(+/-)-6-oxobicyclo<2.2.1>heptane-endo-2-carboxylic acid | 42392-37-0

• 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: (+/-)-6-oxobicyclo<2.2.1>heptane-endo-2-carboxylic acid
• 英文别名: 6-oxo-bicyclo<2.2.1>heptane-endo-2-carboxylic acid；6-Oxobicyclo<2.2.1>heptane-2-endo-carboxylic acid；(+/-)-bicyclo[2.2.1]heptan-6-one-2-endo-carboxylic acid；endo-2-carboxybicyclo[2.2.1]heptan-2-one；6-oxonorbornane-2-endo-carboxylic acid；6-Oxo-bicyclo<2.2.1>heptan-endo-2-carbonsaeure；rac-(1R,2S,4S)-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid；(1S,2R,4R)-6-oxobicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 42392-37-0
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: RUOYCLYBCGDWPG-NGJCXOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-6-oxobicyclo<2.2.1>heptane-endo-2-carboxylic acid 在 盐酸 、 lithium aluminium tetrahydride 、 硼氘化钠 、 pyridinium hydrobromide perbromide 、 对甲苯磺酸 作用下， 以 吡啶 、 乙醚 、 溶剂黄146 、 异丙醇 、 苯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Photochemistry of alkyl halides. 8. Formation of a bridgehead alkene

  摘要：

  DOI：

  10.1021/ja00378a033
• 作为产物：
  描述：

  endo-2-Carboxy-exo-3-carboxy-6-keto-norbornan 在 sodium hydroxide 作用下， 生成 (+/-)-6-oxobicyclo<2.2.1>heptane-endo-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of endo-2-Carboxy-endo-6-aminonorbornane Lactam¹

  摘要：

  DOI：

  10.1021/jo01070a530

文献信息

• Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction
  作者：Urs D. Wermuth、Ian D. Jenkins、Raymond C. Bott、Karl A. Byriel、Graham Smith

  DOI：10.1071/ch03202

  日期：——

  Both the Strecker and Bucherer–Bergs reactions convert the norbornane keto ester methyl bicyclo[2.2.1]hept-6-one-2-endo-carboxylate into the lactam 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylic acid-γ-lactam-6-exo-carboxylic acid. This lactam is unusually stable and cannot be hydrolyzed to the corresponding amino acid. The stereochemistry in the Strecker reaction, in which the amino group is

  Strecker 和 Bucherer-Bergs 反应均将降冰片烷酮酯甲酯双环[2.2.1]hept-6-one-2-endo-carboxylate 转化为内酰胺 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylate羧酸-γ-内酰胺-6-外-羧酸。这种内酰胺异常稳定，不能水解成相应的氨基酸。Strecker 反应中的立体化学（其中氨基为内基）与文献先例所预期的相反。Bucherer-Bergs 反应中的立体化学，其中氨基也是 endo，已通过中间体螺乙内酰脲 (±)-bicyclo[2.2.1]heptane-2-endo-carboxy acid- 的 X 射线晶体学分析得到证实。 6-螺-5'-乙内酰脲。
• Oxidation of γ-Lactones to γ-Oxocarboxylic Acids at the Nickel Hydroxide Electrode
  作者：Heinrich Ruholl、Hans -J. Schäfer

  DOI：10.1055/s-1987-27966

  日期：——

  γ-Lactones are oxidized to γ-oxocarboxylic acids with excellent yields by electrolysis at an oxide covered nickel-net electrode in an aqueous alkaline electrolyte and an undivided cell.

  γ-内酯在铝氧化镍网电极的水性碱性电解液中以优异的产率被电解氧化为γ-氧代羧酸，且采用未分隔的电池。
• Michaelis, Ralf; Mueller, Ulrich; Schaefer, Hans J., Angewandte Chemie, 1987, vol. 99, # 10, p. 1049 - 1050
  作者：Michaelis, Ralf、Mueller, Ulrich、Schaefer, Hans J.

  DOI：——

  日期：——
• Monoamine oxidase-catalyzed oxidation of endo,endo -2-amino-6-[( Z )-2′-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate
  作者：Xueqing Wang、Richard B Silverman

  DOI：10.1016/s0968-0896(00)00094-8

  日期：2000.7

  An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and photophysical properties of some endo-6-substituted norcamphors and pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-ones
  作者：Ronald R. Sauers、Michael Zampino、Michael Stockl、Jill Ferentz、Hoda Shams

  DOI：10.1021/jo00159a013

  日期：1983.6