(E,E)-dibutyl 3,3'-(9H-carbazole-1,8-diyl)diacrylate | 1423075-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E,E)-dibutyl 3,3'-(9H-carbazole-1,8-diyl)diacrylate
• CAS: 1423075-27-7
• 化学式: C₂₆H₂₉NO₄
• 分子量: 419.521
• InChiKey: WPPJOIRSEOXCTN-WXUKJITCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (E,E)-dibutyl 3,3'-[N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]diacrylate 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到(E,E)-dibutyl 3,3'-(9H-carbazole-1,8-diyl)diacrylate
  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

• Ligand‐Dependant Selective Synthesis of Mono‐ and Dialkenylcarbazoles through Rhodium(III)‐Catalyzed C−H Alkenylation
  作者：Rikuto Tanaka、Shiho Ochiai、Asumi Sakai、Yoshinosuke Usuki、Bubwoong Kang、Tetsuro Shinada、Tetsuya Satoh

  DOI：10.1002/asia.202201210

  日期：2023.2.14

  Selective mono- and dialkenylation of N-acetylcarbazoles was achieved by using Cp*Rh(III)- and CpERh(III)-catalysts, respectively. Unexpectedly, the dialkenylation was accompanied by the removal of acetyl directing group to produce 1,8-dialkenyl-N-H-carbazoles.

  N-乙酰咔唑的选择性单烯基化和二烯基化分别通过使用 Cp*Rh(III)- 和 Cp E Rh(III)- 催化剂实现。出乎意料的是，二烯基化伴随着乙酰基导向基团的去除，产生 1,8-二烯基-N -H-咔唑。