O-methyl 4-phenylcyclohexanone oxime | 476373-78-1

• 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: O-methyl 4-phenylcyclohexanone oxime
• 英文别名: 4-phenylcyclohexanone O-methyloxime
• CAS: 476373-78-1
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: CHHSRHQZZAHCOU-YPKPFQOOSA-N

物化性质

• 沸点：
  307.6±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  O-methyl 4-phenylcyclohexanone oxime 、 溴己烷 在 magnesium 、 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 以0.1046 g的产率得到2-butyl-7-phenyl-1-azaspiro[3.5]nonane
  参考文献：
  名称：

  钛介导的肟肟合成螺环式NH-氮杂环丁烷。

  摘要：

  描述了使用烷基格氏试剂或末端烯烃配体交换偶联伴侣从肟醚的TiIV介导的螺环NH-氮杂环丁烷的合成。通过提出的库林科维奇型机理，钛环丙烷中间体形成并用作1,2-脂族二价阴离子，插入1,2-二亲电子肟醚中，最终产生所需的N-杂环四元环。该转化以中等收率进行，只需一步即可提供先前未报道的且结构多样的NH-氮杂环丁烷。

  DOI：

  10.1002/anie.201909151
• 作为产物：
  描述：

  N-(4-phenylcyclohexylidene)hydroxylamine 、 甲氧基胺盐酸盐 在 吡啶 作用下， 以 乙醇 为溶剂， 以96%的产率得到O-methyl 4-phenylcyclohexanone oxime
  参考文献：
  名称：

  Preparation and Allylation of Enamides and Enecarbamates Generated via Iron(0) Reduction of Oximes and Derivatives

  摘要：

  用铁粉在酸氯化物或氯甲酸酯存在下进行亚胺和亚胺碳酸酯的还原酰化，可生产出烯酰胺或烯碳酸酯。

  DOI：

  10.1055/s-2006-942513

文献信息

• Expanded scope of Griesbaum co-ozonolysis for the preparation of structurally diverse sensors of ferrous iron
  作者：Jun Chen、Ryan L. Gonciarz、Adam R. Renslo

  DOI：10.1039/d1ra05932g

  日期：——

  Improved, low temperature conditions for Griesbaum co-ozonolysis enables the preparation of structurally diverse 1,2,4-trioxolane-based sensors of ferrous iron for caging of reporters and therapeutic payloads.

  改进的低温条件对Griesbaum共臭氧裂解的影响使得能够制备出基于1,2,4-三氧杂环戊烷的结构多样的铁离子传感器，用于封装报告物和治疗载荷。
• Spiro and dispiro 1,2,4-trioxolane antimalarials
  申请人：Medicines for Malaria Venture MMV International Centre Cointrin

  公开号：US06486199B1

  公开（公告）日：2002-11-26

  A means and method for treating malaria using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl or spiropiperidyl ring on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably functionalized or substituted at the 4-position or a spiropiperidyl ring that is functionalized or substituted at the nitrogen atom. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  描述了一种利用螺环或二螺环1,2,4-三噁烷治疗疟疾的方法和手段。首选的1,2,4-三噁烷包括在三噁烷基团的一侧具有螺环戊烷基团，并在三噁烷基团的另一侧具有螺环环己基或螺环哌啶基团，其中螺环环己基环在4-位功能化或取代，或者螺环哌啶基团在氮原子处功能化或取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有强效作用。
• Oxime substituted imidazoquinolines
  申请人：Kshirsagar A. Tushar

  公开号：US20070066639A1

  公开（公告）日：2007-03-22

  Imidazo-containing compounds (e.g., imidazoquinolines, imidazonaphthyridines, and imidazopyridines) with an oxime substituent at the 1-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及含咪唑基的化合物（例如咪唑喹啉，咪唑萘啶和咪唑吡啶），其在1位上具有肟基取代基，包含这些化合物的药物组合物，中间体以及这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• OXIME SUBSTITUTED IMIDAZOQUINOLINES
  申请人：Kshirsagar Tushar A.

  公开号：US20090042925A1

  公开（公告）日：2009-02-12

  Imidazo ring compounds (e.g., imidazoquinolines, 6,7,8,9-tetrahydroimidazoquinolines, imidazonaphthyridines, and imidazopyridines) with an oxime substituent at the 2-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及带有2位置的肟取代基的咪唑环化合物（例如，咪唑喹啉，6,7,8,9-四氢咪唑喹啉，咪唑萘啉和咪唑吡啶），包含这些化合物的制药组合物，中间体以及这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• Spiro and Dispiro-1,2,4-trioxolanes as Antimalarial Peroxides:  Charting a Workable Structure−Activity Relationship Using Simple Prototypes
  作者：Yuxiang Dong、Jacques Chollet、Hugues Matile、Susan A. Charman、Francis C. K. Chiu、William N. Charman、Bernard Scorneaux、Heinrich Urwyler、Josefina Santo Tomas、Christian Scheurer、Christopher Snyder、Arnulf Dorn、Xiaofang Wang、Jean M. Karle、Yuanqing Tang、Sergio Wittlin、Reto Brun、Jonathan L. Vennerstrom

  DOI：10.1021/jm049040u

  日期：2005.7.1

  This paper describes the discovery of synthetic 1,2,4-trioxolane antimalarials and how we established a workable structure-activity relationship in the context of physicochemical, biopharmaceutical, and toxicological profiling. An achiral dispiro-1,2,4-trioxolane (3) in which the trioxolane is flanked by a spiroadamantane and spirocyclohexane was rapidly identified as a lead compound. Nonperoxidic 1,3-dioxolane isosteres of 3 were inactive as were trioxolanes without the spiroadamantane. The trioxolanes were substantially less effective in a standard oral suspension formulation compared to a solubilizing formulation and were more active when administered subcutaneously than orally, both of which suggest substantial biopharmaceutical liabilities. Nonetheless, despite their limited oral bioavailability, the more lipophilic trioxolanes generally had better oral activity than their more polar counterparts. In pharmacokinetic experiments, four trioxolanes had high plasma clearance values, suggesting a potential metabolic instability. The toxicological profiles of two trioxolanes were comparable to that of artesunate.