N-(2-iodobenzyl)methanesulfonamide | 791065-79-7

• 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-(2-iodobenzyl)methanesulfonamide
• 英文别名: Methanesulfonamide, N-[(2-iodophenyl)methyl]-；N-[(2-iodophenyl)methyl]methanesulfonamide
• CAS: 791065-79-7
• 化学式: C₈H₁₀INO₂S
• 分子量: 311.143
• InChiKey: UIAGPHQCPUHBER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-iodobenzyl)methanesulfonamide 在 palladium diacetate cesium fluoride 、 三环己基膦 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 5,6-dihydro-5-(methylsulfonyl)phenanthridine
  参考文献：
  名称：

  Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization

  摘要：

  An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.071
• 作为产物：
  描述：

  2-碘代甲苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 三乙胺 、 三苯基膦 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 60.0h， 生成 N-(2-iodobenzyl)methanesulfonamide
  参考文献：
  名称：

  用于合成 Azaoxa- 和 Diazaspirocycles 的银催化串联环化**

  摘要：

  1-Azaspirocycles 代表在许多批准的药物和天然产品中发现的重要结构基序。因此，研究人员试图开发有效的催化系统来访问该支架。这项工作报道了在银催化下，从带有两个悬垂的氮基和氧基亲核试剂的炔烃中合成各种氮杂氧杂环和二氮杂螺环。

  DOI：

  10.1002/ejoc.202201404

文献信息

• Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling of <i>o</i>-Iodoanilines and <i>o</i>-Iodophenols with Silylaryl Triflates
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/ol048564l

  日期：2004.10.1

  An efficient route to synthesize a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. This chemistry tolerates a variety of functional groups.
• Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1016/j.tet.2006.10.071

  日期：2007.1

  An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps. (c) 2006 Elsevier Ltd. All rights reserved.
• Silver‐Catalyzed Tandem Cyclization for Syntheses of Azaoxa‐ and Diazaspirocycles**
  作者：Momoka Shimaoka、Masahiro Sai

  DOI：10.1002/ejoc.202201404

  日期：2023.3

  Therefore, researchers have tried to develop efficient catalytic systems to access this scaffold. This work reports the synthesis of various azaoxa- and diazaspirocycles from alkynes bearing two pendant nitrogen- and oxygen-based nucleophiles under silver catalysis.

  1-Azaspirocycles 代表在许多批准的药物和天然产品中发现的重要结构基序。因此，研究人员试图开发有效的催化系统来访问该支架。这项工作报道了在银催化下，从带有两个悬垂的氮基和氧基亲核试剂的炔烃中合成各种氮杂氧杂环和二氮杂螺环。