确保氧化后生成的氧羟铵基团的稳定性。与传统氧化催化剂TEMPO相比，这种催化剂的立体位阻更小，可用于广泛的反应领域。因此，不仅可以高效地氧化一级醇，还可以氧化二级醇，即使其具有立体构型复杂的结构，在TEMPO中也难以氧化。
• ALCOHOL OXIDATION CATALYST AND METHOD OF SYNTHESIZING THE SAME
  申请人：TOHOKU UNIVERSITY

  公开号：EP1775296A1

  公开（公告）日：2007-04-18

  An organic oxidation catalyst for alcohols which is environmentally less harmful and with which efficient oxidation can be conducted. The oxidation catalyst for alcohols is a 1-alkyl-2-azadamantan-N-oxyl which has a nitroxyl group incorporated in the adamantane skeleton and was synthesized from as a base material a bicyclic compound obtained by the Grob-type ring-opening reaction of 1,3-adamantanediol. Due to the nitroxyl group on the adamantane skeleton, the α-position hydrogen is stabilized based on Bredt's rule and the stability of the oxoammonium group generated by the oxidation thereof is ensured. Compared to TEMPO, which is a conventional oxidation catalyst, this catalyst is reduced in steric hindrance and is usable in a wide range of reaction fields. Because of this, not only a primary alcohol but a secondary alcohol having a sterically complicated structure, which has been difficult to oxidize with TEMPO, can be oxidized at a high efficiency.

  一种对环境危害较小并能进行高效氧化的有机醇类氧化催化剂。这种醇类氧化催化剂是一种 1-烷基-2-氮杂金刚烷-N-氧代物，它的金刚烷骨架上含有一个亚硝基，是以 1,3-金刚烷二醇通过格劳博型开环反应得到的双环化合物为基料合成的。由于金刚烷骨架上含有硝基，根据布雷特法则，α 位氢得以稳定，并确保了由其氧化产生的氧氨基团的稳定性。与传统氧化催化剂 TEMPO 相比，该催化剂的立体阻碍减少，可用于广泛的反应领域。因此，不仅是伯醇，就连 TEMPO 难以氧化的立体结构复杂的仲醇也能高效氧化。
• EP1775296
  申请人：——

  公开号：——

  公开（公告）日：——