N-methoxy-2,2-dioxo-2λ⁶-thia-1-aza-spiro[4.5]deca-6,9-dien-8-one | 593288-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-methoxy-2,2-dioxo-2λ⁶-thia-1-aza-spiro[4.5]deca-6,9-dien-8-one
• 英文别名: 1-methoxy-2,2-dioxo-2λ6-thia-1-aza-spiro[4,5]deca-6,9-dien-8-one；N-methoxy-2,2-dioxo-21(6)-thia-1-azaspiro[4.5]deca-6,9-dien-8-one；2-Thia-1-azaspiro[4.5]deca-6,9-dien-8-one, 1-methoxy-, 2,2-dioxide；1-methoxy-2,2-dioxo-2λ6-thia-1-azaspiro[4.5]deca-6,9-dien-8-one
• CAS: 593288-18-7
• 化学式: C₉H₁₁NO₄S
• 分子量: 229.257
• InChiKey: OOOTXRJVROEOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-methoxy-2-(4'-methoxyphenyl)ethanesulfonamide 在 hydroxy(3-(trifluoromethyl)phenyl)- λ³-iodaneyl 4-methylbenzenesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以66%的产率得到N-methoxy-2,2-dioxo-2λ⁶-thia-1-aza-spiro[4.5]deca-6,9-dien-8-one
  参考文献：
  名称：

  Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes

  摘要：

  对β位含芳环的磺酰胺与各种有机超价碘化合物进行环化反应，形成相应的2,1-苯并噻嗪衍生物。其中，环化反应通过离子途径有效地与[羟基（对甲苯磺酰氧基）碘]芳烃进行。对β位含4-甲氧基苯基的磺酰胺进行同样的处理，可生成螺环化合物。

  DOI：

  10.1039/b301330h

文献信息

• 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.