7-bromo-1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide | 1031684-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 7-bromo-1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide
• 英文别名: N-methoxy-7-bromo-3,4-dihydro-2,1-benzothiazine-2,2-dioxide；7-Bromo-1-methoxy-3,4-dihydro-2lambda6,1-benzothiazine 2,2-dioxide；7-bromo-1-methoxy-3,4-dihydro-2λ6,1-benzothiazine 2,2-dioxide
• CAS: 1031684-27-1
• 化学式: C₉H₁₀BrNO₃S
• 分子量: 292.153
• InChiKey: MCZATASUCLNZEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-bromophenyl)-N-methoxyethanesulfonamide 在 碘苯 、 间氯过氧苯甲酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 2.0h， 以60%的产率得到7-bromo-1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide
  参考文献：
  名称：

  Iodobenzene-Catalyzed Preparation of 3,4-Dihydro-1H-2,1-benzothiazine 2,2-Dioxides from 2-Aryl-N-methoxyethanesulfonamides with m-Chloro­peroxybenzoic Acid

  摘要：

  在碘苯催化下，2-芳基-N-甲氧基乙烷磺酰胺与间氯过氧苯甲酸发生环化反应，生成相应的 1-甲氧基-3,4-二氢-1H-2,1-苯并噻嗪 2,2-二氧杂化物，收率中等至良好。在该反应中，原位形成的活性高价碘[(羟基)(对甲苯磺酰氧基)碘]苯与 2-芳基-N-甲氧基乙烷磺酰胺在芳香环上发生亲电反应，生成相应的 1-甲氧基-3,4-二氢-1H-2,1-苯并噻嗪 2,2-二氧化物。

  DOI：

  10.1055/s-2008-1042945

文献信息

• Novel Preparation of Polymer-Supported Iodobenzene and Its Synthetic Utility as a Recyclable Reagent with m-Chloroperbenzoic Acid
  作者：Hideo Togo、Yuhsuku Suzuki

  DOI：10.1055/s-0029-1218795

  日期：2010.7

  Three novel polymer-supported iodobenzene compounds A0, A6, and A10 were prepared from the reaction of commercially available cross-linked poly(p-chloromethyl)styrene with m-iodobenzylalcohol, 6-(m-iodobenzyloxy)-1-hexanol, and 10-(m-iodobenzyloxy)-1-decanol. Their catalytic reactivity and reusability for the oxidative α-tosyloxylation of ketones and the cyclization of N-methoxy-2-arylethanesulfonamides

  三种新型聚合物负载的碘苯化合物A 0，A 6和A 10从可商购的交联聚（的反应制备p氯甲基）苯乙烯与米-iodobenzylalcohol，6-（米-iodobenzyloxy）-1-己醇和10-（米-iodobenzyloxy）-1-癸醇。它们对酮的氧化α-对甲苯磺酰和的环化催化活性和可重用性Ñ在存在甲氧基-2- arylethanesulfonamides米氯过苯甲酸（米CPBA）被证实提供α-tosyloxyketones和Ñ-甲氧基-3,4-二氢-2,1-苯并噻嗪-2,2-二氧化物的收率很高。 聚合物支撑的Φ -再循环米CPBA - α-tosyloxyketone -酮- ñ -甲氧基-3,4-二氢-2,1-苯并噻嗪2,2-二氧化物-催化剂
• Iodoarene-Mediated Cyclization of N-Methoxy-2-arylethanesulfonamides with Oxone
  作者：Hideo Togo、Yuhsuke Suzuki、Yoshihide Ishiwata

  DOI：10.3987/com-10-s(e)4

  日期：——

  Iodoarene-mediated cyclization of N-methoxy-2-arylethanesulfonamides with Oxone (R) was carried out to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in moderate to good yields in acetonitrile. In this reaction, reactive hypervalent iodine species, i.e., [(hydroxy)(tosyloxy)iodo]arenes, were formed in situ and reacted with N-methoxy-2-arylethanesulfonamides to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in an electrophilic manner on the aromatic ring. Ion-supported PhI could be also used for the same cyclization of N-methoxy-2-arylethanesulfonamides with Oxone to provide N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in good to moderte yields. However, ion-supported PhI could not be reused for the same reaction. The same iodoarene-mediated cyclization of N-methoxy-3-phenylpropanamide and N-methoxy-4-phenylbutanamide with Oxone was also carried out to form the corresponding N-methoxybenzolactams in moderate yields.
• Ion-supported PhI-catalyzed cyclization of N-methoxy-2-arylethanesulfonamides with mCPBA
  作者：Yoshihide Ishiwata、Hideo Togo

  DOI：10.1016/j.tetlet.2009.07.034

  日期：2009.9

  The ion-supported PhI-catalyzed cyclization of N-methoxy-2-arylethanesulfonamides with mCPBA was carried out to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in moderate to good yields in 2,2,2-trifluoroethanol. Here, reactive hypervalent iodine compounds, that is, ion-supported [(hydroxy)(tosyloxy)iodo]benzenes, were formed in situ and reacted with N-methoxy-2-arylethanesulfonamides to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in an electrophilic manner on the aromatic ring. Moreover, ion-supported Phi could be efficiently reused to provide the products in good yields. The same ion-supported PhI-catalyzed cyclization of N-methoxy-3-phenylpropionamide and N-methoxy-4-phenylbutyramide with mCPBA was carried out to form the corresponding N-methoxy benzolactams in moderate yields in 2,2,2-trifluoroethanol. (C) 2009 Elsevier Ltd. All rights reserved.