(4H-benzo[1,4]thiazin-3-ylidene)-acetic acid ethyl ester | 66155-34-8

• 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: (4H-benzo[1,4]thiazin-3-ylidene)-acetic acid ethyl ester
• 英文别名: Acetic acid, (2H-1,4-benzothiazin-3(4H)-ylidene)-, ethyl ester；ethyl 2-(4H-1,4-benzothiazin-3-ylidene)acetate
• CAS: 66155-34-8
• 化学式: C₁₂H₁₃NO₂S
• mdl: MFCD05670500
• 分子量: 235.307
• InChiKey: ZVUNXUBYWPNSIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4H-benzo[1,4]thiazin-3-ylidene)-acetic acid ethyl ester 、 1-benzyl-5-chloro-3-hydroxy-3-(1H-indol-3-yl)indolin-2-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以42%的产率得到ethyl 1-benzyl-5-chloro-2-oxo-12',12b'-dihydro-5'H-spiro[indoline-3,7'-indolo[3,2-c]phenothiazine]-6'-carboxylate
  参考文献：
  名称：

  酸促进3-羟基-3-（吲哚-3-基）吲哚-2-酮与环状巯基取代的β-烯胺酯的多米诺反应的分子多样性

  摘要：

  乙酸促进的3-羟基-3-（吲哚-3-基）吲哚-2-酮与巯基取代的β-烯胺酸酯的反应显示出非常有趣的分子多样性。在室温下，在乙酸的存在下，在乙醇中的反应以高收率得到两个非对映异构体3,3-二取代的羟吲哚。当反应在回流的乙醇中进行时，与具有N-烷基的3-羟基-3-（吲哚-3-基）吲哚-2-酮的反应以令人满意的产率得到了多环螺并恶多尔。然而，与带有NH基团的3-羟基-3-（吲哚-3-基）吲哚-2-酮的类似反应提供了官能化的二氢吲哚[3,2- c]吩噻嗪类化合物，其羟吲哚依次开环。合理地提出了一种可行的多米诺环化机理，以形成不同种类的多环化合物。

  DOI：

  10.1039/d1nj00947h
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 2-氨基苯硫醇 在 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 生成 (4H-benzo[1,4]thiazin-3-ylidene)-acetic acid ethyl ester
  参考文献：
  名称：

  Non-nucleoside inhibitors of HCV polymerase NS5B. Part 2: Synthesis and structure–activity relationships of benzothiazine-substituted quinolinediones

  摘要：

  A new series of benzothiazine-substituted quinolinediones were evaluated as inhibitors of HCV polymerase NS5B. SAR studies on this series revealed a methyl sulfonamide group as a high affinity feature. Analogues with this group showed submicromolar potencies in the HCV cell based replicon assay. Pharmacokinetic and toxicology studies were also performed on a selected compound (34) to evaluate in vivo properties of this new class of inhibitors of HCV NS5B polymerase.

  DOI：

  10.1016/j.bmcl.2009.05.004

文献信息

• Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino Esters, Isatins, and Cyclic 1,3-Diketones
  作者：Quan-Shun Sun、Jing Sun、Liu-Na Pan、Chao-Guo Yan

  DOI：10.1021/acs.joc.0c01290

  日期：2020.10.2

  three-component reaction of alkyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro[indeno[1,2-b]phenothiazine-6,3′-indolines] or spiro[cyclopenta[b]phenothiazine-4,3′-indolines] in good yields and with high diastereoselectivity. More interestingly, a similar three-component reaction with 4-

  乙酸存在下，2-（苯并[ b ] [1,4]噻嗪-3-亚烷基）乙酸烷基酯，靛红和1,3-茚满二酮（1,3-环戊二酮）在乙醇中的三组分反应可方便地以高收率和高非对映选择性获得螺[茚并[1,2 - b ]吩噻嗪-6,3'-二氢吲哚]或螺[环戊[ b ]吩噻嗪-4,3'-二氢吲哚]。更有趣的是，与4-羟基铬-2-二烯类似的三组分反应导致了意想不到的多环螺[苯并[ b ]铬基[3'，4'：5,6]吡喃并[2,3- e] [1,4]噻嗪-7,3'-二氢吲哚]的产率令人满意。合理地提出了一种合理的反应机理来形成不同种类的螺环化合物，并且清楚地阐明了各种螺环化合物的立体化学。
• Non-nucleoside inhibitors of HCV NS5B polymerase. Part 1: Synthetic and computational exploration of the binding modes of benzothiadiazine and 1,4-benzothiazine HCV NS5b polymerase inhibitors
  作者：Robert T. Hendricks、Jay B. Fell、James F. Blake、John P. Fischer、John E. Robinson、Stacey R. Spencer、Peter J. Stengel、April L. Bernacki、Vincent J.P. Leveque、Sophie Le Pogam、Sonal Rajyaguru、Isabel Najera、John A. Josey、Jason R. Harris、Steven Swallow

  DOI：10.1016/j.bmcl.2009.04.119

  日期：2009.7

  The importance of internal hydrogen bonding in a series of benzothiadiazine and 1,4-benzothiazine NS5b inhibitors has been explored. Computational analysis has been used to compare the protonated vs. anionic forms of each series and we demonstrate that activity against HCV NS5b polymerase is best explained using the anionic forms. The syntheses and structure-activity relationships for a variety of new analogs are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Non-nucleoside inhibitors of HCV polymerase NS5B. Part 2: Synthesis and structure–activity relationships of benzothiazine-substituted quinolinediones
  作者：Javier de Vicente、Robert T. Hendricks、David B. Smith、Jay B. Fell、John Fischer、Stacey R. Spencer、Peter J. Stengel、Peter Mohr、John E. Robinson、James F. Blake、Ramona K. Hilgenkamp、Calvin Yee、George Adjabeng、Todd R. Elworthy、Jahari Tracy、Elbert Chin、Jim Li、Beihan Wang、Joe T. Bamberg、Rebecca Stephenson、Connie Oshiro、Seth F. Harris、Manjiri Ghate、Vincent Leveque、Isabel Najera、Sophie Le Pogam、Sonal Rajyaguru、Gloria Ao-Ieong、Ludmila Alexandrova、Susan Larrabee、Michael Brandl、Andrew Briggs、Sunil Sukhtankar、Robert Farrell、Brian Xu

  DOI：10.1016/j.bmcl.2009.05.004

  日期：2009.7

  A new series of benzothiazine-substituted quinolinediones were evaluated as inhibitors of HCV polymerase NS5B. SAR studies on this series revealed a methyl sulfonamide group as a high affinity feature. Analogues with this group showed submicromolar potencies in the HCV cell based replicon assay. Pharmacokinetic and toxicology studies were also performed on a selected compound (34) to evaluate in vivo properties of this new class of inhibitors of HCV NS5B polymerase.
• Molecular diversity of the acid promoted domino reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and cyclic mercapto-substituted β-enamino esters
  作者：Liu-Na Pan、Qing Wang、Jing Sun、Quan-Shun Sun、Chao-Guo Yan

  DOI：10.1039/d1nj00947h

  日期：——

  The acetic acid promoted reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and mercapto-substituted β-enamino esters showed very interesting molecular diversity. The reaction in ethanol at room temperature in the presence of acetic acid resulted in two diastereoisomeric 3,3-disubstituted oxindoles in high yields. When the reaction was carried out in refluxing ethanol, the reaction with 3-hydroxy-

  乙酸促进的3-羟基-3-（吲哚-3-基）吲哚-2-酮与巯基取代的β-烯胺酸酯的反应显示出非常有趣的分子多样性。在室温下，在乙酸的存在下，在乙醇中的反应以高收率得到两个非对映异构体3,3-二取代的羟吲哚。当反应在回流的乙醇中进行时，与具有N-烷基的3-羟基-3-（吲哚-3-基）吲哚-2-酮的反应以令人满意的产率得到了多环螺并恶多尔。然而，与带有NH基团的3-羟基-3-（吲哚-3-基）吲哚-2-酮的类似反应提供了官能化的二氢吲哚[3,2- c]吩噻嗪类化合物，其羟吲哚依次开环。合理地提出了一种可行的多米诺环化机理，以形成不同种类的多环化合物。