2-甲基-3-硝基苯甲酰氯 | 39053-41-3

• 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: 2-甲基-3-硝基苯甲酰氯
• 英文名称: 2-methyl-3-nitrobenzoyl chloride
• 英文别名: 3-nitro-2-methylbenzoic acid chloride；2-methyl-3-nitrobenzoic acid chloride
• CAS: 39053-41-3
• 化学式: C₈H₆ClNO₃
• 分子量: 199.594
• InChiKey: UENLNPJRTOHQIC-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  286.7±20.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  2-甲基-3-硝基苯甲酰氯 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2-甲基-3-硝基苄氯
  参考文献：
  名称：

  Synthesis of 4-N,N-dialkylaminoethyl-2-indolones as potential dopamine agonists

  摘要：

  A set of fourteen 4-(2-[N-propyl-N-alkyl-(or alkylaryl-) amino]ethyl)-2-indolone analogues of dopamine were synthesized in 15 steps and evaluated for their affinities towards the D-2 receptor using [H-3]sulpiride or [H-3]spiperone as radioligands. Six analogues displayed D-2 agonist activities comparable (K-i = 450650 nM) to Ropinirole or SK&F 101468. The functionalized amino side chain introduced in the 4-position can be used to modulate the lipophilicity of the analogues without significantly affecting D-2 activity.

  DOI：

  10.1016/0223-5234(96)88317-6
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸 在 吡啶 、 氯化亚砜 作用下， 反应 3.0h， 生成 2-甲基-3-硝基苯甲酰氯
  参考文献：
  名称：

  新型取代的 5-苯胺基-α-呋喃葡萄糖衍生物的合成及抗增殖活性

  摘要：

  为了寻找高效低毒的新型抗肿瘤候选药物，设计、合成了 14 种新型取代的 5-苯胺基-α-呋喃葡萄糖衍生物并评估了其体外抗增殖活性。它们的结构通过 NMR（1H 和 13C）和 HR-MS 表征，C（5）的构型（R/S）通过二维 1H,1H-NOESY-NMR 谱进行鉴定。通过MTT测定研究了它们对人肿瘤细胞的抗增殖活性。结果表明，大多数合成的化合物具有与参考药物吉非替尼和拉帕替尼相当的抗增殖作用。特别是，(5R)-5-O-(3-chloro-4-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}anilino)-5-deoxy-1,2-O-(1 -甲基亚乙基)-α-呋喃葡萄糖 (9da) 对 SW480 显示出最有效的抗增殖作用，A431 和 A549 细胞，IC50 值分别为 8.57、5.15 和 15.24 μm。这项工作提出了 5-苯胺基-α-呋喃葡

  DOI：

  10.1002/cbdv.201900739

文献信息

• Synthesis of styrene and stilbene derivatives by the palladium-catalysed arylation of ethylene with aroyl chlorides
  作者：Alwyn Spencer

  DOI：10.1016/s0022-328x(00)98836-3

  日期：1983.5

  with aroyl chlorides, catalysed by palladium(II) acetate, leads to styrene and stilbene derivatives. By appropriate choice of reaction conditions, particularly the ethylene pressure, the reaction can be made to produce either styrene or stilbene derivatives selectively. The reaction tolerates those common substituents which do not react with aroyl chlorides. Only trans-stilbene derivatives are formed

  在乙酸钯（II）的催化下，乙烯与芳酰氯发生芳基化反应，生成苯乙烯和二苯乙烯衍生物。通过反应条件，特别是将乙烯压力适当选择，反应可以进行，以选择性地产生任一苯乙烯或茋衍生物。该反应容许不与芳酰氯反应的那些常见的取代基。仅形成反式-二苯乙烯衍生物。
• [EN] TETRAZOLINONE COMPOUNDS AND ITS USE AS PESTICIDES<br/>[FR] COMPOSÉS DE TÉTRAZOLINONE ET LEUR UTILISATION EN TANT QUE PESTICIDES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2013162072A1

  公开（公告）日：2013-10-31

  The present invention provides a compound having an excellent efficacy for controlling pests. A tetrazolinone compound of a formula (1): [wherein R1 represents an C6-C16 aryl group, an C1-C12 alkyl group, or a C3-C12 cycloalkyl group, etc., which each optionally be substituted; R2, R3, R4 and R5 represent independently of each other a hydrogen atom, a halogen atom or an C1-C3 alkyl group, etc.; R6 represents an C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, an C2-C6 alkenyl group, an C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, etc.; R7, R8 and R9 represent independently of each other a hydrogen atom, a halogen atom, or an C1-C4 alkyl group, etc.; X represents an oxygen atom or a sulfur atom; and R10 represents an C1-C6 alkyl group, etc.] shows an excellent controlling efficacy on pests.

  本发明提供了一种具有优异杀虫效果的化合物。公式（1）的四唑酮化合物：[其中R1代表C6-C16芳基、C1-C12烷基或C3-C12环烷基等，每个都可以选择性地被取代；R2、R3、R4和R5分别独立地代表氢原子、卤素原子或C1-C3烷基等；R6代表C1-C6烷基、C3-C6环烷基、卤素原子、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基或C1-C6卤代烷氧基等；R7、R8和R9分别独立地代表氢原子、卤素原子或C1-C4烷基等；X代表氧原子或硫原子；R10代表C1-C6烷基等]在杀虫方面表现出优异的控制效果。
• Improved synthesis of sterically encumbered heteroaromatic biaryls from aromatic β-keto esters
  作者：Brandon R. Rosen、Ehesan Ul Sharif、Dillon H. Miles、Nicholas S. Chan、Manmohan R. Leleti、Jay P. Powers

  DOI：10.1016/j.tetlet.2020.151855

  日期：2020.5

  A protocol for the synthesis of hindered 4-aryl 2-aminopyrimidines from β–keto esters is described. The process employs trifluoroethanol as an essential additive to promote the guanidine condensation reaction, enabling the synthesis of 25 aryl- and heteroaryl substituted aminopyrimidines in good yields and high purities with no column chromatography. The conditions described herein are readily scalable

  描述了由β-酮酸酯合成受阻4-芳基2-氨基嘧啶的方法。该方法采用三氟乙醇作为促进胍缩合反应的必要添加剂，无需柱色谱法即可以高收率和高纯度合成25个芳基和杂芳基取代的氨基嘧啶。本文所述的条件易于扩展，并且已用于临床A 2a / A 2b R拮抗剂AB928的大规模合成。
• The palladium-catalysed arylation of activated alkenes with aroyl chlorides
  作者：Hans-Ulrich Blaser、Alwyn Spencer

  DOI：10.1016/s0022-328x(00)82707-2

  日期：1982.7

  Aroyl chlorides react with activated alkenes in presence of a tertiary amine and a catalytic amount of palladium acetate to give arylated alkenes, specifically cinnamic acid derivatives and stilbenes. The reaction involves a highly efficient decarbonylation of the aroyl chloride. High yields can be obtained at low catalyst concentration by choice of an appropriate base. The reaction is not particularly

  芳酰氯在叔胺和催化量的乙酸钯的存在下与活化的烯烃反应，得到芳基化的烯烃，特别是肉桂酸衍生物和丁苯甲酸酯。该反应涉及芳酰氯的高效脱羰。通过选择合适的碱，可以在低催化剂浓度下获得高收率。尽管对强电子给体基团是有利的（产率高达98％），但是该反应对芳酰氯中的取代基不是特别敏感。用单取代的烯烃几乎完全特异性地形成E-异构体。提出了反应机理。
• Synthesis of 2-Arylbenzothiazoles by DDQ-Promoted Cyclization of Thioformanilides; A Solution-Phase Strategy for Library Synthesis
  作者：D. Bose、Mohd. Idrees、Bingi Srikanth

  DOI：10.1055/s-2007-965929

  日期：2007.3

  Several substituted benzothiazoles were synthesized by the intramolecular cyclization of thioformanilides using 2,6-dichloro-3,5-dicyano-1,4-benzoquinone (DDQ) in dichloromethane at ambient temperature in high yields. The resulting 2-arylbenzothi­azoles were separated from the reduced DDQ byproduct 4,5-dichloro-3,6-dihydroxyphthalonitrile by treatment of the reaction mixture with a strongly basic ion-exchange resin. This protocol offers a high degree of flexibility with regard to the functional groups that can be placed on the benzothiazole ring or 2-aryl moiety, which in turn generates scaffolds for parallel synthesis.

  数种取代苯并噻唑通过分子内环化，在高产率下合成，以硫代酰胺与2,6-二氯-3,5-二氰基-1,4-苯醌（DDQ）在二氯甲烷中室温反应。所得到的2-芳基苯并噻唑可通过用强碱性离子交换树脂处理反应混合物，从还原型DDQ副产物（4,5-二氯-3,6-二羟基邻苯二腈）中分离出来。本方法在苯并噻唑环或2-芳基部分上引入官能团具有高度的灵活性，进而为平行合成提供了骨架。