2-methyl-benzothiazol-6-yl mesylate | 1092513-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-methyl-benzothiazol-6-yl mesylate
• 英文别名: 2-methyl-6-benzothiazolyl mesylate；6-methanesulfonyloxy-2-methylbenzothiazole；(2-Methyl-1,3-benzothiazol-6-yl) methanesulfonate
• CAS: 1092513-19-3
• 化学式: C₉H₉NO₃S₂
• 分子量: 243.307
• InChiKey: UWQHJCUHFHUJMR-UHFFFAOYSA-N

物化性质

• 熔点：
  119.5-120.8 °C
• 沸点：
  410.4±27.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-benzothiazol-6-yl mesylate 、 苯基三甲氧基硅烷 在 2-[2-(二环己基膦基)苯基]-N-甲基吲哚 、 四丁基氟化铵 、 palladium diacetate 、 溶剂黄146 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以68%的产率得到2-甲基-6-苯基苯并噻唑
  参考文献：
  名称：

  Palladium−Indolylphosphine-Catalyzed Hiyama Cross-Coupling of Aryl Mesylates

  摘要：

  Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)(2) and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.

  DOI：

  10.1021/ol802493z
• 作为产物：
  描述：

  2-甲基-6-羟基苯并噻唑 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以38%的产率得到2-methyl-benzothiazol-6-yl mesylate
  参考文献：
  名称：

  Palladium−Indolylphosphine-Catalyzed Hiyama Cross-Coupling of Aryl Mesylates

  摘要：

  Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)(2) and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.

  DOI：

  10.1021/ol802493z

文献信息

• Palladium-catalyzed Buchwald-Hartwig Amination and Suzuki-Miyaura Cross-coupling Reaction of Aryl Mesylates
  作者：Shun Wong

  DOI：10.15227/orgsyn.092.0195

  日期：——
• A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
  作者：Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.200803193

  日期：2008.10.6
• Ligands for transition-metals and methods of use
  申请人：Kwong Fuk Yee

  公开号：US20090326243A1

  公开（公告）日：2009-12-31

  The present invention relates to indolyl phosphine ligands, and methods of making such ligands utilizing phenyl hydrazines and aryl ketones as the starting material. The present invention further includes uses of the ligands in the synthesis of pharmaceuticals, materials, and agriculture.
• US8212056B2
  申请人：——

  公开号：US8212056B2

  公开（公告）日：2012-07-03
• Palladium−Indolylphosphine-Catalyzed Hiyama Cross-Coupling of Aryl Mesylates
  作者：Chau Ming So、Hang Wai Lee、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1021/ol802493z

  日期：2009.1.15

  Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)(2) and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.