9H-carbazole-3-carboxylic acid ethyl ester | 51035-14-4

• 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: 9H-carbazole-3-carboxylic acid ethyl ester
• 英文别名: 3-carbazolecarboxylic acid ethyl ester；ethyl 9H-carbazole-3-carboxylate；ethyl carbazole-3-carboxylate；3-(Ethoxycarbonyl)carbazole；3-carboxyethylcarbazole；carbazole-3-carboxylic acid ethyl ester
• CAS: 51035-14-4
• 化学式: C₁₅H₁₃NO₂
• mdl: MFCD03144111
• 分子量: 239.274
• InChiKey: NLLKBEGFXZYBFX-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  429.4±18.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9H-carbazole-3-carboxylic acid ethyl ester 在 盐酸 、 铜 、 potassium carbonate 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 9-(2-amino-phenyl)-carbazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  399.尝试制备旋光性叔氮化合物。第一部分：1：9-亚苯基咔唑及其衍生物的合成

  摘要：

  DOI：

  10.1039/jr9390001945
• 作为产物：
  描述：

  3,4-二氯苯甲酸 在 palladium diacetate potassium phosphate 、 硫酸 、 三环己基膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 30.0h， 生成 9H-carbazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Domino NH / CH键活化：使用二氯（杂）芳烃的钯催化合成杂环。

  摘要：

  DOI：

  10.1002/anie.200603833

文献信息

• Lewis Acid-Promoted Synthesis of Unsymmetrical and Highly Functionalized Carbazoles and Dibenzofurans from Biaryl Triazenes: Application for the Total Synthesis of Clausine C, Clausine R, and Clauraila A
  作者：Weijun Yang、Jun Zhou、Binjie Wang、Hongjun Ren

  DOI：10.1002/chem.201102802

  日期：2011.12.2

  A natural approach: A Lewis acid‐promoted nucleophilic aromatic substitution approach to the regioselective synthesis of highly substituted carbazoles and dibenzofurans has been developed. The annulation process is applied to the total synthesis of carbazole alkaloids clausine C, clausine R, and clauraila A (see scheme).

  一种自然方法：已开发出一种路易斯酸促进的亲核芳族取代方法，用于高度取代的咔唑和二苯并呋喃的区域选择性合成。环化工艺应用于咔唑生物碱克劳斯汀C，克劳斯汀R和克劳拉艾拉A的全合成（请参阅方案）。
• Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20160028027A1

  公开（公告）日：2016-01-28

  An object is to provide a novel organometallic complex. Another object is to provide an organometallic complex exhibiting green to blue phosphorescence. Another object is to provide an organometallic complex having deep HOMO and exhibiting green to blue phosphorescence. Another object is to provide a light-emitting element with high emission efficiency. Another object is to provide a light-emitting element exhibiting green to blue phosphorescence and having low drive voltage. To provide an organometallic complex which includes a 1,2,4-triazole skeleton and in which an N-carbazolyl group is bonded to the 3-position of the 1,2,4-triazole skeleton via a phenylene group, a phenyl group is bonded to the 4-position of the 1,2,4-triazole skeleton, the 2-position of the 1,2,4-triazole skeleton coordinates to iridium, and the phenylene group is bonded to the iridium. To provide a light-emitting element including the organometallic complex as an emission center.

  一个目的是提供一种新型的有机金属配合物。另一个目的是提供一种显示绿色到蓝色磷光的有机金属配合物。另一个目的是提供一种具有深层HOMO并能显示绿色到蓝色磷光的有机金属配合物。另一个目的是提供一种具有高发射效率的发光元件。另一个目的是提供一种显示绿色到蓝色磷光且驱动电压低的发光元件。提供一种包括1,2,4-三唑骨架的有机金属配合物，其中，一个N-咔唑基团通过一个苯环基团与1,2,4-三唑骨架的3-位键合，一个苯基团与1,2,4-三唑骨架的4-位键合，1,2,4-三唑骨架的2-位与铱配位，并且苯环基团与铱键合。提供一种包括上述有机金属配合物作为发射中心的发光元件。
• [EN] ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE<br/>[FR] COMPLEXE ORGANOMÉTALLIQUE, ÉLÉMENT ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTROLUMINESCENT, DISPOSITIF ÉLECTRONIQUE ET DISPOSITIF D'ÉCLAIRAGE
  申请人：SEMICONDUCTOR ENERGY LAB

  公开号：WO2016012910A1

  公开（公告）日：2016-01-28

  An object is to provide a novel organometallic complex. Another object is to provide an organometallic complex exhibiting green to blue phosphorescence. Another object is to provide an organometallic complex having deep HOMO and exhibiting green to blue phosphorescence. Another object is to provide a light-emitting element with high emission efficiency. Another object is to provide a light-emitting element exhibiting green to blue phosphorescence and having low drive voltage. To provide an organometallic complex which includes a 1,2,4-triazole skeleton and in which an N-carbazolyl group is bonded to the 3-position of the 1,2,4-triazole skeleton via a phenylene group, a phenyl group is bonded to the 4-position of the 1,2,4-triazole skeleton, the 2-position of the 1,2,4-triazole skeleton coordinates to iridium, and the phenylene group is bonded to the iridium. To provide a light-emitting element including the organometallic complex as an emission center.

  一个目标是提供一种新型的有机金属配合物。另一个目标是提供一种显示绿色到蓝色磷光的有机金属配合物。再一个目标是提供一种具有深层HOMO并能显示绿色到蓝色磷光的有机金属配合物。另一个目标是提供一种具有高发射效率的发光元件。再一个目标是提供一种显示绿色到蓝色磷光且具有低驱动电压的发光元件。提供一个包括1,2,4-三唑骨架的有机金属配合物，其中，一个N-咔唑基团通过一个苯基团连接到1,2,4-三唑骨架的3位，一个苯基团连接到1,2,4-三唑骨架的4位，1,2,4-三唑骨架的2位与铱配位，并且苯基团与铱相连。提供一个以该有机金属配合物作为发射中心的发光元件。
• Copper-Catalyzed Oxidative C–H Amination of Tetrahydrofuran with Indole/Carbazole Derivatives
  作者：Qingjing Yang、Pui Ying Choy、Wai Chung Fu、Baomin Fan、Fuk Yee Kwong

  DOI：10.1021/acs.joc.5b01990

  日期：2015.11.6

  amination of cyclic ether with indole/carbazole derivatives has been accomplished by employing copper(II) chloride/bipy as the catalyst system. In the presence of the di-tert-butyl peroxide oxidant, cyclic ethers such as tetrahydrofuran, 1,4-dioxane, and tetrahydropyran successfully undergo C–H/N–H cross dehydrogenative coupling (CDC) with various carbazole or indole derivatives in good-to-excellent yields

  通过使用氯化铜（II）/联吡啶作为催化剂体系，可以简单地将吲哚/咔唑衍生物与环状醚进行α-CH氨基化反应。在存在过氧化二叔丁基氧化剂的情况下，环醚（例如四氢呋喃，1,4-二恶烷和四氢吡喃）可以与各种咔唑或吲哚衍生物良好地成功进行C–H / N–H交叉脱氢偶联（CDC）。到出色的产量。
• Palladium-Catalyzed Intramolecular C-H Amination in Water
  作者：Lizheng Yang、Hao Li、Haifei Zhang、Hongjian Lu

  DOI：10.1002/ejoc.201601043

  日期：2016.12

  found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2 as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic

  发现钯 (II) 催化对水中的分子内 C-H 胺化有效。以 2-叠氮联苯为底物，该反应有效地提供了各种咔唑，N2 作为唯一的副产物。该反应显示出高官能团耐受性，可用于合成多种天然咔唑生物碱。催化过程受水促进，在所研究的有机溶剂中反应效率低下。