N-(2-pyridyl)sulfonyl indoline | 1026564-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(2-pyridyl)sulfonyl indoline
• 英文别名: 1-Pyridin-2-ylsulfonyl-2,3-dihydroindole
• CAS: 1026564-85-1
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: YLGUCTULPJIIKO-UHFFFAOYSA-N

物化性质

• 沸点：
  440.7±47.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-pyridyl)sulfonyl indoline 在 palladium diacetate 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 、 magnesium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 pyrrolo[3,2,1-ij]quinolin-4-one
  参考文献：
  名称：

  Pd^II-Catalyzed Di-o-olefination of Carbazoles Directed by the Protecting N-(2-Pyridyl)sulfonyl Group

  摘要：

  Despite the significance of carbazole in pharmacy and material science, examples of the direct C-H functionalization of this privileged unit are quite rare. The N-(2-pyridyl)sulfonyl group enables the Pd-II-catalyzed ortho-olefination of carbazoles and related systems, acting as both a directing and readily removable protecting group. This method features ample structural versatility, affording typically the double ortho-olefination products (at Cl and C8) in satisfactory yields and complete regiocontrol. The application of this procedure to related heterocyclic systems, such as indoline, is also described.

  DOI：

  10.1021/ol400206k
• 作为产物：
  描述：

  N-(2-phenylethyl)pyridine-2-sulfonamide 在 碘苯二乙酸 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以82%的产率得到N-(2-pyridyl)sulfonyl indoline
  参考文献：
  名称：

  Synthesis of Indolines via Pd(II)-Catalyzed Amination of C–H Bonds Using PhI(OAc)₂ as the Bystanding Oxidant

  摘要：

  The Pd(II)-catalyzed intramolecular C-H amination of 2-pyridinesulfonyl-protected phenethylamine derivatives has been achieved using Phl(OAc)(2) as a bystanding oxidant, providing access to a variety of substituted indoline derivatives in good yields. The use of the 2-pyridlnesulfonyl protecting group allows for facile deprotection following C-H functionalization.

  DOI：

  10.1021/ol401246u

文献信息

• Palladium-catalyzed C-7 alkenylation of indolines using molecular oxygen as the sole oxidant
  作者：Dong Yang、Shuai Mao、Ya-Ru Gao、Dong-Dong Guo、Shi-Huan Guo、Bin Li、Yong-Qiang Wang

  DOI：10.1039/c5ra02245b

  日期：——

  A general and efficient method for the intermolecular direct C-7-selective C–H alkenylation of indolines using palladium(II) as the catalyst and molecular oxygen as the sole oxidant has been developed. The reaction showed complete regio- and stereoselectivity. All products were E-isomers at the C-7 position, and no Z-isomers or other position substituted products could be detected. The approach also

  已经开发了一种通用有效的方法，以钯（II）为催化剂，分子氧为唯一氧化剂，使吲哚的分子间直接C-7-选择性CH链烯基化。反应显示出完全的区域选择性和立体选择性。所有产物在C-7位均为E-异构体，未检测到Z-异构体或其他位置取代的产物。该方法还提供了合成C-7烯基化吲哚的有效途径。
• Pd^II-Catalyzed Di-<i>o</i>-olefination of Carbazoles Directed by the Protecting <i>N</i>-(2-Pyridyl)sulfonyl Group
  作者：Beatriz Urones、Ramón Gómez Arrayás、Juan Carlos Carretero

  DOI：10.1021/ol400206k

  日期：2013.3.1

  Despite the significance of carbazole in pharmacy and material science, examples of the direct C-H functionalization of this privileged unit are quite rare. The N-(2-pyridyl)sulfonyl group enables the Pd-II-catalyzed ortho-olefination of carbazoles and related systems, acting as both a directing and readily removable protecting group. This method features ample structural versatility, affording typically the double ortho-olefination products (at Cl and C8) in satisfactory yields and complete regiocontrol. The application of this procedure to related heterocyclic systems, such as indoline, is also described.
• Synthesis of Indolines via Pd(II)-Catalyzed Amination of C–H Bonds Using PhI(OAc)₂ as the Bystanding Oxidant
  作者：Tian-Sheng Mei、Dasheng Leow、Han Xiao、Brian N. Laforteza、Jin-Quan Yu

  DOI：10.1021/ol401246u

  日期：2013.6.21

  The Pd(II)-catalyzed intramolecular C-H amination of 2-pyridinesulfonyl-protected phenethylamine derivatives has been achieved using Phl(OAc)(2) as a bystanding oxidant, providing access to a variety of substituted indoline derivatives in good yields. The use of the 2-pyridlnesulfonyl protecting group allows for facile deprotection following C-H functionalization.