N-methoxy-2-(phenyl)ethanesulfonamide | 593288-00-7

• 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: N-methoxy-2-(phenyl)ethanesulfonamide
• 英文别名: N-Methoxy-2-phenylethane-1-sulfonamide；N-methoxy-2-phenylethanesulfonamide
• CAS: 593288-00-7
• 化学式: C₉H₁₃NO₃S
• 分子量: 215.273
• InChiKey: MLDGVDCNVAVPBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  N-methoxy-2-(phenyl)ethanesulfonamide 在 samarium diiodide 、 羟基甲苯磺酰碘苯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.33h， 生成 3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide
  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
• 作为产物：
  描述：

  2-苯基-乙烷磺酰氯 、 N-甲基羟胺盐酸盐 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 以98 %的产率得到N-methoxy-2-(phenyl)ethanesulfonamide
  参考文献：
  名称：

  [EN] A1H-BENZO[C][1,2]THIADIAZINE-2,2-DIOXIDES BEARING HETEROCYCLIC LINKERS AS SELECTIVE HISTONE DEACETYLASE 6 INHIBITORS
  [FR] A1H-BENZO[C][1,2]THIADIAZINE-2,2-DIOXIDES PORTANT DES LIEURS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS SÉLECTIFS DE L'HISTONE DÉSACÉTYLASE 6

  摘要：

  Histone deacetylases inhibitors (HDACbls) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC6 provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease including peripheral neuropathies such as Charcot Marie Tooth disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.

  公开号：

  WO2023154758A1

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
• 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。
• Metal-Free C–H Sulfamidation of 1,4-Naphthoquinone in Water
  作者：Pallaba Ganjan Dalai、Swayamprava Swain、Soumya Mohapatra、Niranjan Panda

  DOI：10.1021/acs.joc.3c01409

  日期：2023.10.6

  Direct sulfamidation of 1,4-naphthoquinones using N-methoxy sulfonamides under metal-free conditions in water was developed. Base-mediated nucleophilic addition of N-methoxy sulfonamides, followed by N–O bond cleavage allowed the formation of enesulfonamides. Further, the synthesis of pyrrolonaphthoquinones proved the practicability of the current approach.

  开发了在水中无金属条件下使用N-甲氧基磺酰胺直接磺酰胺化 1,4-萘醌的方法。N-甲氧基磺酰胺的碱介导亲核加成，随后 N-O 键断裂，形成烯磺酰胺。此外，吡咯并萘醌的合成证明了该方法的实用性。
• 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.