3-乙氧基-2-(甲基磺酰基)丙烯腈 | 104007-26-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 中文名称: 3-乙氧基-2-(甲基磺酰基)丙烯腈
• 英文名称: 3-ethoxy-(2-methylsulfonyl)propenenitrile
• 英文别名: 3-ethoxy-2-methylsulfonyl propenenitrile；3-Ethoxy-2-(methylsulfonyl)acrylonitrile；(E)-3-ethoxy-2-methylsulfonylprop-2-enenitrile
• CAS: 104007-26-3
• 化学式: C₆H₉NO₃S
• 分子量: 175.208
• InChiKey: IVOPUQQPAOLLSH-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3-乙氧基-2-(甲基磺酰基)丙烯腈 在 氨 作用下， 以 水 为溶剂， 生成 3-amino-2-methylsulfonyl propenenitrile
  参考文献：
  名称：

  The isomers and conformers of some push–pull enamines studied by vibrational and NMR spectroscopy and by ab initio calculations

  摘要：

  The isomers and conformers of six push-pull enamines: 3-dimethylamino-, 3-methylamino- and 3-amino-2-acetyl propenenitrile [(H3C)(2)N-CH=C(CN)(COCH3), H3C-NH-CH=C(CN)(COCH3) and H2N-CH=C(CN)(COCH3)] and 3-dimethylamino-, 3-methylamino- and 3-amino-2-methylsulfonyl propenenitrile [(H3C)(2)N-CH=C(CN)(SO2CH3), H3C-NH-CH=C(CN)(SO2CH3) and H2N-CH=C(CN)(SO2CH3)] have been studied experimentally by vibrational and NMR spectroscopy and theoretically by the ab initio calculations at MP2 level in 6-31G** basis set. The IR and Raman spectra of all compounds as a solid and solute in various solvents have been recorded in the region 4000-50 cm(-1). The NMR spectra were obtained in chloroform and DMSO at room temperature.All six compounds have been prepared by the same way. NMR spectra revealed that both dimethylamino compounds were prepared as a pure E isomers whereas in the case of methylamino compounds the 3-methylamino-2-methylsulfonyl propenenitrile was prepared also as a pure E isomer but 3-methylamino-2-acetyl propenenitrile as a pure Z isomer. Also 3-amino-2-methylsulfonyl propenenitrile was obtained as a pure the E isomer, but 3-amino-2-acetyl propenenitrile as a mixture of both E and Z isomers.Confomational possibilities of studied compounds are given only by the rotation of the acetyl and methylamino groups. Vibrational spectra revealed existence of two conformers with Z and E orientation of acetyl group for 3-dimethylamino-2-acetyl propenenitrile. Two conformers with anti or syn orientation of methylamino group for 3-methylamino-2-methylsulfonyl propenenitrile have been confirmed by vibrational and NMR spectra, but only one conformer with anti orientation of methylamino group for 3-methylamino-2-acetyl propenenitrile in chloroform solution and in solid phase was found. For latter compound the additional isomer/conformer was detected in more polar solvents (acetonitrile/DMSO). These experimental findings have been supported by ab initio solvent effect calculations. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.10.053
• 作为产物：
  描述：

  原甲酸三乙酯 、 甲基磺酰乙腈 在 乙酸酐 作用下， 以78%的产率得到3-乙氧基-2-(甲基磺酰基)丙烯腈
  参考文献：
  名称：

  Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones

  摘要：

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.

  DOI：

  10.1021/jm00385a018

文献信息

• Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2-thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles
  作者：Chad E. Stephens、Matthew B. Price、J. Walter Sowell

  DOI：10.1002/jhet.5570360314

  日期：1999.5

  The synthesis of a series of methyl 3-amino-4-aryl(or methyl)sulfonylthiophene-2-carboxylates by reaction of 3-alkoxy-2-aryI(or methyl)sulfonylacrylonitriles with methyl thioglycolate in the presence of triethylamine is described. Hydrolysis/decarboxylation of the ester at the 2-position and acylation of the resulting amine represents a convenient route to 4-arylsulfonyl-3-carboxamidothiophenes. Attempted

  描述了在三乙胺存在下，通过3-烷氧基-2-芳基（或甲基）磺酰基丙烯腈与硫代乙醇酸甲酯的反应，合成一系列3-氨基-4-芳基（或甲基）磺酰基噻吩-2-羧酸甲酯。酯在2-位的水解/脱羧和所得胺的酰化代表了形成4-芳基磺酰基-3-羧酰胺基噻吩的便利途径。在标准条件下尝试酰化标题氨基噻吩未成功。
• Isomers and conformers of two push–pull hydrazines studied by NMR and vibrational spectroscopy and by ab initio calculations
  作者：M. Gróf、J. Polovková、A. Gatial、V. Milata、P. Černuchová、N. Prónayová、P. Mate˘jka

  DOI：10.1016/j.molstruc.2006.10.018

  日期：2007.5

  conformer with intramolecular hydrogen bond for Z -isomer in less polar solvent and next two conformers for E -isomer of DMHAP with Z -orientation of acetyl group and anti and syn orientation of dimethylhydrazine group in more polar solvents. For E -isomer of DMHSP two conformers with anti or syn orientations of dimethylhydrazino group have been also confirmed by NMR spectra in more polar solvents. Additionally

  摘要 两种推拉肼的异构体和构象异构体：3-N , N-二甲基肼基-2-乙酰丙烯腈 [(H 3 C) 2 N NH CH C(CN)(COCH 3 )] (DMHAP) 和 3- N , N-二甲基肼基-2-甲基磺酰基丙烯腈 [(H 3 C) 2 N NH CH C(CN)(SO 2 CH 3 )] (DMHSP) 已通过 NMR 和振动光谱进行了实验研究，并通过从头计算在理论上进行了研究6-31G** 基组中的 MP2 级别。两种化合物作为固体和在各种溶剂中的溶质的 IR 和拉曼光谱已被记录。在室温下在氯仿和 DMSO 中获得 NMR 谱。两种化合物均以相同方式制备。NMR谱显示DMHAP制备为纯Z-异构体，而在DMHSP的情况下获得纯E-异构体。由于这两种化合物的低屏障，实际上在溶液中发生了自由异构化过程，但方向相反。尽管 DMHAP 以固态和极性较小的溶剂中作为 Z 异构体存在，但在极性较大的溶剂中，观察到
• Ethene derivatives
  申请人：MAY & BAKER LIMITED

  公开号：EP0174832A2

  公开（公告）日：1986-03-19

  Ethene derivatives of the general formula: wherein R5 represents a heterocyclyl group, containing 1, 2 or 3 rings and one or more heteroatoms selected from nitrogen, oxygen, sulphur and selenium atoms, which is unsubstituted or substituted by one or more substituents R8 [which may be the same or different and each represents a halogen atom or an amino, carboxy, cyano, nitro, hydroxy, oxo, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzyloxycarbonylamino, sulphamoyl, tetrazol-5-yl, carbamoyl, thiocarbamoyl, arylcarbamoyl or aroyl group, or a straight-or branched-chain alkyl group containing from 1 to 10 carbon atoms, or a straight- or branched-chain alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylsulphamoyl, arylalkyl or arylalkoxy group containing from 1 to 10 carbon atoms in the alkyl moiety, a straight- or branched-chain alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarbamoyl or alkanoylamino group containing from 2 to 6 carbon atoms, an N-benzyloxycarbonyl-N-alkylamino group wherein the alkylamino moiety is straight- or branched-chain and contains from 1 to 6 carbon atoms, or a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group wherein the alkyl moieties may be straight or branched and may each contain from 1 to 6 carbon atoms and may be linked together to form a ring, or a group of the formula -CR4=CR2R3, or an aryl group which is unsubstituted or substituted by one or more substituents RS (as hereinbefore defined), or a heterocyclylalkyl or arylalkyl group wherein the heterocyclyl or aryl moiety is as hereinbefore defined and the alkyl moiety is straight- or branched-chain and contains 1 or 2 carbons atoms, and R1 represents a group of the general formula: wherein R6 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents RS (as hereinbefore defined) or an aryl group which may be substituted by one or more substituents R8 (as hereinbefore defined), or R5 represents a quinonoidal group R7 derived from a nitrogen-containing heterocyclyl group within the definition of R5 as hereinbefore defined, bearing on said ring-nitrogen atom a substituent selected from straight- and branched-chain alkyl groups containing from 1 to 6 carbon atoms which may be substituted by one or more substituents RS (as hereinbefore defined), and aryl groups which may be substituted by one or more substituents RS (as hereinbefore defined), and R1 represents an atom =N-, R4 represents a hydrogen atom or a straight- or branched-chain alkoxy or alkylthio group containing from 1 to 6 carbon atoms, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents R8 (as hereinbefore defined), or an aryl group which may be substituted by one or more substituents R8 (as hereinbefore defined), R2 represents a cyano or formyl group, a straight- or branched-chain alkoxycarbonyl or alkylsulphonyl group containing up to 6 carbons, or a dialkylcarbamoyl or dialkylthiocarbamoyl group wherein the alkyl groups may be the same or different and each may be straight or branched and each contains from 1 to 6 carbon atoms, or an aryloxycarbonyl, arylsulphinyl or arylsulphonyl group wherein the aryl moiety may be substituted by one or more substituents R8 (as hereinbefore defined), R3 represents a group within the definition of R2 or a hydrogen atom or a nitro group or an aryl or aroyl group which may be substituted by one or more substituents R8 (as hereinbefore defined) or a straight- or branched-chain alkanoyl group containing up to 6 carbon atoms, and m and n each represents 1 or 2, and pharmaceutically acceptable salts thereof, with the provisos that the following classes of compounds are excluded:- (i) compounds of formula I wherein R5 represents a pyridyl group which is unsubstituted or substituted by one or more substituents R9 which may be the same or different and each represents a group within the definition of Re other than oxo, straight- or branched-chain alkyl containing from 7 to 10 carbon atoms, straight- or branched-chain alkoxy, alkylthio, alkylsulphonyl, alkylamino, alkylsulphamoyl or arylalkyl containing from 7 to 10 carbon atoms in the alkyl moiety, straight- or branched-chain alkylsulphinyl or arylalkoxy containing from 1 to 10 carbon atoms in the alkyl moiety, or a group -CR4=CR2R3 as hereinbefore defined, R2 and R3 may be the same or different and each represents a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R9 (as hereinbefore defined), R' represents a group of formula II, R4 and R6 represent hydrogen atoms and m and n both represent 1; (ii) compounds of formula I wherein R5 represents a 5-halogenopyrid-2-yl group, R2 and R3 both represent cyano groups, R1 represents a group of formula II, R4 and R° represent hydrogen atoms and m and n both represent 1; and (iii) compounds of formula I wherein R5 represents a 1,2,4-triazolo[4,8-a]-quinoline group which is unsubstituted or substituted by one or more substituents R10 which may be the same or different and each represents a group within the definition of R9 or a straight- or branched-chain alkylsulphinyl group containing from 1 to 6 carbon atoms, R2 and R3 may be the same or different and each represents a cyano group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 6 carbon atoms, or a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R10 (as hereinbefore defined), R' represents a group of formula II, R4 and R6 represent hydrogen atoms and m and n both represent 1, possess useful pharmacological properties.

  以下是对文本的中文翻译： **丙烯衍生物的通式**： 其中，R5代表一个杂环基，包含1、2或3个环，并且含有1个或多个选自氮、氧、硫和硒原子的杂原子，该杂环基可以是未取代的，或被一个或多个R8取代基取代（R8可以相同或不同，每个R8代表一个卤素原子；或者一个氨基、羧基、氰基、硝基、羟基、羰基、甲酰基、三氟甲基、芳基、芳氧基、芳硫基、苄氧羰基氨基、硫脲基、5-四唑基、羰基氨基、硫代羰基氨基、芳基羰基氨基或芳酰基；或者一个直链或支链烷基，含有1至10个碳原子；或者一个直链或支链烷氧基、烷硫基、烷亚砜基、烷砜基、烷氨基、烷硫脲基、芳基烷基或芳基烷氧基，其中烷基部分含有1至10个碳原子；或者一个直链或支链烷酰基、烷氧基羰基、烷氧基羰基氨基、烷基羰基氨基或烷酰基氨基，含有2至6个碳原子；或者一个N-苄氧羰基-N-烷基氨基，其中烷基氨基部分为直链或支链，含有1至6个碳原子；或者一个二烷基硫脲基、二烷基氨基或二烷基羰基氨基，其中烷基部分可以为直链或支链，每个烷基部分含有1至6个碳原子，且烷基部分可以彼此连接形成一个环；或者一个通式为-CR4=CR2R3的基团；或者一个未取代的芳基，或被一个或多个R8取代基取代的芳基；或者一个杂环基烷基或芳基烷基，其中杂环基或芳基部分如前所定义，烷基部分为直链或支链，含有1或2个碳原子）。 R1代表一个通式为的基团： 其中，R6代表一个氢原子；或一个直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 此外，R5还可以代表一个由含氮杂环基衍生而来的醌状基团R7，该杂环基如前所定义的R5，其中环氮原子上取代有一个选自以下的基团：直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 R1代表一个=NH原子；R4代表一个氢原子，或一个直链或支链烷氧基、烷硫基，含有1至6个碳原子；或一个三氟甲基基团；或一个直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 R2代表一个氰基或甲酰基；或一个直链或支链烷氧基羰基或烷硫基，含有不超过6个碳原子；或一个二烷基羰基氨基或二烷基硫代羰基氨基，其中两个烷基可以相同或不同，每个烷基为直链或支链，含有1至6个碳原子；或一个芳氧基羰基、芳硫基或芳硫基羰基，其中芳基部分可以被一个或多个R8取代基取代（如前所定义）。 R3代表一个与R2定义范围内的基团，或一个氢原子；或一个硝基；或一个芳基；或一个芳酰基，可以被一个或多个R8取代基取代（如前所定义）；或一个直链或支链烷酰基，含有不超过6个碳原子。 m和n各自代表1或2。 除以下化合物类别外，上述结构及其药学上可接受的盐类具有有用的药理学性质： (i) 通式为I的化合物，其中R5代表一个吡啶基，该吡啶基可以是未取代的，或被一个或多个R9取代基取代，R9可以相同或不同，每个R9代表一个基团，其定义范围包括：R8（但不包括氧代基、直链或支链烷基，含有7至10个碳原子；直链或支链烷氧基、烷硫基、烷硫基、烷氨基、烷硫脲基、或芳基烷基，其中烷基部分含有7至10个碳原子；直链或支链烷亚砜基，或芳基烷氧基，其中烷基部分含有1至10个碳原子）；或一个如前所定义的-CR4=CR2R3基团。其中，R2和R3可以相同或不同，各自代表一个苯硫基，可以是未取代的，或被一个或多个R9取代基取代（如前所定义）。R’代表一个通式II的基团。R4和R6代表氢原子，m和n均为1。 (ii) 通式为I的化合物，其中R5代表一个5-卤素取代吡啶-2-基，R2和R3均为氰基，R1代表一个通式II的基团，R4和R°代表氢原子，m和n均为1。 (iii) 通式为I的化合物，其中R5代表一个1,2,4-三唑[4,8-a]-喹啉基，该基团可以是未取代的，或被一个或多个R10取代基取代，R10可以相同或不同，每个R10代表一个基团，其定义范围包括：R9（如前所定义），或一个直链或支链烷亚砜基，含有1至6个碳原子。R2和R3可以相同或不同，各自代表一个氰基、一个直链或支链烷氧基羰基（含有2至6个碳原子），或一个苯硫基，可以是未取代的，或被一个或多个R10取代基取代（如前所定义）。R’代表一个通式II的基团。R4和R6代表氢原子，m和n均为1。 上述化合物在排除了特定结构后，具有有用的药理学性质。
• LUNT E.; NEWTON CH. G.; SMITH CH.; STEVENS G. P.; STEVENS M. F. G.; STRAW+, J. MED. CHEM., 30,(1987) N 2, 357-366
  作者：LUNT E.、 NEWTON CH. G.、 SMITH CH.、 STEVENS G. P.、 STEVENS M. F. G.、 STRAW+

  DOI：——

  日期：——
• PROCESS FOR PRODUCING 5-AMINOPYRAZOLE DERIVATIVE, AND AZO DYE
  申请人：Tateishi Keiichi

  公开号：US20100063262A1

  公开（公告）日：2010-03-11

  A process for producing a 5-aminopyrazole derivative represented by Formula (I) includes a step of reacting a hydrazine compound represented by Formula (II) with a compound represented by Formula (III) under a condition satisfying Reaction Condition 1 and Reaction Condition 2, wherein Reaction Condition 1 is that the reaction is conducted in a reaction solvent containing water, and Reaction Condition 2 is that pH of a liquid mixture containing the hydrazine compound represented by Formula (II), the compound represented by Formula (III), the reaction solvent, and an acidifying agent upon charging is within a range of from 2.0 to 4.0 at 25° C.: wherein the symbols in the formulae (I) to (III) are defined in the specification.