methyl 3-((N,N-dimethylsulfamoyl)oxy)benzoate | 338396-38-6

• 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: methyl 3-((N,N-dimethylsulfamoyl)oxy)benzoate
• 英文别名: Methyl 3-{[(dimethylamino)sulfonyl]oxy}benzenecarboxylate；methyl 3-(dimethylsulfamoyloxy)benzoate
• CAS: 338396-38-6
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: OZSHONVWUXQGGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-((N,N-dimethylsulfamoyl)oxy)benzoate 、 5,5-二甲基-2-苯基-1,3,2-二氧硼杂 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到3-苯基苯甲酸甲酯
  参考文献：
  名称：

  Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature

  摘要：

  Reaction conditions for the Ni(COD)(2)/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)(2)/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.

  DOI：

  10.1021/jo202037x
• 作为产物：
  描述：

  3-羟基苯甲酸甲酯 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.17h， 以75%的产率得到methyl 3-((N,N-dimethylsulfamoyl)oxy)benzoate
  参考文献：
  名称：

  Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature

  摘要：

  Reaction conditions for the Ni(COD)(2)/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)(2)/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.

  DOI：

  10.1021/jo202037x

文献信息

• <i>trans</i>-Chloro(1-Naphthyl)bis(triphenylphosphine)nickel(II)/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates at Room Temperature
  作者：Pawaret Leowanawat、Na Zhang、Mehtap Safi、David J. Hoffman、Miriam C. Fryberger、Aiswaria George、Virgil Percec

  DOI：10.1021/jo3001194

  日期：2012.3.16

  been successfully applied as catalyst for the Suzuki–Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench

  反式-氯（1-萘基）双（三苯基膦）镍（II）配合物/ PCy 3体系已成功用作Suzuki-Miyaura的芳烃和杂芳基新戊二醇硼酸酯与芳基和杂芳基甲磺酸酯和氨基磺酸酯的Suzuki-Miyaura交叉偶联室内温度。这种交叉偶联反应可耐受各种官能团，包括酮基，亚氨基，酯基，醚基和氰基。与镍催化的一锅两步新戊基糖基化反应一起使用，这种台式稳定且廉价的Ni（II）基催化剂可以用作Ni（COD）2 / PCy 3的替代品，从而提供廉价，坚固，方便地合成联芳基和杂联芳基化合物。
• Ni(COD)₂/PCy₃ Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature
  作者：Pawaret Leowanawat、Na Zhang、Ana-Maria Resmerita、Brad M. Rosen、Virgil Percec

  DOI：10.1021/jo202037x

  日期：2011.12.16

  Reaction conditions for the Ni(COD)(2)/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)(2)/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.