camphorquinone-3-oxime | 663-17-2

• 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: camphorquinone-3-oxime
• 英文别名: 1,7,7-trimethyl-3-(HON-imino)bicyclo[2.2.1]heptan-2-one；camphorquinone monoxime；camphorquinone monooxime；3-Hydroxyiminocamphor；3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 663-17-2
• 化学式: C₁₀H₁₅NO₂
• mdl: MFCD01101072
• 分子量: 181.235
• InChiKey: YRNPDSREMSMKIY-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R22,R43

反应信息

• 作为反应物：
  描述：

  camphorquinone-3-oxime 在 盐酸 、 聚合甲醛 作用下， 以98%的产率得到樟脑醌
  参考文献：
  名称：

  An Improved Synthesis of Camphorquinone-3-Oxime

  摘要：

  Camphorquinone 3-oxime is prepared in 77% yield in one step from camphor. The synthesis avoids the use of toxic selenium reagents, and provides the syn compound as the major stereoisomer.

  DOI：

  10.1080/00397919908086451
• 作为产物：
  描述：

  樟脑 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 camphorquinone-3-oxime
  参考文献：
  名称：

  由新颖樟脑催化醛的对映选择性硅氰化反应衍生的席夫碱 - 钛（IV）配合物

  摘要：

  五三齿席夫碱已经从（1制备- [R，2小号，3 - [R，4小号）-3-氨基- 1,7,7-三甲基二环[2.2.1]庚-2-醇和水杨醛。X射线结构的调查显示在它们的分子构象的差异，和它们的钛（IV）络合物进行了研究NMR技术。它们之间的复合物与由2-羟基-3-异丙基苯甲醛得到的席夫碱，为脂肪族，脂环族，芳族，杂芳族和醛的硅氰化反应最有选择性的催化剂。最高的对映选择性，> 99％时，在加入三甲基氰硅烷的给肉桂醛实现。

  DOI：

  10.1016/j.tetasy.2014.03.001

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。
• Nitro–ruthenium(<scp>ii</scp>)–arylazoimidazoles: synthesis, spectra, crystal structure and electrochemistry of dinitro-bis{1-alkyl-2-(arylazo)imidazole}ruthenium(<scp>ii</scp>). Nitro–nitroso derivatives and reactivity of the electrophilic {Ru-NO}⁶system
  作者：P. Byabartta、Sk. Jasimuddin、B. K. Ghosh、C. Sinha、A. M. Z. Slawin、J. D. Woollins

  DOI：10.1039/b204442k

  日期：——

  (E1/2M) of 10b–12b are anodically shifted by ∼0.2 V as compared to those of dinitro precursors 7b–9b. The ν(NO)>1900 cm−1 strongly suggests the presence of linear Ru–N–O bonding. The electrophilic behaviour of metal bound nitrosyl has been proved in one case (12b) by reacting with a bicyclic ketone, camphor, containing an active methylene group and an arylhydrazone with an active methine group, and the heteroleptic

  银离子辅助水合蓝色顺式，反式，顺式-RuCl 2（RaaiR'）2 （4 – 6）导致溶剂化物种，蓝色-紫色顺式，反式，顺式-[Ru（OH 2）2（RaaiR'）2 ]（ ClO 4）2 [RaaiR' = p -R–C 6 H 4 –N N–C 3 H 2 –NN-1-R'（1 – 3），缩写为N，N'-螯合剂，其中N（咪唑）和N（偶氮）分别代表N和N'；[R = H（一）中，Me（b），CL（C ^）和R' =我（1 / 4 / 7 / 10），CH 2 CH 3（2 / 5 / 8 / 11），CH 2 Ph（上3 / 6 / 9 / 12）]已反应与NO 2 -在温暖乙醇得到的紫色二硝基配合物类型为Ru（NO 2）2（RaaiR'）2 （7 – 9）。在一种情况下，[Ru（NO 2）2（HaaiCH 2 Ph）2 ]（9a）的结构已通过X射线衍射确定为顺式-Ru（NO 2）2基序和
• Method For Enantioselective Preparation Of Sulphoxide Derivatives
  申请人：Cohen Avraham

  公开号：US20070299261A1

  公开（公告）日：2007-12-27

  The present invention concerns enantioselective preparation of sulphoxide derivatives or their salts. The method consist in performing an enantioselective oxidation of a sulphur of general formula (I) A-CH 2 —SB, wherein: A is a diversely substituted pyridinyl ring and B is a heterocyclic radical comprising an imidazo-pyridinyl ring, using an oxidizing agent in the presence of a titanium (IV) -based catalyst and a chiral ligand consisting of a cyclic beta or gamma-amino-alcohol, in an organic solvent, followed, if required, by salt formation with a base. The invention is useful for preparing sulphoxides useful in therapeutics.

  本发明涉及对亚砜衍生物或其盐的对映选择性制备。该方法包括在一般式（I）A-CH2-SB的硫上进行对映选择性氧化，其中：A是多样取代的吡啶环，B是含有咪唑吡啶环的杂环基，使用一种氧化剂，在钛（IV）基催化剂和由环状β或γ-氨基醇组成的手性配体的存在下，在有机溶剂中进行，随后，如有必要，通过碱形成盐。该发明对于制备在治疗中有用的亚砜具有用处。
• Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa
  作者：Joana P. Costa、Sílvia A. Sousa、Catarina Soeiro、Jorge H. Leitão、Adelino M. Galvão、Fernanda Marques、M. Fernanda N. N. Carvalho

  DOI：10.3390/antibiotics10101272

  日期：——

  Fourteen new camphorimine Au(I) complexes were synthesized and characterized by spectroscopic (NMR, FTIR) and elemental analysis. The structural arrangement of three selected examples were computed by Density Functional Theory (DFT) showing that the complexes essentially keep the AuI-CN} unit. The Minimum Inhibition Concentrations (MIC) were assessed for all complexes showing that they are active towards the Gram-negative strains E. coli ATCC25922, P. aeruginosa 477, and B. contaminans IST408 and the Gram-positive strain S. aureus Newman. The complexes display very high activity towards P. aeruginosa 477 and B. contaminans IST408 with selectivity towards B. contaminans. An inverse correlation between the MIC values and the gold content was found for B. contaminans and P. aeruginosa. However, plots of MIC values and Au content for P. aeruginosa 477 and B. contaminans IST408 follow distinct trends. No clear relationship could be established between the MIC values and the redox potentials of the complexes measured by cyclic voltammetry. The MIC values are essentially independent of the redox potentials either cathodic or anodic. The complexes K3[Au(CN)2}3(A4L)] (8, Y = m-OHC6H4) and K3[Au(CN)2}3(B2L)]·3H2O (14, Z = p-C6H4) display the lower MIC values for the two strains. In normal fibroblast cells, the IC50 values for the complexes are ca. one order of magnitude lower than their MIC values, although higher than that of the precursor KAu(CN)2.

  合成了14个新的松香胺Au(I)配合物，并通过光谱学（NMR，FTIR）和元素分析进行了表征。通过密度泛函理论（DFT）计算，选取了三个样品的结构排列，显示配合物基本保持AuI-CN}单元。评估了所有配合物的最小抑菌浓度（MIC），显示它们对革兰氏阴性菌E. coli ATCC25922、P. aeruginosa 477和B. contaminans IST408以及革兰氏阳性菌S. aureus Newman都具有活性。配合物对P. aeruginosa 477和B. contaminans IST408表现出非常高的活性，对B. contaminans具有选择性。对于B. contaminans和P. aeruginosa，MIC值与金含量呈反相关。然而，对于P. aeruginosa 477和B. contaminans IST408的MIC值和金含量的图表遵循不同的趋势。通过循环伏安法测量的配合物的氧化还原电位与MIC值之间没有明显的关系。MIC值无论是阴极还是阳极电位都基本独立。配合物K3[Au(CN)2}3(A4L)]（8，Y = m-OHC6H4）和K3[Au(CN)2}3(B2L)]·3H2O（14，Z = p-C6H4）对两种菌株的MIC值较低。在正常成纤维细胞中，配合物的IC50值约比它们的MIC值低一个数量级，但高于前体KAu(CN)2的IC50值。
• 3-amino-2-hydroxybornane derivatives, asymmetric Michael reaction using
  申请人：Nippon Mining Co., Ltd.

  公开号：US05146003A1

  公开（公告）日：1992-09-08

  A 3-amino-2-hydroxybornane derivative represented by formula (I): ##STR1## wherein R represents a furfuryl group, a 1-methylpyrrolylmethyl group, or a benzyl group, is disclosed. The compound is useful as a ligand in an asymmetric Michael reaction, particularly for the production of an optically active muscone.

  本发明公开了一种由式（I）表示的3-氨基-2-羟基伯纳烷衍生物：##STR1## 其中R代表呋喃基、1-甲基吡咯甲基或苄基。该化合物可用作不对称Michael反应中的配体，特别是用于生产光学活性麝香酮。