cyclopentanone 4-nitrophenylhydrazone | 3078-07-7

• 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: cyclopentanone 4-nitrophenylhydrazone
• 英文别名: cyclopentanone p-nitrophenylhydrazone；cyclopentanone-(4-nitro-phenylhydrazone)；Cyclopentanon-(4-nitro-phenylhydrazon)；Cyclopentanon-4-nitro-phenylhydrazon；Cyclopentanon-p-nitrophenylhydrazon；N-(cyclopentylideneamino)-4-nitroaniline
• CAS: 3078-07-7
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: QPYVOOSFOUFJIS-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  cyclopentanone 4-nitrophenylhydrazone 在 dimethylammonium chlorochromate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.2h， 生成 环戊酮
  参考文献：
  名称：

  用于从肟、缩氨基脲、4-苯基缩氨基脲和对硝基苯腙中再生羰基化合物的高效、选择性和廉价的负载型氧化剂

  摘要：

  摘要 吸附在硅胶上的氯铬酸二甲基铵 (DMCC/SiO2) 可以在温和和非水条件下以良好的收率从肟、缩氨基脲、4-苯基缩氨基脲和对硝基苯腙中再生羰基化合物。

  DOI：

  10.1080/00397910008087230
• 作为产物：
  描述：

  环戊酮 、 4-硝基苯肼 以 甲苯 为溶剂， 反应 0.17h， 生成 cyclopentanone 4-nitrophenylhydrazone
  参考文献：
  名称：

  3-与α-氧-乙烯酮的1，3-偶极环加成反应：吡唑烷二酮的三组分立体选择性入口和原始的螺氧杂吲哚类

  摘要：

  立体定义的单环，螺双环和双-螺旋三环吡唑并烷-3-酮可通过三组分反应高效制备，该反应涉及从中获得的偶氮甲亚胺与原位生成的α-氧代-乙烯酮双极性亲和剂的1,3-偶极环加成反应。该反应允许在单个催化剂/无添加剂，高度原子经济的转化中以优异的非对映选择性创建四个共价键和两个连续的手性季中心。从基本的观点来看，该反应在1，3-偶极环加成中引入α-氧代-乙烯酮作为有效的偶极亲和性。

  DOI：

  10.1021/ol2016669

文献信息

• Isosteric ramatroban analogs: selective and potent CRTH-2 antagonists
  作者：Michael J. Robarge、David C. Bom、L. Nathan Tumey、Norbert Varga、Elizabeth Gleason、Daniel Silver、Jianping Song、Steven M. Murphy、George Ekema、Chris Doucette、Doug Hanniford、Marc Palmer、Gary Pawlowski、Joel Danzig、Margaret Loftus、Karen Hunady、Bruce A. Sherf、Robert W. Mays、Alain Stricker-Krongrad、Kurt R. Brunden、John J. Harrington、Youssef L. Bennani

  DOI：10.1016/j.bmcl.2004.12.055

  日期：2005.3

  The chemoattractant receptor-homologous molecule expressed on T(H)2 cells (CRTH-2), also found on eosinophils and basophils, is a prostaglandin D-2 receptor involved in the recruitment of these cell types during an inflammatory response. In this report, we describe the synthesis and optimization of a ramatroban isostere that is a selective and potent antagonist of CRTH-2 which may be useful in the treatment of certain diseases. © 2004 Elsevier Ltd. All rights reserved.
• Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Norihiko Takeda、Yasuo Kimura、Yoshiji Takemoto、Norimitsu Tohnai、Mikiji Miyata、Takeaki Naito

  DOI：10.1016/j.tet.2006.01.087

  日期：2006.4

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• The Cleavage of p-Nitrophenylhydrazones and Semicarbazones with Ammonium Chlorochromate Adsorbed on Alumina Under Non-Aqueous Conditions
  作者：Gui-Sheng Zhang、Hui Gong、De-Hong Yang、Mi-Feng Chen

  DOI：10.1080/00397919908086086

  日期：1999.4

  Deprotection of p-nitrophenylhydrazones and semicarbazones to their parent aldehydes and ketones in good yields has been carried out by using ammonium chlorochromate adsorbed on alumina under mild conditions.
• Methylammonium Chlorochromate Adsorbed on Alumina: A Convenient and Efficient Reagent for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition
  作者：Gui-Sheng Zhang、De-Hong Yang、Mi-Feng Chen、Kun Cai

  DOI：10.1080/00397919808005932

  日期：1998.2

  Methylammonium chlorochromate adsorbed on alumina is an easily prepared and stable reagent. With this reagent oximes and p-nitrophenylhydrazones are converted to their corresponding carbonyl compounds in good yields.
• Dimethylammonium Chlorochromate Adsorbed on Alumina:¹A Mild, Convenient and Inexpensive Reagent for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition
  作者：Gui-Sheng Zhang、De-Hong Yang、Mi-Feng Chen

  DOI：10.1080/00397919808004923

  日期：1998.10

  Grimes and p-nitrophenylhydrazones are converted to corresponding carbonyl compounds using dimethylammonium chlorochromate adsorbed on alumina (DMCC/alumina) under non-aqueous condition.