吲哚布芬杂质杂质10 | 94814-82-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吲哚布芬杂质杂质10
• 英文名称: 2-(4-nitrophenyl)butanonitrile
• 英文别名: 2-(4-nitrophenyl)butyronitrile；Inakt. α-(4-Nitro-phenyl)-butyronitril；2-(4-nitrophenyl)butanenitrile
• CAS: 94814-82-1
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: FXHXUBNWGNUKGM-UHFFFAOYSA-N

物化性质

• 沸点：
  156-158 °C
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吲哚布芬杂质杂质10 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以95%的产率得到2-(4-硝基苯基)丁酸
  参考文献：
  名称：

  氨基酸直接催化芳基乙腈的级联还原烷基化：布洛芬类似物的高产合成

  摘要：

  已开发出一种新的方法，用于通过亚胺基催化使含芳基乙腈的吸电子基团与醛/酮和1,4-二氢吡啶进行一锅三组分还原烷基化（TCRA）反应。许多TCRA反应产物可直接用于农业和药物化学中。

  DOI：

  10.1016/j.tetlet.2010.07.131
• 作为产物：
  描述：

  2-苯基丁腈 在 硫酸 、 硝酸 作用下， 生成 吲哚布芬杂质杂质10
  参考文献：
  名称：

  Fourneau; Sandulesco, Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 451

  摘要：

  DOI：

文献信息

• Chiral compounds and their resolution synthesis using enantioselective
  申请人：Chiroscience Limited

  公开号：US05661014A1

  公开（公告）日：1997-08-26

  Enantiomeric glutarimides such as aminoglutethimide and rogletimide are prepared by cyclisation of a corresponding ester-nitrile which is a good substrate for biotransformation with an enantiospecific esterase.

  旋光异构体谷氨酰亚胺，如氨戊酰亚胺和罗格利亚胺，是通过相应的酯-腈环化制备的，该酯-腈是一种良好的底物，可通过对映异构酯酶进行对映选择性的生物转化。
• Preparation of nitroaralkyl cyanides and derivatives thereof
  申请人：ETHYL CORPORATION

  公开号：EP0078709A2

  公开（公告）日：1983-05-11

  Nitroarylalkyl cyanides may be prepared in a convenient manner by reacting a nitroaromatic compound with an alpha, alpha-disubstituted alkyl cyanide, e.g. an alpha, alpha-disubstituted acetonitrile, in a substantially anhydrous aprotic solvent and in the presence of a base so that the nitrile undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-subsituent functions as a leaving group. The nitroaralkyl cyanides formed by the process can be readily converted into derivatives, such as pharmaceuticals.

  硝基芳烷基氰化物的制备方法简便易行，硝基芳香族化合物与α、α-二取代烷基氰化物（如α、α-二取代乙腈）在基本无水的无丙烷溶剂中并在碱存在下发生反应，使腈在硝基芳香族化合物的未取代环碳上发生亲核取代反应，其间α-取代基作为离去基团起作用。 通过该工艺形成的硝基芳烷基氰化物可以很容易地转化为衍生物，如药物。
• 一种吲哚布芬关键中间体2-(4-硝基苯基)丁酸的合成方法
  申请人：杭州中美华东制药有限公司

  公开号：CN114516799A

  公开（公告）日：2022-05-20

  本发明公开了一种吲哚布芬关键中间体2‑(4‑硝基苯基)丁酸的合成方法，所述的合成方法包括：在有机溶剂中，在碱性物质的作用下，式Ⅰ所示的化合物与溴乙烷反应得到式Ⅱ所示的化合物，再将式Ⅱ所示的化合物在酸性条件下水解得到式Ⅲ所示的目标产物。本发明所述的方法步骤简单，操作方便，反应无硝化过程，安全性高，污染小，产物的收率高。
• Production of (<i>R</i>)-Aminoglutethimide:  A New Route from 1-Chloro-4-nitrobenzene
  作者：Michael J. Bunegar、Ulrich C. Dyer、Graham R. Evans、Richard P. Hewitt、Stephen W. Jones、Neil Henderson、Christopher J. Richards、Sivadasan Sivaprasad、Benjamin M. Skead、Mark A. Stark、Eric Teale

  DOI：10.1021/op9900075

  日期：1999.11.1

  The development of a short, safe and enantioselective route for the preparation of (R)-aminoglutethimide is described, The process was designed for economic large-scale manufacture of the bulk drug substance to acceptable quality standards, to allow clinical evaluation of the single enantiomer over the existing racemate. (R)-Aminoglutethimide was prepared from 1-chloro-4-nitrobenzene using a six-stage synthetic sequence, via chemoresolution of key intermediate racemic 4-cyano-4-(4-nitrophenyl)hexanoic acid using (-)-cinchonidine, The process allowed for preparation of several kilograms of the precursor (R)-nitroglutethimide, to cGMP at pilot-plant scale, along with demonstration of the find hydrogenation step to (R)-amino-glutethimide in the laboratory, This route avoids the problems of hazardous nitration technology, and therefore regio-isomer contamination of the product, associated with other procedures. The resolution chemistry described represents an improvement on literature procedures, Optimisation of the asymmetric Michael addition offers an attractive alternative approach.
• Resolution of 4-cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (aminoglutethimide1)
  作者：Osman Achmatowicz、Iwona Malinowska、Barbara Szechner、Jan K. Maurin

  DOI：10.1016/s0040-4020(97)00464-x

  日期：1997.6

  Using (R)- or (S)-1-phenylethylamine as a resolving agent, (R)- and (S)-4-cyano-4-(4-nitrophenyl)hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)- and (S)-aminoglutethimide of high (>99% ee) enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3-ethylpiperidine-2, 6-dione was solved by X-ray single crystal analysis thus establishing the (R)-configuration of the dextrorotatory aminoglutethimide. Attempted resolution of the other precursor of aminoglutethimide, 4cyano-2-ethyl(4-nitrophenyl)butanoic acid with (S)-1-phenylethylamine led to the formation of the double salt. Its crystal structure was elucidated by X-ray crystallographic analysis. (C) 1997 Elsevier Science Ltd.