N-(2,6-二氯苯基)苯甲酰胺 | 10286-88-1

• 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-(2,6-二氯苯基)苯甲酰胺
• 英文名称: N-(2,6-dichlorophenyl)benzamide
• 英文别名: N-benzoyl-2,6-dichloroaniline；2',6'-Dichlorobenzanilide；2,6-dichlorobenzanilide；N-phenylbenzamide；benzoic acid-(2,6-dichloro-anilide)；Benzoesaeure-(2,6-dichlor-anilid)
• CAS: 10286-88-1
• 化学式: C₁₃H₉Cl₂NO
• mdl: MFCD00018326
• 分子量: 266.127
• InChiKey: KGDQECZKWWPUTK-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  296.5±30.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2,6-二氯苯基)苯甲酰胺 在 硫酸 作用下， 反应 3.0h， 以68%的产率得到2,6-二氯苯胺
  参考文献：
  名称：

  Ayyangar, N. R.; Kalkote, U. R.; Nikrad, P. V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 9, p. 872 - 877

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯氯甲烷 在 tetrafluoroboric acid 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 生成 N-(2,6-二氯苯基)苯甲酰胺
  参考文献：
  名称：

  Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

  摘要：

  Reactions between nitrite oxides and benzylic carbocations are described. Different results were obtained when the carbocations were generated from the corresponding chlorides with different Lewis acids, with addition products such as benzoxazines, oximes, and amides being produced. Primary, secondary, and tertiary carbocations showed different reactivities. The product ratios strongly depended on the substituents on the aromatic ring of the benzylic carbocations. Evidence for the proposed mechanism is reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200207)2002:14<2411::aid-ejoc2411>3.0.co;2-n

文献信息

• [EN] (THIO)MORPHOLINE DERIVATIVES AS S1P MODULATORS<br/>[FR] DÉRIVÉS DE (THIO)MORPHOLINE MODULATEURS DE S1P
  申请人：ABBOTT HEALTHCARE PRODUCTS BV

  公开号：WO2011023795A1

  公开（公告）日：2011-03-03

  The present invention relates to (thio)morpholine derivatives of the formula (I), wherein R1 is selected from cyano, (2-4C)alkynyl, (1-4C)alkyl, (3-6C)cycloalkyl, (4-6C)cycloalkenyl, (6-8C)bicycloalkyl, (8-10C)bicyclic group, each optionally substituted with (1-4C)alkyl, phenyl, biphenyl, naphthyl, each optionally substituted with one or more substituents independently selected from halogen, (1-4C)alkyloptionally substituted with one or more fluoro atoms, (2-4C)alkynyl, (1-4C)alkoxy optionally substituted with one or more fluoro atoms,amino, di(1-4C)alkylamino, -SO2-(1-4C)alkyl, -CO-(1-4C)alkyl, -CO-O-(1-4C)alkyl, -NH-CO-(1-4C)alkyl and (3-6C)cycloalkyl, phenyl substituted with phenoxy, benzyl, benzyloxy, phenylethyl or monocyclic heterocycle, each optionally substituted with (1-4C)alkyl, monocyclic heterocycle optionally substituted with halogen, (1-4C)alkyl or with phenyl optionally substituted with (1-4C)alkyl, and bicyclic heterocycle optionally substituted with (1-4C)alkyl; A is selected from -CO-O-, -O-CO-, -NH-CO-, -CO-NH, -C=C-, -CCH3-O- and the linking group –Y-(CH2)n-X- wherein Y is attached to R1 and selected from a bond, -O-, -S-, -SO-, -SO2-, -CH2-O-, -CO-, -O-CO-, -CO-O-, -CO-NH-, -NH-CO-, -C=C-and -C≡C-; n is an integer from 1 to 10; and X is attached to the phenylene / pyridyl group and selected from a bond, -O-, -S-, -SO-, -SO2 -, -NH, -CO-, -C=C-and -C≡C-; ring structure B optionally contains one nitrogen atom; R2 is H, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, or halogen; and R3 is (1-4C)alkylene-R5 wherein the alkylene group may be substituted with (CH2)2 to form a cyclopropyl moiety or one or two halogen atoms, or R3 is is (3-6C)cycloalkylene-R5 or -CO-CH2-R5, wherein R5 is -OH, -PO3H2, -OPO3H2, -COOH, -COO(1-4C)alkyl or tetrazol-5-yl; R4 is H or (1-4C)alkyl; R6 is one or more substituents independently selected from H, (1-4C)alkyl or oxo; W is -O-, -S-, -SO- or -SO2-; or a pharmaceutically acceptable salt, a solvate or hydrate thereof; with the proviso that the derivative of formula (I) is not 2-(4-ethylphenyl)-4-morpholinoethanol or 4-[4-(2-hydroxyethyl)-2-morpholinyl]benzeneacetonitrile or a pharmaceutically acceptable salt, a solvate or hydrate thereof. The compounds of the invention have affinity to S1P receptors and may be used in the treatment, alleviation or prevention of S1P receptor mediated diseases and conditions.

  本发明涉及公式（I）的（硫）吗啉衍生物，其中R1从氰基，（2-4C）炔基，（1-4C）烷基，（3-6C）环烷基，（4-6C）环烯基，（6-8C）双环烷基，（8-10C）双环基团中选择，每个基团可选择地取代为（1-4C）烷基，苯基，联苯基，萘基，每个基团可选择地取代为一个或多个取代基，独立选择自卤素，（1-4C）烷基可选择地取代为一个或多个氟原子，（2-4C）炔基，（1-4C）氧烷基可选择地取代为一个或多个氟原子，氨基，二（1-4C）烷基氨基，-SO2-（1-4C）烷基，-CO-（1-4C）烷基，-CO-O-（1-4C）烷基，-NH-CO-（1-4C）烷基和（3-6C）环烷基，苯基取代为苯氧基，苄基，苄氧基，苯乙基或单环杂环烃，每个基团可选择地取代为（1-4C）烷基，单环杂环烃可选择地取代为卤素，（1-4C）烷基或取代为苯基的苯基，可选择地取代为（1-4C）烷基，和双环杂环烃可选择地取代为（1-4C）烷基；A从-CO-O-，-O-CO-，-NH-CO-，-CO-NH，-C=C-，-CCH3-O-和连接基-Y-（CH2）n-X-中选择，其中Y连接到R1并从键，-O-，-S-，-SO-，-SO2-，-CH2-O-，-CO-，-O-CO-，-CO-O-，-CO-NH-，-NH-CO-，-C=C-和-C≡C-中选择；n是1到10的整数；X连接到苯基/吡啶基团并从键，-O-，-S-，-SO-，-SO2-，-NH，-CO-，-C=C-和-C≡C-中选择；环结构B可选择地含有一个氮原子；R2是H，（1-4C）烷基可选择地取代为一个或多个氟原子，（1-4C）氧烷基可选择地取代为一个或多个氟原子，或卤素；R3是（1-4C）烷基-R5，其中烷基基团可取代为（CH2）2形成环丙基基团或一个或两个卤素原子，或R3是（3-6C）环烷基-R5或-CO-CH2-R5，其中R5是-OH，-PO3H2，-OPO3H2，-COOH，-COO（1-4C）烷基或四唑-5-基；R4是H或（1-4C）烷基；R6是一个或多个取代基，独立选择自H，（1-4C）烷基或氧代基；W是-O-，-S-，-SO-或-SO2-；或其药学上可接受的盐，溶剂或水合物；但是，公式（I）的衍生物不是2-（4-乙基苯基）-4-吗啉乙醇或4-[4-（2-羟乙基）-2-吗啉基]苯乙腈或其药学上可接受的盐，溶剂或水合物。本发明的化合物具有对S1P受体的亲和力，可用于治疗、缓解或预防S1P受体介导的疾病和症状。
• [EN] BIPHENYL DERIVATIVE OR ITS SALT, AND PESTICIDE CONTAINING IT AS AN ACTIVE INGREDIENT<br/>[FR] DERIVE DE DIPHENYLE OU SES SELS, ET PESTICIDE DONT IL CONSTITUE LE PRINCIPE ACTIF
  申请人：ISHIHARA SANGYO KAISHA

  公开号：WO2005044007A1

  公开（公告）日：2005-05-19

  A pesticide having stabilized high pesticidal effects for crop plants infected with plant diseases, is presented. The pesticide contains a biphenyl derivative represented by the formula (I) or its salt, as an active ingredient: wherein X, Y and Z are each independently a halogen atom, a hydroxyl group, a formyl group, an alkyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, or the like, A is a carbonyl group, a thiocarbonyl group, an alkylene group, or a single bond, R1 and R2 are each independently a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a formyl group, an alkylcarbonyl group, a cyano group, or the like, and m and n are each independently 0, 1, 2, 3 or 4.

  一种对感染植物病害的作物植物具有稳定高效杀虫效果的杀虫剂被提出。该杀虫剂含有作为活性成分的二苯基衍生物，该衍生物由公式(I)表示或其盐类：其中X、Y和Z各自独立为卤素原子、羟基、甲酰基、可能被取代的烷基、可能被取代的烷氧基、烷硫基、烷基亚磺酰基、烷基亚磺酰基或类似基团，A为羰基、硫羰基、亚烷基或单键，R1和R2各自独立为氢原子、可能被取代的烷基、可能被取代的烯基、可能被取代的炔基、可能被取代的芳基、甲酰基、烷基羰基、氰基或类似基团，而m和n各自独立为0、1、2、3或4。
• On DABAL-Me3 promoted formation of amides
  作者：Nathalie Dubois、Daniel Glynn、Thomas McInally、Barrie Rhodes、Simon Woodward、Derek J. Irvine、Chris Dodds

  DOI：10.1016/j.tet.2013.08.062

  日期：2013.11

  acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic

  的范围和DABAL-ME的效用3个甲基酯和游离羧酸与在各种条件下伯和仲胺（回流，密封管，微波）的联接器相比已经用于显著范围耦合相关的伙伴制备的医药化学中感兴趣的酰胺类化合物。商业微波反应器促进最快的偶联，并允许使用空间位阻显着的胺（伯胺和仲胺）和羧酸衍生物。已显示微波能量对反应系统的影响通常与热效应（过压和过热）有关。
• Microwave-Assisted Organic Synthesis, structure–activity relationship, kinetics and molecular docking studies of non-cytotoxic benzamide derivatives as selective butyrylcholinesterase inhibitors
  作者：Sheeba Wajid、Asma Khatoon、Maria Aqeel Khan、Humaira Zafar、Shama Kanwal、Atta-ur-Rahman、M. Iqbal Choudhary、Fatima Z. Basha

  DOI：10.1016/j.bmc.2019.07.015

  日期：2019.9

  A series of benzamide derivatives 1–12 with various functional groups (–H, –Br, –F, –OCH3, –OC2H5, and –NO2) was synthesized using an economic, and facile Microwave-Assisted Organic Synthesis, and evaluated for acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) activity in vitro. Structure–activity relationship showed that the substitution of –Br group influenced the inhibitory activity against

  一系列的苯甲酰胺衍生物的1 - 12与各种官能团（-H，-Br，-F，-OCH 3，-OC 2 H ^ 5，和-NO 2）用一种经济合成，并且容易微波辅助有机合成，并评估其在体外的乙酰胆碱酯酶（ACHE）和丁酰胆碱酯酶（BCHE）活性。结构-活性关系表明，-Br基团的取代影响了对BCHE酶的抑制活性。发现合成的化合物是BCHE的选择性抑制剂。另外，所有的化合物1 - 12被认为是无细胞毒性的，相比于标准放线菌酮（IC50  = 0.8±0.2 µM）。其中， 与标准加兰他敏氢溴酸盐（IC 50  = 40.83±0.37 µM）相比，化合物3表现出最有效的BCHE抑制活性（IC 50 = 0.8±0.6 µM）。酶动力学研究表明，化合物1，3 - 4，和7 - 8表现为抑制对BCHE的混合模式中，当化合物2，5 - 6和9表现出非竞争性的抑制模式。分子对接研究进一步强调了这些抑制剂与具有催
• Gas Phase Chemistry of Li⁺ with Amides: the Observation of LiOH Loss in Mass Spectrometry
  作者：Cheng Guo、Yuping Zhou、Pengyuan Liu、Yunfeng Chai、Yuanjiang Pan

  DOI：10.1007/s13361-012-0389-8

  日期：2012.7.1

  three sets of compounds that contains an amide bond, including 2-(4, 6-dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide, its derivatives and simpler structures was investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Observed fragment ions include those that reflect loss of LiOH. Other product ions result from the Smiles rearrangement and direct C–S bond cleavage. MS/MS of H/D

  通过电喷雾研究了三组包含酰胺键的化合物的锂+加合物的碰撞诱导解离 (CID) ，包括 2-(4, 6-二甲氧基嘧啶-2-基硫烷基) -N-苯基苯甲酰胺、其衍生物和更简单的结构电离串联质谱 (ESI-MS/MS)。观察到的碎片离子包括那些反映 LiOH 损失的离子。其他产物离子来自 Smiles 重排和直接 C-S 键裂解。H/D 交换产物的 MS/MS 表明发生了从这些化合物的酰胺氮原子到苯环的 1,3-H 转移。选自Li的损失的LiOH +酰胺的加合物通过[M +栗]的CID进一步检查+离子的Ñ -phenylbenzamide和Ñ-苯基肉桂酰胺。LiOH 的损失基本上是前者观察到的唯一裂解反应。对于后者，发现了 LiOH 和 H 2 O 的损失。发现这些化合物的苯环的给电子取代基的存在促进了 LiOH 的消除，而吸电子取代基阻止了这种损失。从超高分辨率傅里叶变换离子回旋共振串联质谱 (FTICR-MS/MS)