(-)-Benzyl (1S,4R)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

• 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: (-)-Benzyl (1S,4R)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
• 英文别名: benzyl 2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate；benzyl (1S,4R)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: UPKIPGGUNYLFTM-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-环己二烯 在 5-O-Acetyl-2,3-O-isopropylidene-1-C-nitroso-D-ribofuranosyl 、 sodium carbonate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 27.0h， 生成 (-)-Benzyl (1S,4R)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
  参考文献：
  名称：

  Enantioselective Diels-Alder Reaction with an α-Chloronitrose Dienophile Derived from 5-O-Acetyl-2,3-isopropylidenedioxy-d-ribose

  摘要：

  晶体形式的5-O-乙酰基-2,3-异丙基二氧基-d-核糖内酯肟（8）通过从d-核糖合成，整体产率为40%。氯亚硝基二烯亲电试剂3b是通过t-BuOCl氧化8得到的，并与环状和非环状二烯10-13进行了不对称Diels-Alder反应，生成了晶体加合物14a-17a，产率良好且光学纯度极高（93-99%）。

  DOI：

  10.1055/s-2000-8214

文献信息

• Accessing nitrosocarbonyl compounds with temporal and spatial control via the photoredox oxidation of N-substituted hydroxylamines
  作者：Charles P. Frazier、Leoni I. Palmer、Andrey V. Samoshin、Javier Read de Alaniz

  DOI：10.1016/j.tetlet.2015.01.024

  日期：2015.6

  Photoredox catalysis is employed to generate highly reactive acylnitroso species from hydroxamic acid derivatives. The conditions are shown to be comparable to a previously developed transition metal aerobic oxidation and are amenable to a range of transformations including Diels-Alder and ene reactions. This unique application of such an approach gives access to temporal and spatial control in nitroso chemistry. Published by Elsevier Ltd.
• Enantioselective Diels-Alder Reaction with an α-Chloronitrose Dienophile Derived from 5-O-Acetyl-2,3-isopropylidenedioxy-d-ribose
  作者：Albert Defoin、Muriel Joubert、Jean-Marc Heuchel、Christiane Strehler、Jacques Streith

  DOI：10.1055/s-2000-8214

  日期：——

  Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-d-ribonolactone oxime (8) was synthesised from d-ribose in 40% overall yield. The chloronitroso dienophile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetric Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crystalline adducts 14a-17a in good yield and excellent enantiomeric excess (93-99%).

  晶体形式的5-O-乙酰基-2,3-异丙基二氧基-d-核糖内酯肟（8）通过从d-核糖合成，整体产率为40%。氯亚硝基二烯亲电试剂3b是通过t-BuOCl氧化8得到的，并与环状和非环状二烯10-13进行了不对称Diels-Alder反应，生成了晶体加合物14a-17a，产率良好且光学纯度极高（93-99%）。