ethyl 3-methyl-5-(methylthio)-1H-pyrazole-4-carboxylate | 65551-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-methyl-5-(methylthio)-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 3-ethyl-5-(methylthio)-1H-pyrazole-4-carboxylate；ethyl 3-methyl-5-methythio-1H-pyrazole-4-carboxylate；3-methyl-5-methylsulfanyl-1(2)H-pyrazole-4-carboxylic acid ethyl ester；ethyl 5-methyl-3-methylsulfanyl-1H-pyrazole-4-carboxylate
• CAS: 65551-57-7
• 化学式: C₈H₁₂N₂O₂S
• mdl: MFCD09881384
• 分子量: 200.261
• InChiKey: XIOMMLQTVVTLJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-5-(methylthio)-1H-pyrazole-4-carboxylate 在 sodium hydroxide 作用下， 生成 3-methyl-5-methylsulfanyl-1(2)H-pyrazole
  参考文献：
  名称：

  Sandstroem, Arkiv foer Kemi, 1955, vol. 8, p. 487,512

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-acetyl-3,3-bis(methylthio)acrylate 在 一水合肼 作用下， 反应 1.0h， 以87%的产率得到ethyl 3-methyl-5-(methylthio)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  在溶剂热条件下由 α-α-二氧环己酮二硫缩醛合成取代的异恶唑和吡唑

  摘要：

  α,α-氧代酮二硫缩醛与盐酸羟胺反应制备了一些新的3,4,5-取代异恶唑、3,4,5和1,3,4,5-取代吡唑；苯肼和水合肼分别在溶剂热条件下，涉及一种环保方法，没有任何环境污染。产率在 71-91% 的范围内。新化合物的结构是通过元素分析、IR、1H NMR 和 13C NMR 确定的。

  DOI：

  10.1080/00397910903459312

文献信息

• Development of a new cascade reaction for convergent synthesis of pyrazolo[1,5-a]quinoline derivatives under transition-metal-free conditions
  作者：Jun-ya Kato、Hiroshi Aoyama、Tsutomu Yokomatsu

  DOI：10.1039/c2ob27050a

  日期：——

  A novel method for the synthesis of pyrazolo[1,5-a]quinolines under the transition-metal-free conditions has been developed. This method involves a novel combination of aromatic nucleophilic substitution and Knoevenagel condensation reactions to give pyrazolo[1,5-a]quinolines.

  研究人员开发了一种在无过渡金属条件下合成吡唑并[1,5-a]喹啉的新方法。该方法通过芳香族亲核取代反应和Knoevenagel缩合反应的独特结合来生成吡唑并[1,5-a]喹啉。
• [EN] BENZOXAZINONE DERIVATIVES AND ANALOGUES THEREOF AS MODULATORS OF TNF ACTIVITY<br/>[FR] DÉRIVÉS DE BENZOXAZINONE ET LEURS ANALOGUES EN TANT QUE MODULATEURS DE L'ACTIVITÉ DU TNF
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2016198400A1

  公开（公告）日：2016-12-15

  A series of substituted 3,4-dihydro-2H-.1,4-benzoxazin-3-one derivatives, and analogues thereof, being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neuradegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列替代的3,4-二氢-2H-1,4-苯并噁嗪-3-酮衍生物及其类似物，作为人类TNFα活性的有效调节剂，因此对于治疗和/或预防各种人类疾病具有益处，包括自身免疫和炎症性疾病；神经和神经退行性疾病；疼痛和伤害感知性疾病；心血管疾病；代谢性疾病；眼部疾病；以及肿瘤性疾病。
• An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring
  作者：Li-Rong Wen、Shu-Wen Wang、Ming Li、Wen-Ying Qi、Xiu-Li Zhang、Hua-Zheng Yang

  DOI：10.1002/jccs.200500143

  日期：2005.10

  protocol has been developed. The acylation reactions were carried out under ultrasound irradiation, and the alkylation reactions were under microwave irradiation and ultrasound irradiation, respectively. Conventional reaction conditions, as well as the use of alpha-bromosubstituted acetophenone (4′) have also been applied in the synthesis of some randomly selected compounds in both series and have generated

  通过 3- 乙基的高度区域选择性酰化和烷基化反应合成了两个系列，共十二个新化合物，1-芳酰基/(芳酰基甲基)-5-甲基-3-甲基硫代吡唑-4-羧酸乙酯 (5/6) 5-甲硫基-1 H-吡唑-4-羧酸甲酯（2a）与芳酰氯（3）和环保试剂α-甲苯磺酰氧基取代的苯乙酮（4），分别开发了绿色方案。酰化反应在超声辐照下进行，烷基化反应分别在微波辐照和超声辐照下进行。常规反应条件以及使用 α-溴代苯乙酮 (4') 也已应用于这两个系列中一些随机选择的化合物的合成中，并相应地生成了相同的化合物。
• Substituted benzo[b][1,4]oxazines and pyrido[3,2-b][1,4]oxazines as modulators of tumor necrosis factor activity
  申请人：UCB Biopharma SPRL

  公开号：US10287299B2

  公开（公告）日：2019-05-14

  A series of substituted 3,4-dihydro-2H-.1,4-benzoxazin-3-one derivatives, and analogs thereof, being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neuradegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列取代的 3,4-二氢-2H-.1,4-苯并恶嗪-3-酮衍生物及其类似物是人类 TNFa 活性的强效调节剂，因此可用于治疗和/或预防各种人类疾病，包括自身免疫和炎症性疾病、神经和神经退行性疾病、疼痛和痛觉失调、心血管疾病、代谢性疾病、眼部疾病和肿瘤疾病。
• Synthesis of poly-substituted pyrazolo[1,5-a]quinolines through one-pot two component cascade reaction
  作者：Jun-ya Kato、Ryosuke Ijuin、Hiroshi Aoyama、Tsutomu Yokomatsu

  DOI：10.1016/j.tet.2014.02.081

  日期：2014.4

  A diversity-oriented method for the synthesis of novel poly-substituted pyrazolo[1,5-a]quinolines has been developed on the basis of an SNAr/Knoevenagel cyclization cascade reaction or an SNAr/Dieckmann- Thorpe cyclization cascade reaction. The methods provide a variety of poly-substituted pyrazolo[1,5-a]quinolines bearing an amino, alkyl or aryl substituent at the 5-position. In addition, a diversity-oriented method for the synthesis of 2-substituted pyrazolo[1,5-a]quinolines from a readily available 2-[[(trifluoromethyl)sulfonyl]oxy]pyrazolo[1,5-a]quinoline has also been disclosed.(C)2014 Elsevier Ltd. All rights reserved.