3-甲基苯并呋喃-2-甲酸甲酯 | 2076-36-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-甲基苯并呋喃-2-甲酸甲酯
• 中文别名: 3-苯并呋喃-2-羧酸乙酯
• 英文名称: methyl 3-methylbenzofuran-2-carboxylate
• 英文别名: methyl 3-methyl-2-benzofurancarboxylate；methyl 3-methylbenzofuran-2-carboxylate；3-methyl-benzofuran-2-carboxylic acid methyl ester；3-Methyl-benzofuran-2-carbonsaeure-methylester；3-methylbenzofuran-2-carboxylic acid methyl ester；methyl 3-methyl-benzofuran-2-carboxylate；methyl 3-methyl-1-benzofuran-2-carboxylate
• CAS: 2076-36-0
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD09270117
• 分子量: 190.199
• InChiKey: HVUOTQOUAMXGLR-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  130-135 °C(Press: 1 Torr)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-甲基苯并呋喃-2-甲酸甲酯 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 1.0h， 生成 3-甲基-苯并呋喃-2-甲醛
  参考文献：
  名称：

  合成和评估2-吡啶酮衍生物作为HIV-1特异性逆转录酶抑制剂。2.3-氨基吡啶-2（1H）-1的类似物。

  摘要：

  合成了一系列非核苷3-氨基吡啶-2（1H）-一衍生物，并评估了其对HIV-1 RT的抑制作用。在使用rC.dG作为模板引物的酶分析中，几种类似物被证明是有效的高选择性拮抗剂，体外IC50值低至19 nM。该系列中的两种化合物，3-[[[（4,7-二甲基苯并恶唑-2-基）甲基]-氨基] -5-乙基-6-甲基吡啶2-2（1H）-一个（34，L-697,639）和相应的4,7-二氯类似物（37，L-697,661）在浓度为25-50 nM的MT4细胞培养物中可抑制HIV-1 IIIb感染的传播达95％，并被选作临床试验的抗病毒药。

  DOI：

  10.1021/jm00099a007
• 作为产物：
  描述：

  N-phenoxyphthalimide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 sodium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 3-甲基苯并呋喃-2-甲酸甲酯
  参考文献：
  名称：

  铑（III）催化的N-苯氧基乙酰胺和炔烃的氧化还原-中性偶联，具有可调的选择性

  摘要：

  给它一个调整：一种新颖的氧化定向基团被用于铑（III）催化的开发Ç  h的官能Ñ与炔-phenoxyacetamides。反应条件的微小变化会导致邻-羟苯基取代的酰胺或环化反应以高选择性提供苯并呋喃（参见方案； Cp * = C 5 Me 5）。

  DOI：

  10.1002/anie.201300881

文献信息

• Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation
  作者：Haiwen Xiao、Zhonglin Liu、Haigen Shen、Benxiang Zhang、Lin Zhu、Chaozhong Li

  DOI：10.1016/j.chempr.2019.02.006

  日期：2019.4

  Direct trifluoromethylation of C(sp3)–H bonds, especially in late stages, remains a formidable challenge. Herein, we describe the copper-catalyzed benzylic C(sp3)–H trifluoromethylation. With Cu(I) or Cu(II) as the catalyst, (bpy)Zn(CF3)2 (bpy = 2,2′-bipyridine) as the CF3 source, and NFSI (or Selectfluor) as the oxidant, site-selective benzylic C(sp3)–H trifluoromethylation is successfully implemented

  C（sp 3）–H键的直接三氟甲基化，尤其是在后期阶段，仍然是一个艰巨的挑战。在这里，我们描述了铜催化的苄基C（sp 3）–H三氟甲基化。以Cu（I）或Cu（II）为催化剂，以（bpy）Zn（CF 3）2（bpy = 2,2'-联吡啶）作为CF 3源，以NFSI（或Selectfluor）作为氧化剂选择性苄基C（sp 3）–H三氟甲基化已在温和条件下成功高效地实施。该协议不仅展示了广泛的底物范围和广泛的官能团兼容性，而且还允许对天然产物或药物衍生物进行有效的后期C（sp 3）–H三氟甲基化。
• [EN] ACETYLENE DERIVATIVES AS INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] DERIVES D'ACETYLENE EN TANT QU'INHIBITEURS D'HISTONE DEACETYLASE
  申请人：AXYS PHARM INC

  公开号：WO2005019174A1

  公开（公告）日：2005-03-03

  The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.

  本发明涉及某些羟肟酸酯衍生物，它们是组蛋白去乙酰化酶的抑制剂，因此在治疗与组蛋白去乙酰化酶活性相关的疾病方面具有用处。还公开了制备这些化合物的药物组合物和方法。
• Benzofuran Derivatives. I. On the Effects of Substituents in Benzofuran Syntheses
  作者：Tsuneo Suzuki、Takaaki Horaguchi、Takahachi Shimizu、Teishiro Abe

  DOI：10.1246/bcsj.56.2762

  日期：1983.9

  of 4-substituted 2-acylphenoxyacetic acids give a mixture of benzofurans and 2-benzofurancarboxylic acids. The relative yields of benzofurans and 2-benzofurancarboxylic acids depend on the substituents on the benzene ring of the 2-acylphenoxyacetic acids. Electron-withdrawing substituents such as nitro groups favor the formation of 2-benzofurancarboxylic acids. On the other hand, the formation of benzofurans

  4-取代的2-酰基苯氧基乙酸的Rossing反应得到苯并呋喃和2-苯并呋喃甲酸的混合物。苯并呋喃和 2-苯并呋喃甲酸的相对产率取决于 2-酰基苯氧乙酸苯环上的取代基。吸电子取代基如硝基有利于形成 2-苯并呋喃甲酸。另一方面，在 2-酰基-4-硝基苯氧乙酸与无水乙酸钠和乙酸酐的反应中，2-酰基的空间位阻有利于苯并呋喃的形成。
• Acetals containing a cyanoacetyl group
  申请人：DU PONT

  公开号：US02680732A1

  公开（公告）日：1954-06-08

  The invention comprises polymeric acetals of aldehydes of the formula OHC-R-CO-CH2CN where R is a divalent heterocyclic or carbocyclic aromatic radical attached to the -CO and OHC-groupings by carbon atoms forming part of the ring system, with a polymeric polyhydric alcohol, such as polyvinyl alcohol. Preferably the polyvinyl alcohol chain contains at least 25 hydroxyl groups per 100 carbon atoms in the chain, between 0.75 per cent. and 10 per cent. of which are acetalized by an aldehyde according to the above general formula and 0.1 per cent. to 5 per cent. are acetalized with an aldehyde containing a sulphonic or carboxylic acid group, e.g. o-sulphobenzaldehyde. Preferably R is a hydrocarbon nucleus such as benzene, or a heterocyclic nucleus containing at least one oxygen, sulphur or nitrogen hetero atom. The acetals are prepared by reacting a monomeric acetal of a cyanoacetylaryl aldehyde (see Group IV (b)), suitably one of the formula where A is the residue of a 1:2 or 1:3 diol, with a hydroxyl polymer containing a large number of recurring -CH2-CHOH-groups. In examples there are prepared the polyvinyl alcohol acetals of (1) 5-cyanoacetyl-2-furaldehyde; (2) 4-cyanoacetylbenzaldehyde; (3) and (4) 2-cyanoacetyl-5-benzofuraldehyde; (5) 2-cyanoacetyl - 3 - methyl - 5 - benzofuraldehyde; (6) 2-cyanoacetyl-3-phenyl-5-benzofuraldehyde and (7) 2-cyanacetyl-3-methyl-naphtho-(2:1-b) furaldehyde. Many other cyanoacetylaryl groups which may be used are specified.ALSO:The invention comprises acetals derived from alcohols and aldehydes of the formula OHC-R.-CO-CH2-CN. where R is a divalent carbocyclic or heterocyclic aromatic nucleus attached to the CHO and CO groups by carbon atoms forming part of the ring system. The alcohol is a monomeric alcohol of 1-4 C atoms or preferably a monomeric 1:2 or 1:3 alkane diol of 2-4 C atoms or it may be a polymeric hydroxy compound (see Group IV (a)). In the latter cases the acetal group has a cyclic structure. The acetals are prepared by reacting the corresponding acetal of a carboalkoxyaryl aldehyde of the formula OHC-R-COOR1 where R1 is an alkyl group of preferably 1-4 carbon atoms with acetonitrile in the presence of alkali, e.g. sodium methylate. In examples there are prepared by the above process the ethylene glycol acetals of (1) 5-cyanoacetyl-2-furaldehyde; (2) 4-cyanoacetyl benzaldehyde; (3) 2-cyanoacetyl-5-benzofuraldehyde and the dimethyl acetals of (4) 2-cyanoacetyl-5-benzofuraldehyde; (5) 2-cyanoacetyl-3-methyl-5-benzofuraldehyde; (6) 2-cyanoacetyl-3-phenyl-5-benzofuraldehyde; and (7) 2-cyanoacetyl-3-methyl-naphtho-(2:1-b) furaldehyde. Many other carbocyclic and heterocyclic nucleii which may be attached to the CO and acetal groups are specified. Acetals of carboalkoxyaryl aldehydes. The acetals derived from carboalkoxyaryl aldehydes of the formula OHC.R.COOR1 described above are prepared by treating the aldehyde with the corresponding alcohol. Specified acetals are the ethylene glycol acetals of 5-carbomethoxy-2-furaldehyde; 4-carbomethoxybenzaldehyde and 2-carbomethoxy-5-benzofuraldehyde and the dimethyl acetals of 2-carbomethoxy-5-benzofuraldehyde; 2-carbomethoxy-3-methyl-5 - benzofuraldehyde; 2 - carbomethoxy - 3 - phenyl - 5 - benzofuraldehyde and 2 - carbo methoxy-3-methyl-naphtho-(2:1-b) furaldehyde. Carboalkoxyaryl aldehydes of the formula OHC.R.COOR1 are prepared by reacting an ester of a halomethylaryl carboxylic acid with 2-nitropropane in the presence of alkali. The aldehydes specified in the above paragraph are prepared in this way. Alkyl esters of halomethylaryl carboxylic acids are prepared by halomethylating an alkyl ester of an aromatic carboxylic acid, specifically by treating the ester with paraformaldehyde in the presence of zinc chloride and dry hydrogen chloride in a chlorinated methane solvent or by brominating a methyl aryl carboxylic ester. Specified halogenated esters are methyl-5-chloromethylfuroate; methyl- 5 -chloromethylbenzofuran-2-carboxylate; methyl-5-chloromethyl-3-methylbenzofuran-2-carboxylate; methyl-5-bromomethyl-3-phenylbenzofuran-2-carboxylate and methyl chloromethyl- 3 -methylnaphtho - (2:1 - b)-furan-2-carboxylate. Methyl-4-bromo-methylbenzoate is prepared by treating p-toluic acid with thionyl chloride, and brominating the resulting p-toluyl chloride and treating with methanol. Benzofuran-2-carboxylic acids. Ethyl 5-methyl-3-phenylbenzofuran-2-carboxylate is prepared by condensing ethyl-a -chlorobenzoyl acetate with p-cresol. Methyl 3-methyl-naphtho-(2:1-b) furan-2-carboxylate is prepared by condensing a -chloroacetoacetate with b -naphthol. The free acid of the former is obtained by hydrolysis.

  这项发明涉及配方为OHC-R-CO-CH2CN的醛的聚合物缩醛，其中R是通过环系统的碳原子连接到-CO和OHC基团的二价杂环或碳环芳基，与聚合物多羟基醇（例如聚乙烯醇）反应。最好的聚乙烯醇链中每100个碳原子含有至少25个羟基，其中0.75%至10%的羟基被上述一般公式中的醛缩合，0.1%至5%的羟基被含有磺酸基或羧基的醛缩合，例如邻磺基苯甲醛。最好的R是类似苯的碳氢核或含有至少一个氧、硫或氮杂原子的杂环核。这些缩醛是通过将氰乙酰芳基醛（见IV（b）组）的单体缩醛（例如公式中的A是1:2或1:3二醇的残基）与含有大量重复-CH2-CHOH-基团的羟基聚合物反应制备的。在示例中，制备了（1）5-氰乙酰-2-呋喃醛；（2）4-氰乙酰苯甲醛；（3）和（4）2-氰乙酰-5-苯并呋喃醛；（5）2-氰乙酰-3-甲基-5-苯并呋喃醛；（6）2-氰乙酰-3-苯基-5-苯并呋喃醛和（7）2-氰乙酰-3-甲基-萘-(2:1-b)呋喃醛的聚乙烯醇缩醛。还指定了许多其他可用的氰乙酰芳基。此外，该发明涉及由配方为OHC-R.-CO-CH2-CN的醇和醛衍生的缩醛，其中R是通过环系统的碳原子连接到CHO和CO基团的二价碳环或杂环芳基。醇是1-4个碳原子的单体醇，或者更好地是2-4个碳原子的1:2或1:3烷二醇，或者它可以是聚合羟基化合物（见IV（a）组）。在后一种情况下，缩醛基具有环状结构。这些缩醛是通过将配方为OHC-R-COOR1的羧基烷醛的相应缩醛（其中R1是1-4碳原子的烷基）与碱（例如甲基苏打）存在下乙腈反应制备的。在示例中，通过上述过程制备了（1）5-氰乙酰-2-呋喃醛的乙二醇缩醛；（2）4-氰乙酰苯甲醛的乙二醇缩醛；（3）2-氰乙酰-5-苯并呋喃醛的乙二醇缩醛以及（4）2-氰乙酰-5-苯并呋喃醛的二甲基缩醛；（5）2-氰乙酰-3-甲基-5-苯并呋喃醛的二甲基缩醛；（6）2-氰乙酰-3-苯基-5-苯并呋喃醛的二甲基缩醛；以及（7）2-氰乙酰-3-甲基-萘-(2:1-b)呋喃醛的二甲基缩醛。还指定了许多其他可连接到CO和缩醛基的碳环和杂环核。羧基烷醛的缩醛。通过处理上述配方为OHC.R.COOR1的羧基烷醛制备。指定的缩醛是5-羧甲氧基-2-呋喃醛；4-羧甲氧基苯甲醛和2-羧甲氧基-5-苯并呋喃醛的乙二醇缩醛以及2-羧甲氧基-5-苯并呋喃醛的二甲基缩醛；2-羧甲氧基-3-甲基-5-苯并呋喃醛；2-羧甲氧基-3-苯基-5-苯并呋喃醛和2-羧甲氧基-3-甲基-萘-(2:1-b)呋喃醛。通过将卤代甲基芳基羧酸酯与2-硝基丙烷在碱的存在下反应制备配方中指定的羧基烷醛。上述段落中指定的醛以这种方式制备。通过卤代化芳基酸酯的烷基酯卤代化，具体地通过在氯代甲烷溶剂中用氯化锌和干氯化氢处理酯与多甲醛或溴化甲基芳基酸酯溴化制备。指定的卤代酯是甲基-5-氯甲基呋酸酯；甲基-5-氯甲基苯并呋喃-2-羧酸酯；甲基-5-氯甲基-3-甲基苯并呋喃-2-羧酸酯；甲基-5-溴甲基-3-苯基苯并呋喃-2-羧酸酯和甲基氯甲基-3-甲基萘-(2:1-b)-呋喃-2-羧酸酯。通过用亚砜氯处理对甲苯甲酸，溴化所得的对甲苯基氯化物，然后用甲醇处理制备甲基-4-溴甲基苯甲酸酯。苯并呋喃-2-羧酸。通过将乙酰氯苯甲酸乙酯与对甲酚缩合制备乙基-5-甲基-3-苯基苯并呋喃-2-羧酸酯。通过将α-氯乙酰乙酸酯与β-萘酚缩合制备甲基-3-甲基-萘-(2:1-b)呋喃-2-羧酸酯。前者的游离酸可通过水解获得。
• METHOD FOR PROMOTING PLANT GROWTH
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150289512A1

  公开（公告）日：2015-10-15

  The present invention provides a method for promoting plant growth, which comprises treating a plant with at least one compound represented by the following Formula (1) The compounds indicated by formula (1) are used to promote the growth of plants. A plant seed resulting from treating with the compound represented by formula (1) and comprising an effective quantity of the compound represented by formula (1). A composition for promoting plant growth comprising the compound represented by formula (1) and an inactive ingredient.

  本发明提供了一种促进植物生长的方法，包括使用至少一种由以下式（1）表示的化合物处理植物。由式（1）表示的化合物被用于促进植物生长。经由使用由式（1）表示的化合物处理而得到的植物种子，含有由式（1）表示的化合物的有效量。促进植物生长的组合物包括由式（1）表示的化合物和一种无活性成分。