2-butyl-1-tosylpyrrolidine | 2066-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-butyl-1-tosylpyrrolidine
• 英文别名: 2-Butyl-1-(4-methylphenyl)sulfonylpyrrolidine
• CAS: 2066-30-0
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: XEOSZLRNUREVPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲基-N-辛基苯磺酰胺 在 copper(l) iodide 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以64%的产率得到2-butyl-1-tosylpyrrolidine
  参考文献：
  名称：

  铜催化的远程（δ）C（sp 3）–H键胺化：构建吡咯烷衍生物的实用策略

  摘要：

  我们报告了铜催化的远程C（sp 3）–H键胺化反应，该反应将无环胺转化为吡咯烷。该反应选择性地发生在对胺官能度的碳δ处。伯，仲和叔碳氢键均适用于存在廉价和市售铜催化剂的情况下的胺化反应。

  DOI：

  10.1039/c7cc02624b

文献信息

• Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu, Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2368 - 2372
  作者：Shono, Tatsuya、Matsumura, Yoshihiro、Katoh, Susumu、Takeuchi, Kei、Sasaki, Katsushi、Kamada, Tohru、Shimizu, Rie

  DOI：——

  日期：——
• Visible-Light-Promoted Remote C(sp³)–H Amidation and Chlorination
  作者：Qixue Qin、Shouyun Yu

  DOI：10.1021/acs.orglett.5b00582

  日期：2015.4.17

  A visible-light-promoted C(sp(3))-H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp(3))-H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp3)H functionalization of complex and biologically important (-)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.
• δ and α SP³ C−H Bond Oxidation of Sulfonamides with PhI(OAc)₂/I₂ under Metal-Free Conditions
  作者：Renhua Fan、Dongming Pu、Fengqi Wen、Jie Wu

  DOI：10.1021/jo7016982

  日期：2007.11.1

  [GRAPHICS]An efficient delta and alpha sp(3) C-H bond oxidation of sulfonamides with PhI(OAc)(2)/I-2 under metal-free conditions has been reported. The reaction provides a useful route to pyrrolidines, N-sulfonylimines, and various sulfonamide derivatives. The potential of this reaction system can be evaluated by its mild condition and simple process.
• Copper-catalyzed remote (δ) C(sp³)–H bond amination: a practical strategy to construct pyrrolidine derivatives
  作者：Dongmei Meng、Yongzhen Tang、Junfa Wei、Xianying Shi、Mingyu Yang

  DOI：10.1039/c7cc02624b

  日期：——

  We report a copper-catalyzed remote C(sp3)–H bond amination reaction that converts acyclic amines to pyrrolidines. This reaction occurs selectively at the carbon δ to the amine functionality. Primary, secondary and tertiary C–H bonds are all suitable for the amination reactions in the presence of an inexpensive and commercially available copper catalyst.

  我们报告了铜催化的远程C（sp 3）–H键胺化反应，该反应将无环胺转化为吡咯烷。该反应选择性地发生在对胺官能度的碳δ处。伯，仲和叔碳氢键均适用于存在廉价和市售铜催化剂的情况下的胺化反应。