Pyridyl-2-neopentylsulfonate | 111480-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Pyridyl-2-neopentylsulfonate
• 英文别名: neopentyl pyridine-2-sulfonate；2,2-Dimethylpropyl pyridine-2-sulfonate
• CAS: 111480-81-0
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: JDUNMDKUFNMBJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  47 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  336.9±15.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴吡啶 、 Pyridyl-2-neopentylsulfonate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以92 %的产率得到2,2'-联吡啶
  参考文献：
  名称：

  Divergent reactivities of 2-pyridyl sulfonate esters. Exceptionally mild access to alkyl bromides and 2-substituted pyridines

  摘要：

  A series of 2- and 3-pyridyl sulfonate and tosylate esters of primary and secondary alcohols were synthesized and evaluated in the bromination reaction with MgBr2·Et2O. The greater coordinating ability of the 2-pyridyl sulfonate esters accounted for its observed superior reactivity and selectivity. Reaction of neopentyl and phenyl 2-pyridyl sulfonates with a variety of aryl and heteroaryl Li reagents led to 2-substituted pyridines at temperatures as low as −78 °C via an SNAr process. Mechanistic considerations are discussed.

  DOI：

  10.1139/cjc-2020-0510
• 作为产物：
  描述：

  新戊醇 、 吡啶-2-磺酰氯 在 三甲胺盐酸盐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85 %的产率得到Pyridyl-2-neopentylsulfonate
  参考文献：
  名称：

  Divergent reactivities of 2-pyridyl sulfonate esters. Exceptionally mild access to alkyl bromides and 2-substituted pyridines

  摘要：

  A series of 2- and 3-pyridyl sulfonate and tosylate esters of primary and secondary alcohols were synthesized and evaluated in the bromination reaction with MgBr2·Et2O. The greater coordinating ability of the 2-pyridyl sulfonate esters accounted for its observed superior reactivity and selectivity. Reaction of neopentyl and phenyl 2-pyridyl sulfonates with a variety of aryl and heteroaryl Li reagents led to 2-substituted pyridines at temperatures as low as −78 °C via an SNAr process. Mechanistic considerations are discussed.

  DOI：

  10.1139/cjc-2020-0510

文献信息

• A Novel Regiospecific Synthesis of 2-Substituted Pyridines
  作者：Stephen Hanessian、Masahiro Kagotani

  DOI：10.1055/s-1987-27967

  日期：——

  A simple method is described for the mild and efficient conversion of pyridyl-2-alkylsulfonates into 2-alkyl and 2-arylpyridities.

  描述了一种简单的方法，可温和有效地将吡啶基-2-烷基磺酸盐转化为2-烷基和2-芳基吡啶基。
• HANESSIAN S.; KAGOTANI MASAHIRO, SYNTHESIS,(1987) N 4, 409-411
  作者：HANESSIAN S.、 KAGOTANI MASAHIRO

  DOI：——

  日期：——