2-methylbenzo[d]thiazol-5-yl methanesulfonate | 1011481-52-9

• 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-methylbenzo[d]thiazol-5-yl methanesulfonate
• 英文别名: 2-methyl-1,3-benzothiazol-5-yl methanesulfonate；2-methylbenzo[d]thiazol-5-yl mesylate；(2-Methyl-1,3-benzothiazol-5-yl) methanesulfonate；(2-methyl-1,3-benzothiazol-5-yl) methanesulfonate
• CAS: 1011481-52-9
• 化学式: C₉H₉NO₃S₂
• 分子量: 243.307
• InChiKey: NDMJWJHYCFIWKV-UHFFFAOYSA-N

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-methylbenzo[d]thiazol-5-yl methanesulfonate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 sodium carbonate 、 乙二胺 作用下， 以 1,4-二氧六环 、 丙醇 、 水 为溶剂， 反应 48.0h， 生成 (2-Methylbenzo[d]thiazol-5-yl)methanamine
  参考文献：
  名称：

  One-Pot Primary Aminomethylation of Aryl and Heteroaryl Halides with Sodium Phthalimidomethyltrifluoroborate

  摘要：

  A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.

  DOI：

  10.1021/ol301037s
• 作为产物：
  描述：

  2-甲基-5-苯并噻唑 、 甲基磺酰氯 在 三甲胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以72%的产率得到2-methylbenzo[d]thiazol-5-yl methanesulfonate
  参考文献：
  名称：

  钯催化的甲苯磺酸芳基酯和甲磺酸酯的羰基化

  摘要：

  已经使用衍生自 Pd(OAc)2 和庞大的双齿 dcpp 配体的催化剂系统开发了钯催化的甲苯磺酸芳基酯和甲磺酸酯羰基化形成酯的通用方案。该系统在温和的条件下运行：大气 CO 压力和 80-110 摄氏度的温度。 广泛的底物范围已被证明允许富电子、缺电子和杂环甲苯磺酸酯和甲磺酸酯羰基化，反应显示出广泛的官能团宽容。

  DOI：

  10.1021/ja711449e

文献信息

• An efficient palladium–benzimidazolyl phosphine complex for the Suzuki–Miyaura coupling of aryl mesylates: facile ligand synthesis and metal complex characterization
  作者：Kin Ho Chung、Chau Ming So、Shun Man Wong、Chi Him Luk、Zhongyuan Zhou、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1039/c2cc15972d

  日期：——

  A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl mesylates is still observed. This represents the lowest catalyst

  已经开发出一种新型的易于获得的半不稳定的苯并咪唑基膦配体。配体骨架由可商购的和廉价的邻苯二胺和2-溴苯甲酸制备。在催化剂负载量低至0.5mol％钯的情况下，仍观察到对甲磺酸甲磺酸酯的Suzuki-Miyaura偶联的优异催化活性。通常，这代表了迄今为止该反应所达到的最低催化剂负载量。X射线晶体学表明，新的配体L2以Kappa（2）-P，N的方式与Pd配合。
• Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates
  作者：Wai Chung Fu、Chau Ming So、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.5b03104

  日期：2015.12.4

  The first general palladium catalyst for the phosphorylation of aryl mesylates and tosylates is reported. The newly developed system exhibits excellent functional group compatibility. For instance, free amino, keto, ester, and amido groups, as well as heterocycles, remain intact during the course of reaction. The mesylated derivatives of biologically active compounds such as 17β-estradiol and 6-hydroxyflavone

  据报道，第一种用于芳基甲磺酸酯和甲苯磺酸酯磷酸化的通用钯催化剂。新开发的系统具有出色的功能组兼容性。例如，游离氨基，酮，酯和酰胺基以及杂环在反应过程中保持完整。还显示了生物活性化合物（如17β-雌二醇和6-羟基黄酮）的甲磺酸化衍生物是适用的底物。描述了一种一锅磷酸化-氨基化序列，可轻松合成潜在的药效基团。
• Palladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis
  作者：Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201100361

  日期：2011.6.14

  Top of the one‐pots! The first palladium‐catalyzed borylation of aryl tosylates and mesylates is described. The reaction conditions are mild and provide excellent functional‐group compatibility (e.g., R=CN, CHO, COOMe, C(O)R, NH2, or NH‐indole; see scheme). Pd/MeO‐CM‐phos allows one‐pot sequential reactions in the preparation of unsymmetrical biaryls.

  一锅之巅！描述了芳基甲苯磺酸盐和甲磺酸盐的第一个钯催化的硼化反应。反应条件温和，并具有出色的官能团相容性（例如，R = CN，CHO，COOMe，C（O）R，NH 2或NH-吲哚；请参见方案）。Pd / MeO-CM-phos可在不对称联芳烃的制备中进行一锅法依次反应。
• Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates
  作者：Pui Ying Choy、Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201001269

  日期：2010.9.3

  Up to speed: The first general and mild protocol for the Sonogashira coupling of aryl mesylates is presented (see scheme). The coupling intermediate also provides facile access to 2‐substituted isoquinolines.

  加快速度：提出了甲磺酸甲磺酸酯的Sonogashira偶联的第一个一般性和温和的方案（请参阅方案）。偶联中间体还提供了2取代异喹啉的便捷通道。
• A General Palladium Catalyst System for Suzuki−Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates
  作者：Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1021/jo100846t

  日期：2010.8.6

  The first general examples of palladium-catalyzed Suzuki-type cross-coupling of aryl and heteroaryl mesylates with potassium aryl and heteroaryltrifluoroborates are presented. In addition to biaryl couplings, the cross-coupling reactions of aryl mesylates with alkyl and vinyltrifluoroborate salts have also been successfully accomplished.

  给出了芳基和杂芳基甲磺酸酯与芳基钾和杂芳基三氟硼酸钾的钯催化的Suzuki型交叉偶联的第一个一般实例。除了联芳基偶合以外，还成功地完成了甲磺酸甲基芳基酯与烷基和乙烯基三氟硼酸酯盐的交叉偶联反应。