3-cholestanyl 2-pyridylsulfonate | 123468-18-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-cholestanyl 2-pyridylsulfonate
• CAS: 123468-18-8
• 化学式: C₃₂H₅₁NO₃S
• 分子量: 529.828
• InChiKey: KJTITDVKKBWIMN-ZVZGDOHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  3-cholestanyl 2-pyridylsulfonate 在 magnesium bromide ethyl etherate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以77 %的产率得到3α-bromo-5α-cholestane
  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：

  (3S,5S,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl pyridine-3-sulfonate 在 三甲胺盐酸盐 、 magnesium bromide ethyl etherate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-cholestanyl 2-pyridylsulfonate
  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

• Design and Reactivity of Organic Functional Groups — 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformations into HAlides and Olefins
  作者：Stephen Hanessian、Masahiro Kagotani、Kossi Komaglou

  DOI：10.3987/com-88-s134

  日期：——