(E)-butyl 3-[N-(2-pyridylsulfonyl)indolin-7-yl]acrylate | 1423075-26-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-butyl 3-[N-(2-pyridylsulfonyl)indolin-7-yl]acrylate
• 英文别名: (E)-butyl 3-(1-(pyridin-2-ylsulfonyl)indolin-7-yl)acrylate；butyl (E)-3-(1-pyridin-2-ylsulfonyl-2,3-dihydroindol-7-yl)prop-2-enoate
• CAS: 1423075-26-6
• 化学式: C₂₀H₂₂N₂O₄S
• 分子量: 386.472
• InChiKey: PKMGAVWGUKYRBX-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-butyl 3-[N-(2-pyridylsulfonyl)indolin-7-yl]acrylate 在 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：

  吡啶-2-磺酰氯 在 palladium diacetate 、 sodium hydride 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (E)-butyl 3-[N-(2-pyridylsulfonyl)indolin-7-yl]acrylate
  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

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.