N-乙炔基-N-苯基苯胺 | 4231-39-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-乙炔基-N-苯基苯胺
• 英文名称: N-Phenyl-N-ethynyl-aniline
• 英文别名: N-ethynyl-N-phenylaniline；(Diphenylamino)acetylen；N-Ethinyldiphenylamin；ethynyldiphenylamine；Aethinyl-diphenyl-amin；Diphenyl-aethinyl-amin
• CAS: 4231-39-4
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: FIBSTLLRJVXRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2921440000

反应信息

• 作为反应物：
  描述：

  N-乙炔基-N-苯基苯胺 在 盐酸 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 N-[2-Chloro-1-diphenylamino-eth-(Z)-ylidene]-4-nitro-benzenesulfonamide
  参考文献：
  名称：

  Himbert,G.; Regitz,M., Chemische Berichte, 1972, vol. 105, p. 2963 - 2974

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰二苯胺 在 正丁基锂 、 五氯化磷 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成 N-乙炔基-N-苯基苯胺
  参考文献：
  名称：

  Preparations, crystal structures and DFT calculations of novel diacetylenes incorporating ynamine moieties

  摘要：

  Two diacetylene molecules incorporating an ynamine moiety, 5-(diphenylamino)-2,4-pentadiyne-1-ol (1) and 6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol (2), were prepared and characterized by single crystal X-ray diffraction, H-1 and C-13 NMR. The crystal structures of 1 and 2 were solved successfully and were interpreted to be controlled mainly by the intermolecular hydrogen-bondings. The difference in the crystal structures between 1 and 2 was well explained by consideration of the steric repulsion with the methyl groups connected to the carbon atom adjacent to the hydroxyl group in 2. The steric effects of the methyl groups on intra and intercolumnar interaction were found to be important for designing molecular and crystal structures of diacetylene molecules. Although the geometries obtained by DFT calculations showed a good agreement on 2 except for the butadiynyl part, a significant difference was recognized at the environment around the nitrogen of 1. The difference could be explained by the effect of the crystal packing. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.003

文献信息

• [EN] 3-(4-ETHYNYLPHENYL)HEXAHYDROPYRIMIDIN-2,4-DIONE DERIVATIVES AS MODULATORS OF MGLUR4<br/>[FR] DÉRIVÉS 3-(4-ÉTHYNYLPHÉNYL)HEXAHYDROPYRIMIDINE-2,4-DIONE EN TANT QUE MODULATEURS DE MGLUR4
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016146600A1

  公开（公告）日：2016-09-22

  The present invention relates to compounds of formula I wherein Y is C-R1; R1' is hydrogen, F or Cl; R1 is F or Cl; R2 is hydrogen or lower alkyl; R3 is phenyl, pyridinyl or isothiazolyl, wherein the N atom in the pyridinyl group may be in different positions, optionally substituted by one or two halgen atoms; R4 is hydrogen or lower alkyl; Het is a 5-membered heteroaryl group, containg two or three heteroatoms, selected from N, O or S, optionally substituted by lower alkyl, cycloalkyl, lower alkoxyalkyl, heterocycloalkyl, wherein the hetero-atom is O, or lower alkyl substituted by hydroxy, or is a bicyclic heteroaromatic ring, containing two or three N-heteroatoms selected from the groups (II), (III), (IV) or (V) or to a pharmaceutically acceptable salt or acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. The compounds may be used for the treatment of Parkinson's disease, anxiety, emesis, obsessive compulsive disorder, autism, neuroprotection, cancer, depression and diabetes type 2.

  本发明涉及式I的化合物，其中Y为C-R1；R1'为氢、F或Cl；R1为F或Cl；R2为氢或较低的烷基；R3为苯基、吡啶基或异噻唑基，其中吡啶基中的N原子可能在不同位置，可选择地被一个或两个卤素原子取代；R4为氢或较低的烷基；Het为一个含有两个或三个异原子（N、O或S）的5元杂环芳基，可选择地被较低的烷基、环烷基、较低的烷氧基烷基、杂环烷基取代，其中异原子为O，或被羟基取代的较低的烷基，或是一个含有两个或三个N-异原子的双环杂芳环，选择自组（II）、（III）、（IV）或（V）的羟基或是它们的对映体和/或光学异构体和/或立体异构体的药学上可接受的盐或酸加合盐，或者是一个外消旋混合物，或者是其对应的对映体和/或光学异构体和/或立体异构体。这些化合物可用于治疗帕金森病、焦虑、呕吐、强迫症、自闭症、神经保护、癌症、抑郁症和2型糖尿病。
• [EN] ETHYNYL DERIVATIVES<br/>[FR] DÉRIVÉS D'ÉTHYNYLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015128307A1

  公开（公告）日：2015-09-03

  The present invention relates to compounds of formula I, wherein Y is N or C-R1'; R1' is hydrogen or F; R1 is hydrogen, halogen or lower alkyl substituted by halogen; R2 is hydrogen or lower alkyl; or R2 forms together with R4 a 6 membered heterocyclic ring containing -CH2-CH2-O-CH2- or -CH2-CH2-NR-C(O)-; R is hydrogen, lower alkyl, phenyl or benzyl; R3 is phenyl or pyridinyl, wherein the N atom in the pyridinyl group may be in different positions; R4' is hydrogen, lower alkyl or lower alkoxyalkyl; R4 is hydrogen, lower alkyl, phenyl optionally substituted by halogen or lower alkoxy, or is cycloalkyl, or is pyridinyl optionally substituted by halogen, lower alkyl, lower alkoxy or =0, or is pyrimidinyl optionally substituted by lower alkyl, lower alkoxy or =0, or is 1 -lower alkyl-pyridinyl, or is pyrazinyl, or is pyridazinyl optionally substituted by lower alkyl, lower alkoxy or =0, or is l-methylpyrrolo[2,3-b]pyridine-5-yl, or is 6-imidazo[l,2- b]pyridazin-6-yl; or R4 forms together with R4' a 4, 5 or 6 membered heterocyclic ring containing -(CH2)5-, -CH2-CH2-O-CH2-CH2-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-O-CH2-CH2- or CH2-CH2-CH2-O-CH2; R5 and R5' are hydrogen or lower alkyl; or R4 forms together with R5 a saturated 5- membered ring containing -CH2-CH2-CH2-; or to a pharmaceutically acceptable salt or acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. The compounds may be used for the treatment of Parkinson's disease, anxiety, emesis, obsessive compulsive disorder, autism, neuroprotection, cancer, depression and diabetes type 2.

  本发明涉及以下式I的化合物，其中Y为N或C-R1'；R1'为氢或F；R1为氢、卤素或经卤素取代的较低烷基；R2为氢或较低烷基；或R2与R4一起形成一个含有-CH2-CH2-O-CH2-或-CH2-CH2-NR-C(O)-的6元杂环环；R为氢、较低烷基、苯基或苄基；R3为苯基或吡啶基，其中吡啶基中的N原子可能在不同位置；R4'为氢、较低烷基或较低烷氧基烷基；R4为氢、较低烷基、苯基（可选择地经卤素或较低烷氧基取代）、环烷基、或吡啶基（可选择地经卤素、较低烷基、较低烷氧基或=0取代）、或嘧啶基（可选择地经较低烷基、较低烷氧基或=0取代）、或1-较低烷基-吡啶基，或吡嗪基，或吡啶嗪（可选择地经较低烷基、较低烷氧基或=0取代），或1-甲基吡咯并[2,3-b]吡啶-5-基，或6-咪唑并[1,2-b]吡嗪-6-基；或R4与R4'一起形成含有-(CH2)5-、-CH2-CH2-O-CH2-CH2-、-CH2-CH2-CH2-、-CH2-CH2-CH2-CH2-、-CH2-O-CH2-CH2-或CH2-CH2-CH2-O-CH2-的4、5或6元杂环环；R5和R5'为氢或较低烷基；或R4与R5一起形成一个饱和的含有-CH2-CH2-CH2-的5元环；或制药学上可接受的盐或酸加成盐，或消旋混合物，或其相应的对映体和/或光学异构体和/或立体异构体。这些化合物可用于治疗帕金森病、焦虑、恶心、强迫性障碍、自闭症、神经保护、癌症、抑郁症和2型糖尿病。
• Silylcupration of N-phenyl-N-ethynyl-aniline: A versatile route to functionalized N,N-bis(phenyl)enamines
  作者：Laura Capella、Antonella Capperucci、Giovanni Curotto、Dario Lazzari、Pasquale Dembech、Gianna Reginato、Alfredo Ricci

  DOI：10.1016/s0040-4039(00)73691-4

  日期：1993.5

  The silylcupration of N-phenyl-N-ethynyl-aniline, occurs regioselectively leading to silylation at the β-carbon atom. Subsequent reaction of the resulting vinyl copper adduct with electrophiles, opens a new flexible route to functionalized enamines.

  N-苯基-N-乙炔基-苯胺的甲硅烷基化在区域上选择性地发生，导致在β-碳原子处的甲硅烷基化。所得乙烯基铜加合物与亲电子试剂的后续反应为官能化的烯胺开辟了一条新的灵活路线。
• Organic compound having an acetylene group, vacuum deposition polymerization thereof, deposited polymerized thin film, and electroluminescence device containing same
  申请人：——

  公开号：US20020018912A1

  公开（公告）日：2002-02-14

  The present invention relates to an organic compound having acetylene group(s), a thin film formed by vacuum deposition polymerization using said organic compound, vacuum deposition polymerization to form said thin film, and an electroluminescence device containing said thin film. More particularly, the present invention relates to an organic compound having at least one acetylene groups, vacuum deposition polymerization in which said organic compound is deposited on the substrate and simultaneously or then polymerized by heat treatment or UV irradiation to form a polymer thin film, and an electroluminescence device using at least one layer of said thin film.

  本发明涉及一种具有乙炔基的有机化合物，利用该有机化合物进行真空沉积聚合形成的薄膜，利用真空沉积聚合形成该薄膜的方法，以及含有该薄膜的电致发光器件。更具体地，本发明涉及一种至少具有一个乙炔基的有机化合物，在该有机化合物被沉积在基板上并同时或随后通过热处理或紫外线辐射聚合形成聚合物薄膜的真空沉积聚合中，以及使用至少一层该薄膜的电致发光器件。
• Alexakis,A. et al., Bulletin de la Societe Chimique de France, 1977, p. 693 - 698
  作者：Alexakis,A. et al.

  DOI：——

  日期：——