3-cyano-1,2,2-trimethylcyclopentanecarboxylic acid | 13792-51-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-cyano-1,2,2-trimethylcyclopentanecarboxylic acid
• 英文别名: 3-cyano-1,2,2-trimethyl-cyclopentanecarboxylic acid；3-Cyan-1,2,2-trimethyl-cyclopentancarbonsaeure；α-Camphernitril-saeure；(+/-)-Camphersaeure-3-nitril；3-Cyano-1,2,2-trimethylcyclopentane-1-carboxylic acid
• CAS: 13792-51-3；57793-95-0
• 化学式: C₁₀H₁₅NO₂
• mdl: MFCD09754271
• 分子量: 181.235
• InChiKey: MPVYPDDIWQUOEU-UHFFFAOYSA-N

物化性质

• 沸点：
  320.3±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-1,2,2-trimethylcyclopentanecarboxylic acid 在 正辛烷 、 五氯化磷 作用下， 生成 3-cyano-1,2,2-trimethyl-cyclopentanecarbonyl chloride
  参考文献：
  名称：

  Bredt; Iwanoff, Chemische Berichte, 1925, vol. 58, p. 60

  摘要：

  DOI：
• 作为产物：
  描述：

  樟脑醌 在 吡啶 、 盐酸羟胺 、 对甲苯磺酰氯 作用下， 以 氢氧化钾 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 3-cyano-1,2,2-trimethylcyclopentanecarboxylic acid
  参考文献：
  名称：

  Vaidya, S. P.; Shitole, H. R.; Nayak, U. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 36 - 39

  摘要：

  DOI：

文献信息

• Perrhenic Acid-Catalyzed Dehydration from Primary Amides, Aldoximes,<i>N</i>-Monoacylureas, and α-Substituted Ketoximes to Nitrile Compounds
  作者：Yoshiro Furuya、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1246/bcsj.80.400

  日期：2007.1.15

  The dehydration reaction of primary amides is one of the most fundamental methods for the synthesis of nitriles, and the development of environmentally benign catalytic reaction processes is needed. We surveyed a variety of metal catalysts and found that perrhenic acid was extremely effective for the dehydration of not only primary amides but also aldoximes. Typically, 1 mol % of perrhenic acid gave

  伯酰胺的脱水反应是合成腈类最基本的方法之一，需要开发环境友好的催化反应工艺。我们调查了各种金属催化剂，发现高铼酸不仅对伯酰胺而且对醛肟的脱水都非常有效。通常，在共沸回流条件下，在甲苯或均三甲苯中除去水，1 mol%的高铼酸由酰胺或醛肟得到相应的腈。此外，高铼酸是一种非常有效的催化剂，用于将 α-取代的酮肟贝克曼裂解成官能化的腈。这种新的催化系统无需进一步修改即可应用于腈的克级合成。
• Tuning structure and properties of Pd and Pt camphor derived complexes
  作者：Ana S.D. Ferreira、M. Fernanda N.N. Carvalho、Adelino M. Galvão、Luís F. Veiros

  DOI：10.1016/j.ica.2012.10.036

  日期：2013.1

  Seven new camphor palladium or platinum compounds with novel metal coordination environments were obtained by convenient choice of the experimental conditions in particular the solvent. cis-[PtCl2(PhNC10 H14O)(2)]) and [Pd(MeNNC10H14O)(2)] were structurally characterized by X-ray diffraction analysis while [PtCl2(Me2NC10H13NSO2)}(2)], [PdCl2(YNC10H14O)}(2)] (Y = NMe2, NPh2) and [Pd(PhNNC10H14O)(2)] were formulated by elemental analysis and spectroscopic techniques. Relevant aspects of the IR and NMR spectra of complexes [Pd(YNC10H14O)(2)] (Y = MeN, PhN) are discussed with the help of DFT calculations. Evaluation of the properties of the new complexes as catalysts for activation of 4-pentyn-1-ol towards formation of cyclization products showed that [PdCl2(Ph2NNC10H14O)}(2)] is more efficient than [PdCl2 (Me2NNC10H14O)(2)] which is one of the more efficient camphor derived catalysts reported before. In contrast the chelate complexes [Pd(YNC10H14O)(2)] (Y = MeN, PhN) display no catalytic activity. (C)2012 Elsevier B. V. All rights reserved.
• Noyes; Potter, Journal of the American Chemical Society, 1915, vol. 37, p. 201
  作者：Noyes、Potter

  DOI：——

  日期：——
• Forster; Spinner, Journal of the Chemical Society, 1912, vol. 101, p. 1345
  作者：Forster、Spinner

  DOI：——

  日期：——
• Bredt, Chemische Berichte, 1912, vol. 45, p. 1421
  作者：Bredt

  DOI：——

  日期：——