3-oxo-3-(5-methylthiophene-2-yl)propanenitrile | 71683-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-3-(5-methylthiophene-2-yl)propanenitrile
• 英文别名: 3-(5-Methylthiophen-2-yl)-3-oxopropanenitrile
• CAS: 71683-03-9
• 化学式: C₈H₇NOS
• mdl: MFCD09931289
• 分子量: 165.216
• InChiKey: GNSZJJGFNAFOSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-3-(5-methylthiophene-2-yl)propanenitrile 在 羟胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 14.0h， 以71%的产率得到3-(5-methylthiophen-2-yl)-1,2-oxazol-5-amine
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018
• 作为产物：
  描述：

  2-bromo-1-(5-methylthiophen-2-yl)-ethan-1-one 、 氰化钠 以34%的产率得到
  参考文献：
  名称：

  RIDGE D. N.; HANIFIN J. W.; HARTEN L. A.; JOHNSON B. D.; MENSCHIK J.; NIC+, J. MED. CHEM., 1979, 22, NO 11, 1385-1389

  摘要：

  DOI：

文献信息

• SUBSTANCES FOR DYEING KERATINOUS FIBERS
  申请人：Gross Wibke

  公开号：US20100037909A1

  公开（公告）日：2010-02-18

  Disclosed are substances which contain unsaturated, non-aromatic dialdehydes of formula (Ia) and/or the tautomer (Ib) thereof, wherein R 1 , R 2 , and R 3 are defined as indicated in claim 1 , along with at least one CH-acidic compound of formulas (II) and/or (III), wherein R 6 , R 7 , R 8 , R 9 , R 10 , Y, X − , Het, and X 1 are defined as indicated in claim 1 , in a cosmetic carrier. Said substances color keratinous fibers, especially human hair, in an intensive, colorfast, natural brown shade.

  本发明涉及一种含有式(Ia)和/或其互变异构体(Ib)的不饱和非芳香二醛的物质，其中R1、R2和R3如权利要求1所示定义，以及至少一种式(II)和/或(III)的CH-酸性化合物，其中R6、R7、R8、R9、R10、Y、X−、Het和X1如权利要求1所示定义，在一种化妆品载体中。所述物质能够使角质纤维，尤其是人类头发，在一种浓郁、色牢、自然棕色的色调中着色。
• AGENT FOR DYEING KERATIN-CONTAINING FIBERS
  申请人：Gross Wibke

  公开号：US20100064450A1

  公开（公告）日：2010-03-18

  The invention relates to an agent for dying fibers comprising keratin, particularly human hair, the agent comprising at least one compound of the formula: together with at least one CH-acidic compound. The invention also relates to methods for shading oxidation dyed fibers, methods for freshening up fibers, methods for making an agent for dyeing fibers and to various compositions.

  该发明涉及一种用于染色纤维的药剂，包括角蛋白，特别是人类头发，该药剂包括至少一种具有以下结构的化合物：以及至少一种CH-酸性化合物。该发明还涉及用于给氧化染色纤维着色的方法，用于使纤维焕发的方法，用于制备染色纤维药剂的方法以及各种组合物。
• Manganese(III)-Based Facile Synthesis of 3-Cyano-4,5-dihydrofurans and 4-Cyano-1,2-dioxan-3-ols Using Alkenes and Acylacetonitrile Building Blocks
  作者：Van-Ha Nguyen、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1055/s-1997-1282

  日期：1997.8

  New 3-cyano-4,5-dihydrofurans and 4-cyano-1,2-dioxan-3-ols were alternatively synthesized in good yields by the oxidation of acylacetonitrile building blocks with manganese(III) acetate in the presence of alkenes without any byproducts. The reaction at reflux temperature gave 3-cyano-4,5-dihydrofurans under an argon atmosphere, while 4-cyano-1,2-dioxan-3-ols were obtained at 23°C under an air atmosphere except for the reaction of styrene with benzoylacetonitrile which afforded 2-cyano-1,4-diphenylbutane-1,4-dione, and the reaction of 1,1,-diphenylethene with 2-(2-cyano-1-oxoethyl)-5-methylfuran which yielded 2-cyano-4,4-diphenylbutanolide without any cyclic peroxides. The oxidation of benzoylacetonitrile itself at 23°C under an air atmosphere in the absence of alkene gave benzoic acid. Easy conversion of the 1,2-dioxanes to furans was demonstrated, and mechanisms for the formation of dihydrofurans and dioxans as well as the unusual transformation to butanedione and butanolide were also discussed.

  新型3-氰基-4,5-二氢呋喃和4-氰基-1,2-二氧杂环-3-醇通过在烯烃存在下，用醋酸锰(III)对酰基乙腈构建块进行氧化，获得了良好产率且没有副产物。回流温度下的反应在氩气气氛中生成3-氰基-4,5-二氢呋喃，而在空气气氛下23°C下反应则获得4-氰基-1,2-二氧杂环-3-醇，除了苯甲基乙腈与苯乙烯的反应生成了2-氰基-1,4-二苯基丁-1,4-二酮，以及1,1-二苯乙烯与2-(2-氰基-1-氧代乙基)-5-甲基呋喃的反应生成2-氰基-4,4-二苯基丁内酯，没有生成任何环状过氧化物。苯甲基乙腈本身在空气气氛下23°C的氧化反应在缺乏烯烃的情况下产生了苯甲酸。还展示了1,2-二氧杂环转化为呋喃的简便过程，同时讨论了二氢呋喃和二氧杂环的形成机制，以及向丁二酮和丁内酯的不寻常转化。
• Simple Synthesis of 3-Oxopropanenitriles<i>via</i>Electrophilic Cyanoacetylation of Heterocycles with Mixed Anhydrides
  作者：Anita Andicsovà-Eckstein、Erika Kozma、Daniel Végh

  DOI：10.1002/jhet.2511

  日期：2016.11

  simple and efficient method for the synthesis of 3‐oxopropanenitriles from variously substituted heterocyclic compounds via direct electrophilic cyanoacetylation is described. A series of heterocyclic 3‐oxopropanenitriles (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j, 2k) have been synthesized using mixed anhydride (acetic or trifluoroacetic anhydride:cyanoacetic acid) in the presence of Mg(ClO4)2·2H2O as

  描述了一种通过直接亲电氰基乙酰化从各种取代的杂环化合物合成3-氧代丙烷腈的简单有效的方法。在Mg的存在下，使用混合酸酐（乙酸酐或三氟乙酸酐：氰基乙酸）合成了一系列杂环3-氧代丙烷腈（2a，2b，2c，2d，2e，2f，2g，2h，2i，2j，2k） （ClO 4）2 ·2H 2以O为催化剂。该方法也可扩展为贫电子芳香族化合物的氰基乙酰化。
• Lightening Agents and/or Dyes that Contain Aldehyde(s)
  申请人：Höffkes Horst

  公开号：US20100278767A1

  公开（公告）日：2010-11-04

  Agents for dyeing and/or lightening keratin fibers, in particular human hair, containing, relative to the weight thereof, 0.001 to 15 wt. % of at least one aldehyde of the formula (I): wherein X represents —CH(R 2 )—SO 2 —Y—R 1 , —CR 3 R 4 R 5 , or wherein Y represents —CH(CHO)— or —CH 2 — or a chemical bond, and wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 independently represents —H or —CN or —F or —Cl or —Br or —I or —CHO or —NH 2 or —NO 2 or —CF 3 or —CCl 3 or —CF 2 CF 3 or —CCl 2 CCl 3 or an optionally substituted (C 1 -C 6 ) alkyl group or a hydroxyalkyl group or a polyhydroxyalkyl group or an optionally substituted (C 1 -C 6 ) alkylene group, and wherein the agent contains no oxidation dye precursors of developer and coupler type.

  含有相对于其重量0.001至15重量%的至少一种醛类化合物的染色和/或漂白角蛋白纤维的制剂，特别是人类头发。其中该醛类化合物的化学式为(I)：其中X代表—CH(R2)—SO2—Y—R1，—CR3R4R5，或其中Y代表—CH(CHO)—或—CH2—或化学键，且其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10独立地代表—H或—CN或—F或—Cl或—Br或—I或—CHO或—NH2或—NO2或—CF3或—CCl3或—CF2CF3或—CCl2CCl3或一个可选择取代的（C1-C6）烷基或一个羟烷基或一个多羟基烷基或一个可选择取代的（C1-C6）亚烷基，且该制剂不含氧化染料的氧化剂和偶联剂类型的前体。