2-propyl-2H-1,4-benzothiazin-3(4H)-one | 91132-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-propyl-2H-1,4-benzothiazin-3(4H)-one
• 英文别名: 2-propyl-4H-benzo[1,4]thiazin-3-one；2-propyl-2H-benzo[b][1,4]thiazin-3(4H)-one；2H-1,4-Benzothiazin-3(4H)-one, 2-propyl-；2-propyl-4H-1,4-benzothiazin-3-one
• CAS: 91132-38-6
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: HYPGKVVWNUUUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-propyl-2H-1,4-benzothiazin-3(4H)-one 、 溴乙酸甲酯 生成 (2-Propyl-3-thioxo-2,3-dihydro-benzo[1,4]thiazin-4-yl)-acetic acid
  参考文献：
  名称：

  Studies on antidiabetic agents. IX. A new aldose reductase inhibitor, AD-5467, and related 1,4-benzoxazine and 1,4-benzothiazine derivatives: Synthesis and biological activity.

  摘要：

  N-乙酸衍生物（I）的2-取代基1,4-苯并恶嗪和苯并噻嗪被设计合成，以评估其作为新型醛糖还原酶抑制剂的潜力。一般而言，3-硫代羰基衍生物在体外对人胎盘醛糖还原酶的抑制活性比相应的3-氧代衍生物更强。虽然许多化合物（I）在体内对大鼠坐骨神经山梨醇积累的抑制作用并不十分有效，但在体内试验中，2-位带有异丙基的3-硫代羰基化合物显示出极强的活性。从这一系列中选出化合物46（AD-5467）作为进一步开发的候选药物。

  DOI：

  10.1248/cpb.38.1238
• 作为产物：
  描述：

  2-溴戊酸甲酯 、 2-氨基苯硫醇 生成 2-propyl-2H-1,4-benzothiazin-3(4H)-one
  参考文献：
  名称：

  TAWADA, HIROYUKI;SUGIYAMA, YASUO;IKEDA, HITOSHI;YAMAMOTO, YUJIRO;MEGURO, +, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1238-1245

  摘要：

  DOI：

文献信息

• Regioselective one pot synthesis of 2-alkyl/aryl-4<i>h</i>-benzo[1,4] thiazine-3-one<i>via</i>microwave irradiation
  作者：Sukanta Kamila、Benjamin Koh、Omair Khan、Hongming Zhang、Edward R. Biehl

  DOI：10.1002/jhet.5570430632

  日期：2006.11

  A series of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3-ones have been synthesized by microwave irradiation of ethyl-2-bromo-2-alkyl/aryl acetate and 2-amino thiophenol in the presence of 1,8-diazabicyclo-[5.4.0] undec-7-ene and N-methylpiperidine. All compounds were characterized by 1H NMR, 13C NMR and elemental analyses, and by X-ray crystallography in the case of 2-methyl-4H-benzo[1,4]thiazin-3-one.

  在存在下，通过微波辐射乙基-2-溴-2-烷基/乙酸芳基酯和2-氨基苯硫酚合成了一系列2-烷基/芳基-4 H-苯并[1,4]噻嗪-3-酮1,8-二氮杂双环-[5.4.0]十一烷基-7-烯和N-甲基哌啶。对于2-甲基-4 H-苯并[1,4]噻嗪-3-酮，所有化合物的特征在于1 H NMR，13 C NMR和元素分析，以及X射线晶体学。
• [Omim][NO₃], a Green and Base-Free Medium for One-Pot Synthesis of Benzothiazinones at Room Temperature
  作者：Ali Sharifi、M. Saeed Abaee、Mahdiyeh Rouzgard、Mojtaba Mirzaei

  DOI：10.1080/00397911.2012.687422

  日期：2013.8.3

  Abstract A general and efficient room-temperature procedure is developed for high-yield synthesis of 2H-benzo[b][1,4]thiazin-3(4H)-one derivatives in one pot from the reaction of 2-aminothiophenols with 2-bromoalkanoates in ionic liquid [bmim]NO3 without the use of any catalyst, base, or additive. Products were obtained in good yields by simple extraction with Et2O followed by evaporation of the volatile

  摘要 开发了一种通用且高效的室温方法，用于通过 2-氨基苯硫酚与 2-溴代链烷酸酯在离子液体 [bmim]NO3 中，无需使用任何催化剂、碱或添加剂。通过用 Et2O 简单萃取，然后蒸发挥发物并从 Et2O 中重结晶，可以得到高产率的产物。离子液体在不损失其活性的情况下循环使用并在下一步反应中重复使用。图形概要
• [DE] SUBSTITUIERTE HETEROCYCLEN UND DEREN VERWENDUNG IN ARZNEIMITTELN<br/>[EN] SUBSTITUTED HETEROCYCLES AND THEIR USE IN MEDICAMENTS<br/>[FR] HETEROCYCLIQUES SUBSTITUES ET LEUR UTILISATION DANS DES MEDICAMENTS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1998050372A1

  公开（公告）日：1998-11-12

  (DE) Es werden Verbindungen der Formel (I) beschrieben, deren Herstellung und Verwendung in Arzneimitteln.(EN) The invention relates to compounds of formula (I), to the production of said compounds and their use in medicaments.(FR) L'invention concerne des composés de la formule (I), leur production et leur utilisation dans des médicaments.

  （德）描述了式 (I) 的化合物，及这些化合物的制备和药用用途。（英）本发明涉及式 (I) 化合物，及其制备及其用于医药品。（法）涉及式 (I) 化合物的发明，这些化合物的制备和药用用途。
• Synergistic promoting effect of ball milling and KF–alumina support for the green synthesis of benzothiazinones
  作者：Ali Sharifi、Mohammad Ansari、Hossein Reza Darabi、M. Saeed Abaee

  DOI：10.1016/j.tetlet.2015.12.078

  日期：2016.2

  A solvent-free procedure was developed for the reaction of 2-aminothiophenols with 2-bromoalkanoates, where KF-Al2O3 support and ball milling cooperatively lead to a green and efficient synthesis of several benzothiazinone derivatives in good to excellent yields. The catalyst could be recycled in further reactions while maintaining its activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of some 2-alkyl-2H-1,4-benzothiazin-3(4H)-ones and 2-alkylbenzo[d]imidazolo[2,1-b]-thiazolidin-3-ones
  作者：M. Koóš

  DOI：10.1007/bf00812716

  日期：1994.8

  Sodium 2-aminothiophenoxide (1) reacts with ethyl 2-bromoalkanoates (2) under direct cyclization to form 2-alkyl-2H-1,4-benzothiazin-3(4H)-ones (3). Reaction of the sodium salt of 2-mercaptobenzimidazole (4) with 2 or 2-bromoalkanoic acids (5) affords only S-alkylated products (6 or 7, respectively). The cyclization products - 2-alkylbenzo[d] imidazolo[2,1-b]thiazolidin-3-ones (8)- can be obtained only from the corresponding 2-(2-benzimidazolylthio)alkanoic acids (7) by the action of acetic anhydride. Both compounds 3 and 8 exhibit only moderate antimicrobial activity against some gram-positive bacteria.