2-fluoro-7-methoxy-9H-carbazole | 344780-33-2

• 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: 2-fluoro-7-methoxy-9H-carbazole
• 英文别名: 7-fluoro-2-methoxy-9H-carbazole
• CAS: 344780-33-2
• 化学式: C₁₃H₁₀FNO
• 分子量: 215.227
• InChiKey: YMPRWZUFGSHJBU-UHFFFAOYSA-N

物化性质

• 沸点：
  395.4±22.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-fluoro-7-methoxy-9H-carbazole 在 C₂₂H₃₄NO₅V 、 氧气 、 三溴化硼 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 生成 7,7’-difluoro-9,9’-dimethyl-[1,3’-bicarbazole]-2,2’-diol
  参考文献：
  名称：

  Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

  摘要：

  The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.

  DOI：

  10.1021/ol503521b
• 作为产物：
  描述：

  2-溴-5-氟硝基苯 在 铜 、 亚磷酸三乙酯 作用下， 生成 2-fluoro-7-methoxy-9H-carbazole
  参考文献：
  名称：

  Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

  摘要：

  The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.

  DOI：

  10.1021/ol503521b

文献信息

• One-pot synthesis of carbazoles via tandem C–C cross-coupling and reductive amination
  作者：Deuk-Young Goo、Sang Kook Woo

  DOI：10.1039/c5ob01952d

  日期：——

  We have developed a highly efficient synthetic route to carbazoles that employs sequential C–C/C–N bond formation via Suzuki cross-coupling and Cadogan cyclization. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products.

  我们已经开发出一种高效的合成路线，用于合成咔唑，该路线利用了顺序C–C/C–N键形成，通过Suzuki交叉偶联和Cadogan环化。这种方法适用于电子中性、富电子或缺电子底物。通过这种方法的简洁合成，我们展示了四种天然产物的合成效用。
• Novel substituted tricyclic compounds
  申请人：——

  公开号：US20030040538A1

  公开（公告）日：2003-02-27

  Compounds of the general formula (I) are useful in the treatment and prevention of &bgr;3-related diseases including diabetes, obesity and hyperlipidemia wherein R 1 is hydrogen, halogen, or hydroxyl; R 2 is C 1-4 alkyl or benzyl; R 3 is OR, halogen, trifluoromethyl, C 1-8 alkyl, lower acyl, NR 4 R 4′ , nitro, or cyano; R is hydrogen, C 1-8 alkyl, benzyl group, or optionally substituted lower acyl; R 4 and R 4′ are each independently hydrogen, C 1-4 alkyl, lower acyl, benzyl, or SO 2 R 5 ; R 5 is C 1-4 alkyl or benzyl; W is oxygen, a secondary nitrogen atom (NH), or sulfur; and * represents an asymmetric carbon atom. 1

  通式（I）的化合物在治疗和预防与β3相关的疾病，包括糖尿病、肥胖症和高脂血症方面具有用处，其中R1是氢、卤素或羟基；R2是C1-4烷基或苄基；R3是OR、卤素、三氟甲基、C1-8烷基、较低酰基、NR4R4'、硝基或氰基；R是氢、C1-8烷基、苄基或可选取代的较低酰基；R4和R4'各自独立地为氢、C1-4烷基、较低酰基、苄基或SO2R5；R5是C1-4烷基或苄基；W是氧、次级氮原子（NH）或硫；*代表不对称碳原子。
• Pd(II)/Lewis Acid Catalyzed Intramolecular Oxidative C−H Amination to Construct Carbazoles with Dioxygen
  作者：Hongwu Jiang、Kaiwen Li、Shuangfeng Dong、Zhuqi Chen、Guochuan Yin

  DOI：10.1002/ejoc.202300598

  日期：2023.9.14

  Transition‐metal‐catalyzed oxidative C−H amination reactions are among the most attractive topics in organic synthesis to construct nitrogen‐containing motifs. The challenge is that most of these reactions employed stoichiometric oxidants to achieve satisfied catalytic efficiencies. Herein, we report a Pd(II)/LA‐catalyzed (LA: Lewis acid) oxidative C−H amination reaction of 2‐acetaminobiphenyls to construct carbazoles by using dioxygen balloon as the sole oxidant source, and the presence of LA sharply improved the catalytic efficiency of Pd(OAc)₂. Remarkably, in certain cases, the deacetylation of the annulation product happened under standard conditions to afford free carbazoles as the final product. The H/D exchange studies confirmed the reversibility of C−H activation and also disclosed multiple C−H activation sites by using −NAc and −NTs as the directing groups. In addition, the palladacycle compound was identified through ¹H NMR characterizations and proved to be the intermediate prior to the carbazole formation.

  摘要 过渡金属催化的氧化 C-H amination 反应是有机合成中构建含氮基团最有吸引力的课题之一。面临的挑战是，这些反应中的大多数都需要使用一定比例的氧化剂才能达到满意的催化效率。在此，我们报告了一种 Pd（II）/LA 催化（LA：路易斯酸）的 2-acetaminobiphenyls 氧化 C-H amination 反应，该反应以二氧气球作为唯一的氧化剂源来构建咔唑，LA 的存在极大地提高了 Pd（OAc）2 的催化效率。值得注意的是，在某些情况下，环化产物会在标准条件下发生脱乙酰化反应，从而得到游离的咔唑作为最终产物。H/D交换研究证实了C-H活化的可逆性，并通过使用-NAc和-NTs作为引导基团，发现了多个C-H活化位点。此外，通过 1H NMR 表征确定了帕拉代环化合物，并证明它是咔唑形成之前的中间体。
• NOVEL SUBSTITUTED TRICYCLIC COMPOUNDS
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP1238973A1

  公开（公告）日：2002-09-11

  Compounds of the general formula (I) are useful in the treatment and prevention of β3-related diseases including diabetes, obesity and hyperlipidemia wherein R1 is hydrogen, halogen, or hydroxyl; R2 is lower alkyl or benzyl; R3 is OR, halogen, trifluoromethyl, lower alkyl, lower acyl, NR4R4', nitro, or cyano; R is hydrogen, lower alkyl, benzyl group, or optionally substituted lower acyl; R4 and R4' are each independently hydrogen, lower alkyl, lower acyl, benzyl, or SO2R5; R5 is lower alkyl or benzyl; W is oxygen, a secondary nitrogen atom (NH), or sulfur; and * represents an asymmetric carbon atom.

  通式（I）化合物可用于治疗和预防与β3 有关的疾病，包括糖尿病、肥胖症和高脂血症 其中 R1 是氢、卤素或羟基；R2 是低级烷基或苄基；R3 是 OR、卤素、三氟甲基、低级烷基、低级酰基、NR4R4'、硝基或氰基；R 是氢、低级烷基、苄基或任选取代的低级酰基；R4 和 R4'各自独立地是氢、低级烷基、低级酰基、苄基或 SO2R5；R5 是低级烷基或苄基；W 是氧、仲氮原子 (NH) 或硫；以及 * 代表不对称碳原子。
• Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles
  作者：Lei Liu、Patrick J. Carroll、Marisa C. Kozlowski

  DOI：10.1021/ol503521b

  日期：2015.2.6

  The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.