isoquinolin-5-yl methanesulfonate | 1186126-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: isoquinolin-5-yl methanesulfonate
• 英文别名: isoquinolin-5-ylmethanesulfonate
• CAS: 1186126-52-2
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: GRSWHSGNJFGRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.26
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  isoquinolin-5-yl methanesulfonate 、 (吡啶鎓-1-基甲基)三氟硼酸盐 在 potassium phosphate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 、 盐酸 作用下， 以 水 、 叔丁醇 、 乙醚 为溶剂， 反应 18.0h， 以98%的产率得到5-(piperidin-1-ylmethyl)isoquinoline hydrochloride
  参考文献：
  名称：

  Cross-Coupling of Mesylated Phenol Derivatives with Potassium Ammonio- and Amidomethyltrifluoroborates

  摘要：

  A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp(2)-Csp(3) Suzuki-Miyaura cross-coupling with potassium ammonio- and amidomethyltrifluoroborates to afford the corresponding products in high yields.

  DOI：

  10.1021/ol200128y
• 作为产物：
  描述：

  甲基磺酰氯 、 5-羟基异喹啉 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到isoquinolin-5-yl methanesulfonate
  参考文献：
  名称：

  Nickel-Catalyzed C−O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates

  摘要：

  A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.

  DOI：

  10.1021/ol101592r

文献信息

• Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates
  作者：Nathaniel H. Park、Georgiy Teverovskiy、Stephen L. Buchwald

  DOI：10.1021/ol403209k

  日期：2014.1.3

  A new air-stable nickel precatalyst for C–N cross-coupling is reported. The developed catalyst system displays a greatly improved substrate scope for C–N bond formation to include both a wide range of aryl and heteroaryl electrophiles and aryl, heteroaryl, and alkylamines. The catalyst system is also compatible with a weak base, allowing the amination of substrates containing base-sensitive functional

  报道了一种用于 C-N 交叉偶联的新型空气稳定镍预催化剂。开发的催化剂体系显示出极大改进的 C-N 键形成底物范围，包括各种芳基和杂芳基亲电试剂以及芳基、杂芳基和烷基胺。该催化剂体系还与弱碱相容，允许含碱敏感官能团的底物胺化。
• Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents
  作者：Stephen D. Ramgren、Liana Hie、Yuxuan Ye、Neil K. Garg

  DOI：10.1021/ol401727y

  日期：2013.8.2

  The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)(2), and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.
• 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.
• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Alkoxymethyltrifluoroborates
  作者：Gary A. Molander、Floriane Beaumard

  DOI：10.1021/ol201469r

  日期：2011.8.5

  Cross-coupling of mesylated phenol derivatives with various potassium alkoxymethyltrifluoroborates has been achieved. The corresponding aryl and heteroaryl alkoxymethyl compounds have been obtained with equal facility with both electron-rich and electron-poor substituents on the activated alcohol.
• Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates
  作者：Gary A. Molander、Inji Shin

  DOI：10.1021/ol301221p

  日期：2012.6.15

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.