N-(3-甲氧基-4-硝基苯基)乙酰胺 | 20628-19-7

• 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: N-(3-甲氧基-4-硝基苯基)乙酰胺
• 英文名称: 3'-methoxy-4'-nitroacetanilide
• 英文别名: N-(3-Methoxy-4-nitrophenyl)acetamide
• CAS: 20628-19-7
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: ROIFYZDOQOPGNG-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  444.4±35.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(3-甲氧基-4-硝基苯基)乙酰胺 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以90%的产率得到1-氨基-2-甲氧基-4-(N-乙酰氨基)苯
  参考文献：
  名称：

  Azobenzene Photoswitching without Ultraviolet Light

  摘要：

  Most azobenzene-based photoswitches use UV light for photoisomerization. This can limit their application in biological systems, where UV light can trigger unwanted responses, including cellular apoptosis. We have found that substitution of all four ortho positions with methoxy groups in an amidoazobenzene derivative leads to a substantial (similar to 35 rim) red shift of the n-pi* band of the trans isomer, separating it from the cis n-pi* transition. This red shift makes trans-to-cis photoswitching possible using green light (530-560 nm). The cis state is thermally stable with a half-life of similar to 2.4 days in the dark in aqueous solution. Reverse (cis-to-trans) photoswitching can be accomplished with blue light (460 rim), so bidirectional photoswitching between thermally stable isomers is possible without using UV light at all.

  DOI：

  10.1021/ja209239m
• 作为产物：
  描述：

  3’-甲氧基乙酰苯胺 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 以60%的产率得到N-(3-甲氧基-4-硝基苯基)乙酰胺
  参考文献：
  名称：

  用格氏试剂对硝基取代的吲哚，喹啉酮和苯胺进行乙烯基化

  摘要：

  乙烯基格利雅试剂与反应ö -methoxynitroarenes含有电子释放取代基对位通过一个路径，其是从最初的预期Bartoli吲哚合成不同的硝基进行。因此，这些反应并没有给出稠合的吲哚衍生物，而是提供了一种非常温和有效的新方法，用于合成含有邻硝基乙烯基部分的合成相关芳族体系，例如5-硝基-4-乙烯基吲哚，6-硝基-7-硝基。乙烯基吲哚，6-硝基-5-乙烯基-2-（1 H）喹啉酮和4-硝基-3-乙烯基苯胺。

  DOI：

  10.1002/chem.200901322

文献信息

• PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
  申请人：Arora Nidhi

  公开号：US20120015962A1

  公开（公告）日：2012-01-19

  Compounds of the formula I or II: wherein X, m, Ar, R 1 and R 2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

  式I或II的化合物： 其中X，m，Ar，R1和R2如本文所定义。所述化合物对于治疗IRAK介导的疾病是有用的。
• Vinylation of Nitro-Substituted Indoles, Quinolinones, and Anilides with Grignard Reagents
  作者：Riccardo Egris、Mercedes Villacampa、J. Carlos Menéndez

  DOI：10.1002/chem.200901322

  日期：2009.10.19

  that is different from the initially expected Bartoli indole synthesis. Thus, instead of giving fused indole derivatives, these reactions provide a very mild and efficient new procedure for the synthesis of synthetically relevant aromatic systems containing an o‐nitrovinyl moiety, such as 5‐nitro‐4‐vinylindoles, 6‐nitro‐7‐vinylindoles, 6‐nitro‐5‐vinyl‐2(1H)quinolinones, and 4‐nitro‐3‐vinylanilines.

  乙烯基格利雅试剂与反应ö -methoxynitroarenes含有电子释放取代基对位通过一个路径，其是从最初的预期Bartoli吲哚合成不同的硝基进行。因此，这些反应并没有给出稠合的吲哚衍生物，而是提供了一种非常温和有效的新方法，用于合成含有邻硝基乙烯基部分的合成相关芳族体系，例如5-硝基-4-乙烯基吲哚，6-硝基-7-硝基。乙烯基吲哚，6-硝基-5-乙烯基-2-（1 H）喹啉酮和4-硝基-3-乙烯基苯胺。
• Syntheses and photophysical properties of fluorescent dibenzofurans, a dibenzothiophene, and carbazoles substituted with benzoxazole and hydroxyl groups to produce excited state intramolecular proton-transfer
  作者：Joel M. Kauffman、Peter T. Litak、Walter J. Boyko

  DOI：10.1002/jhet.5570320523

  日期：1995.9

  Dibenzofurans, a dibenzothiophene, and carbazoles, each substituted with a 2-benzoxazolyl group as well as an ortho-hydroxyl group, were synthesized to produce fluors with fluorescence due to excited-state intramolecular proton-transfer. The orientations for Friedel-Crafts acylation of 3-methoxydibenzothio-phene and of the analogous carbazole were determined. The fluors displayed absorption peaks in

  合成了各自被2-苯并恶唑基以及邻羟基取代的二苯并呋喃，二苯并噻吩和咔唑，以由于激发态分子内质子转移而产生具有荧光的荧光。确定了3-甲氧基二苯并噻吩和类似咔唑的Friedel-Crafts酰化的取向。荧光显示出在330-385 nm区域的吸收峰，摩尔消光系数高达57,000。在波长为540-600 nm的波长处获得的荧光量子效率为0.17-0.44。氟有可能在闪烁聚苯乙烯纤维中用作波长转换剂。
• Cardiotonic agents. 1. Synthesis and structure-activity relationships in a new class of 3-, 4- and 5-pyridyl-2(1H)-quinolone derivatives
  作者：Gerard Leclerc、Gilbert Marciniak、Nicole Decker、Jean Schwartz

  DOI：10.1021/jm00162a002

  日期：1986.12

  A series of 3-, 4-, and 5-pyridyl-2(1H)-quinolone derivatives with H or HO or CH3O substituents in the 8-position were prepared and tested for positive inotropic activity. Several derivatives, especially 29, 9b, and 27 with a pyridyl ring in the 5-position, were ca. 2-10 times more potent on left guinea pig atria than sulmazole (ARL-115) and milrinone used as references. Some structure-activity relationships

  制备了一系列在8位具有H或HO或CH3O取代基的3-，4-和5-吡啶基-2（1H）-喹诺酮衍生物，并测试了其正性肌力活性。大约有几个衍生物，特别是在5位带有吡啶环的29、9b和27。左豚鼠心房的效力是舒马唑（ARL-115）和米力农用作参考的2-10倍。讨论了一些构效关系。
• Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
  申请人：American Home Products Corporation

  公开号：US20010039348A1

  公开（公告）日：2001-11-08

  Compounds having the formula: 1 wherein R 1 -R 5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, —CN, —NO 2 , —CO 2 R 6 , —COR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , —CONR 7 R 8 , —NR 6 N(R 7 R 8 ), —N(R 7 R 8 ) or W-Y-(CH 2 ) n -Z provided that at least one of R 1 -R 5 is not hydrogen; or R 1 and R 2 or R 3 and R 4 , taken together form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R 6 and R 7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R 8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R 7 and R 8 , taken together may form a 3 to 7 membered heterocycloalkyl; W is O, NR 6 , or is absent; Y is —(CO)— or —(CO 2 )—, or is absent; Z is alkyl of 1 to 4 carbon atoms, —CN, —CO 2 R 6 , COR 6 , —CONR 7 R 8 , —OCOR 6 , —NR 6 COR 7 , —OCONR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , SR6N(R7R8), —N(R 7 R 8 ) or phenyl; G is aryl or fused bicyclic heteroaryl; X is a bond, —NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6; useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  化合物的化学式为1，其中R1-R5独立选择自氢、1到6个碳原子的烷基、2到6个碳原子的烯基、2到6个碳原子的炔基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个碳成员的杂环烷基、芳基、杂芳基、卤素、-CN、-NO2、-CO2R6、-COR6、-OR6、-SR6、-SOR6、-SO2R6、-CONR7R8、-NR6N（R7R8）、-N（R7R8）或W-Y-（CH2）n-Z，其中至少一个R1-R5不是氢；或R1和R2或R3和R4，一起形成3到7个成员的杂环烷基或3到7个成员的杂芳基；R6和R7独立地为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基或芳基；R8为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个成员的杂环烷基、芳基或杂芳基，或R7和R8一起形成3到7个成员的杂环烷基；W为O、NR6或不存在；Y为-CO-或-CO2-，或不存在；Z为1到4个碳原子的烷基、-CN、-CO2R6、COR6、-CONR7R8、-OCOR6、-NR6COR7、-OCONR6、-OR6、-SR6、-SOR6、-SO2R6、SR6N（R7R8）、-N（R7R8）或苯基；G为芳基或融合的双环杂芳基；X为键、-NH、1到6个碳原子的烷基、1到6个碳原子的烯基、1到6个碳原子的烷氧基、1到6个碳原子的硫代烷基、1到6个碳原子的烷基氨基或（CH）J；J为1到6个碳原子的烷基、3到7个碳原子的环烷基、苯基或苄基；n为1到6的整数。该化合物可用于治疗与疱疹病毒相关的疾病，包括人类巨细胞病毒、单纯疱疹病毒、EB病毒、水痘-带状疱疹病毒、人类疱疹病毒-6和-7以及卡波西疱疹病毒。