3-(2-硝基苯基)丙-2-烯-1-胺 | 75059-00-6

• 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: 3-(2-硝基苯基)丙-2-烯-1-胺
• 英文名称: (2-Nitrocinnamyl)amine
• 英文别名: 3-(2-nitrophenyl)prop-2-en-1-amine
• CAS: 75059-00-6
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: GSWGDDFGSAFPKT-UHFFFAOYSA-N

物化性质

• 沸点：
  350.6±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-硝基苯基)丙-2-烯-1-胺 在 氢氧化钾 、 air 、 乙酸酐 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 148.0h， 生成 6,7,12,13-四氢-5H-吲哚并[2,3-a]吡咯并[3,4-c]咔唑-5-酮
  参考文献：
  名称：

  Synthesis of the staurosporine aglycon

  摘要：

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.

  DOI：

  10.1021/jo00033a036
• 作为产物：
  描述：

  2-[3-(2-硝基苯基)丙-2-烯基]异吲哚-1,3-二酮 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 21.5h， 以83%的产率得到3-(2-硝基苯基)丙-2-烯-1-胺
  参考文献：
  名称：

  Synthesis of the staurosporine aglycon

  摘要：

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.

  DOI：

  10.1021/jo00033a036

文献信息

• Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0394058A1

  公开（公告）日：1990-10-24

  Herein disclosed are an α-(aminocydonexyl)alkylamine represented by the following general formula (II): wherein R represents hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, provided that the amino group bonded to the cyclohexyl group may be in either of the 2-, 3- and 4-positions and a method for preparing it; an a-(isocyanatocyclohexyl)alkylisocyanate of Formula (II) wherein the amino groups are replaced with isocyanato groups and a method for preparing it; polyisocyanato-isocyanurate represented by the following general formula (IV): wherein Ri, R2 and R3 may be the same or different and each represents a group represented by the following general formula: wherein R represents hydrogen atom or an alkyl group having 1 to 5 carbon atoms and n is an integer ranging from 1 to 5 and a method for preparing it; and a resin obtained by polymerizing an organic polyisocyanate containing not lower than 10% by weight of the polyisocyanato-isocyanurate represented by Formula (IV) and a compound having at least two active hydrogen atoms as well as a resin composition for coating materials which comprises the resin.

  本发明公开了由以下通式(II)代表的α-(氨基环己基)烷基胺： 其中 R 代表氢原子或具有 1 至 5 个碳原子的低级烷基，但与环己基键合的氨基可位于 2、3 和 4 位中的任一位置；式（II）的 a-(异氰基环己基)烷基异氰酸酯（其中氨基被异氰酸基取代）及其制备方法；由以下通式（IV）表示的聚异氰酸酯： 其中 Ri、R2 和 R3 可以相同或不同，且各自代表下式通式所代表的基团： 其中 R 代表氢原子或具有 1 至 5 个碳原子的烷基，n 为 1 至 5 的整数，以及制备方法；通过聚合有机多异氰酸酯获得的树脂，该有机多异氰酸酯含有不低于 10%（按重量计）的由式(IV)代表的多异氰酸酯和至少具有两个活泼氢原子的化合物，以及包含该树脂的用于涂层材料的树脂组合物。
• BICYCLIC PYRAZOLE COMPOUNDS AS ANTIBACTERIAL AGENTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP1863483A1

  公开（公告）日：2007-12-12
• [EN] BICYCLIC PYRAZOLE COMPOUNDS AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSES DE PYRAZOLE BICYCLIQUES UTILISES COMME AGENTS ANTIBACTERIENS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006105289A1

  公开（公告）日：2006-10-05

  [EN] Antibacterial compounds, compositions containing them, and methods of use for the inhibition of bacterial activity and the treatment, prevention or inhibition of bacterial infection.
  [FR] L'invention concerne des composés antibactériens, des compositions les contenant et leurs procédés d'utilisation pour l'inhibition de l'activité bactérienne et le traitement, la prévention ou l'inhibition de l'infection bactérienne.
• [EN] NOVEL PROCESS FOR PRODUCING BISAMINOPHENYLALKYLUREA<br/>[FR] NOUVEAU PROCÉDÉ DE PRODUCTION DE BISAMINOPHÉNYLALKYLURÉE
  申请人：NISSAN CHEMICAL IND LTD

  公开号：WO2011136231A1

  公开（公告）日：2011-11-03

  　容積効率が高く、副生物が少なく、高純度で、高収率にて目的物であるビスアミノフェニルウレアが製造される。　下式（１）で表わされる（ニトロフェニル）アルキルアミンハロゲン酸塩と、下式（２）で表わされるカルボニル化合物と、をアミド系溶媒中にて塩基の存在下に縮合反応せしめて下式（３）で表わされるニトロ化合物を製造し、　次いで、得られる前記ニトロ化合物を低級アルコール溶媒中にて還元反応せしめることにより式（４）で表わされるビスアミノフェニルアルキルウレアを製造する。
• Synthesis of the staurosporine aglycon
  作者：Christopher J. Moody、Kulsum F. Rahimtoola、Barry Porter、Barry C. Ross

  DOI：10.1021/jo00033a036

  日期：1992.3

  A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the pyranoindolone (35). On heating in bromobenzene, the pyranoindolone 35 undergoes intramolecular Diels-Alder reaction to give, after loss of carbon dioxide and air oxidation, the carbazole 36, which on treatment with triethyl phosphite cyclizes to the staurosporine aglycon. The overall yield from ethyl indole-2-acetate is 22.6%.