(1S)-7,7-dimethyl-2,3-dioxobicyclo<2.2.1>heptane-1-carboxylic acid | 82480-28-2

• 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: (1S)-7,7-dimethyl-2,3-dioxobicyclo<2.2.1>heptane-1-carboxylic acid
• 英文别名: (1S)-7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid；(1S,4S)-7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid
• CAS: 82480-28-2
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: IUDWGHRBQRGLDJ-FWOIEVBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-7,7-dimethyl-2,3-dioxobicyclo<2.2.1>heptane-1-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以77%的产率得到(1R,2S,3R)-1-(hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptane-2,3-diol
  参考文献：
  名称：

  Stereocontrolled synthesis of conformationally restricted enantiopure triols and dihydroxy acids based on the norbornane framework

  摘要：

  The synthesis of chiral, rigid analogues of glycerol and cyclitols has been achieved by means of the stereocontrolled reduction of chiral bridgehead-Substituted camphorquinones. This simple and easy procedure exclusively affords dillydroxy derivatives with a 2,3-cis-exo-configuration. The employment of different hydrides has also allowed the synthesis of enantiopure 2,3-dillydroxy carboxylic acids with high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.001
• 作为产物：
  描述：

  (S)-(+)-酮基蒎酸 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 以87%的产率得到(1S)-7,7-dimethyl-2,3-dioxobicyclo<2.2.1>heptane-1-carboxylic acid
  参考文献：
  名称：

  （1 R）-N-亚硝基-1-氘代Apophophaidine的合成及圆二色性

  摘要：

  标题化合物（1）的cd光谱与（1 R）-N-亚硝基羰基吡啶（2）的cd光谱的比较表明，氘代基团对棉效应有显着贡献。

  DOI：

  10.1039/c39820000208

文献信息

• Synthesis and circular dichroism of (1R)-N-nitroso-1-deuterioapocamphidine
  作者：Tadeusz Połoński

  DOI：10.1039/c39820000208

  日期：——

  Comparison of the c.d. spectrum of the title compound (1) with that of (1R)-N-nitrosocamphidine (2) shows that the deuterium substitutent makes a dissignate contribution to the Cotton effect.

  标题化合物（1）的cd光谱与（1 R）-N-亚硝基羰基吡啶（2）的cd光谱的比较表明，氘代基团对棉效应有显着贡献。
• Polonski, Tadeusz, Journal of the Chemical Society. Perkin transactions I, 1983, p. 305 - 310
  作者：Polonski, Tadeusz

  DOI：——

  日期：——
• Polonski, Tadeusz; Dauter, Zbigniew, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1781 - 1788
  作者：Polonski, Tadeusz、Dauter, Zbigniew

  DOI：——

  日期：——
• Stereocontrolled synthesis of conformationally restricted enantiopure triols and dihydroxy acids based on the norbornane framework
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Amelia Garcı́a Fraile、Paloma Martı́nez-Ruiz

  DOI：10.1016/j.tetasy.2005.06.001

  日期：2005.7

  The synthesis of chiral, rigid analogues of glycerol and cyclitols has been achieved by means of the stereocontrolled reduction of chiral bridgehead-Substituted camphorquinones. This simple and easy procedure exclusively affords dillydroxy derivatives with a 2,3-cis-exo-configuration. The employment of different hydrides has also allowed the synthesis of enantiopure 2,3-dillydroxy carboxylic acids with high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• New route to amide-functionalized N-donor ligands enables improved selective solvent extraction of trivalent actinides
  作者：Rachel Bulmer、Thomas B. Spencer、Andreas Wilden、Giuseppe Modolo、Trong-Hung Vu、Jean-Pierre Simonin、Frank W. Lewis

  DOI：10.1039/d2cc03876e

  日期：——

  established. The amide-functionalized ligands separate Am(III) and Cm(III) from the lanthanides with high selectivities and show rapid rates of metal extraction. The ligands retain the advantages of the analogous unfunctionalized ligands derived from camphorquinone, whilst also negating their main drawback; precipitate formation when in contact with nitric acid. These studies could enable the design of

  建立了用于乏核燃料后处理的选择性锕系元素提取配体的新通用合成路线。酰胺官能化配体以高选择性将 Am( III ) 和 Cm( III ) 从镧系元素中分离出来，并显示出快速的金属萃取率。该配体保留了衍生自樟脑醌的类似非官能化配体的优点，同时也消除了它们的主要缺点；与硝酸接触时形成沉淀。这些研究可以设计用于关闭核燃料循环的改进的溶剂萃取工艺。