2-甲基-2H-1,4-苯并噻嗪-3(4H)-酮 | 7028-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 2-甲基-2H-1,4-苯并噻嗪-3(4H)-酮
• 英文名称: 2-methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine
• 英文别名: 2-methyl-3-oxo-2,3-dihydro-4H-1,4-benzothiazine；(+/-)-2-Methyl-2H-1,4-benzothiazin-3(4H)-on；2-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one；2-methyl-2H-1,4-benzothiazin-3(4H)-one；2H-2-methyl-1,4-benzothiazin-3(4H)-one；2-methyl-4H-benzo[1,4]thiazin-3-one；2-methyl-4H-1,4-benzothiazin-3-one
• CAS: 7028-57-1
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: MCEOSIYJRZMQNS-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  350.8±31.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-甲基-2H-1,4-苯并噻嗪-3(4H)-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以49%的产率得到2-甲基-3,4-二氢-2H-1,4-苯并噻嗪
  参考文献：
  名称：

  Eliminative ring fission of 4-acyl-2,3-dihydro-4H-1,4-benzothiazines

  摘要：

  DOI：

  10.1021/jo00170a042
• 作为产物：
  描述：

  2-(1-氯乙基)-1,3-苯并噻唑 在 t-butoxide 作用下， 以 叔丁醇 为溶剂， 以64%的产率得到2-甲基-2H-1,4-苯并噻嗪-3(4H)-酮
  参考文献：
  名称：

  氯烷基苯并噻唑与醇盐的反应

  摘要：

  2-氯烷基苯并噻唑1a-c与醇盐反应生成取代基并进行环扩产物3和4。取代环的扩大竞争很大程度上取决于溶剂，在醇中优选取代反应，而在DMF中则优选环扩大。

  DOI：

  10.1016/s0040-4020(97)00243-3

文献信息

• Heterocyclic aldose reductase inhibitors and methods of using them
  申请人：Carbipem

  公开号：US04755509A1

  公开（公告）日：1988-07-05

  The invention relates to new compounds of the formula: ##STR1## Aldose reductase inhibitors. Treatment of certain complications of diabetes.

  这项发明涉及新化合物，其公式为：##STR1## 醛糖还原酶抑制剂。治疗糖尿病的某些并发症。
• Thermolysis of o-nitro- and 2,4-dinitro-phenoxyacetic acids and related compounds
  作者：R. S. Goudie、P. N. Preston

  DOI：10.1039/j39710001718

  日期：——

  The products of thermolysis of o-nitro- and 2,4-dinitro-phenoxyacetic acids and their sulphur analogues have been investigated. Predominant products from the former include 2H-1,4-benzoxazin-3(4H)-one and derivatives thereof, benzoxazoles, and related compounds. In general, decomposition of the sulphur analogues follows related pathways. The mechanisms of formation of some of the products are considered

  已经研究了邻-硝基-和2,4-二硝基-苯氧基乙酸及其硫类似物的热解产物。前者的主要产物包括2 H -1,4-苯并恶嗪-3（4 H）-one及其衍生物，苯并恶唑和相关化合物。通常，硫类似物的分解遵循相关途径。考虑了某些产物的形成机理。
• 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.
  作者：Hiroyuki TAWADA、Yasuo SUGIYAMA、Hitoshi IKEDA、Yujiro YAMAMOTO、Kanji MEGURO

  DOI：10.1248/cpb.38.1238

  日期：——

  N-Acetic acid derivatives (I) of 2-substituted 1, 4-benzoxazines and benzothiazines were designed and synthesized for evaluation as new aldose reductase inhibitors. In general, 3-thioxo derivatives were more potent inhibitors of aldose reductase from human placenta in vitro than the corresponding 3-oxo derivatives. While many compounds (I) were not very effective in inhibiting sorbitol accumulation in the rat sciatic nerve in vivo, the 3-thioxo compounds bearing an isopropyl group at the 2-position showed highly potent activity in the in vivo assay. Compound 46 (AD-5467) was selected from this series as a candidate for further development.

  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。
• Efficient synthesis of benzene-fused 6/7-membered amides via Xphos Pd G2 catalyzed intramolecular C–N bond formation
  作者：Zhou Xu、Ke Li、Rongliang Zhai、Ting Liang、Xiaodie Gui、Rongli Zhang

  DOI：10.1039/c7ra09160e

  日期：——

  6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald–Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good

  对苯稠6/7元酰胺一种有效的方法通过由一个布赫瓦尔德-哈特维希第二代催化剂的Pd（钯XPHOS G2）催化的芳基氯的分子内酰胺化已研制成功。该催化剂体系使得仅具有适度亲核性的伯酰胺即使在短的反应时间内也能与富电子的芳基氯化物成功地偶联。分子内酰胺化反应还具有良好的化学选择性和优异的官能团相容性。
• 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。