2-[4-(chloromethyl)phenyl]-N-methoxyethanesulfonamide | 1031684-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-(chloromethyl)phenyl]-N-methoxyethanesulfonamide
• CAS: 1031684-26-0
• 化学式: C₁₀H₁₄ClNO₃S
• 分子量: 263.745
• InChiKey: ZSFSBEVVDRBXPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(chloromethyl)phenyl]-N-methoxyethanesulfonamide 在 间氯过氧苯甲酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 6.0h， 以65%的产率得到7-(chloromethyl)-1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide
  参考文献：
  名称：

  聚合物负载的碘代苯的新型制备及其作为间氯过苯甲酸可循环使用的试剂的合成效用

  摘要：

  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

  DOI：

  10.1055/s-0029-1218795

文献信息

• Iodobenzene-Catalyzed Preparation of 3,4-Dihydro-1<i>H</i>-2,1-benzothiazine 2,2-Dioxides from 2-Aryl-<i>N</i>-methoxyethanesulfonamides with <i>m</i>-Chloro­peroxybenzoic Acid
  作者：Hideo Togo、Atsushi Moroda

  DOI：10.1055/s-2008-1042945

  日期：2008.4

  Iodobenzene-catalyzed cyclization of 2-aryl-N-meth­oxyethanesulfonamides with m-chloroperoxybenzoic acid results in the corresponding 1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides in moderate to good yields. In this reaction, reactive hypervalent iodine [(hydroxy)(tosyloxy)iodo]benzene, formed in situ, reacts with the 2-aryl-N-methoxyethanesulfonamides in an electrophilic manner at the aromatic ring to give the corresponding 1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides.

  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。
• 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.