2-ethyl-9H-carbazole | 106551-62-6

• 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-ethyl-9H-carbazole
• CAS: 106551-62-6
• 化学式: C₁₄H₁₃N
• mdl: MFCD18450118
• 分子量: 195.264
• InChiKey: MLTJHZTUKWUPTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  methyl N-[6-(methoxycarbonyldiazenyl)naphthalen-2-yl]iminocarbamate 、 2-ethyl-9H-carbazole 在 C₅₁H₃₅O₄P 作用下， 以 氯仿 为溶剂， 反应 168.0h， 以49%的产率得到(S,S)-dimethyl 2,2'-(1,5-bis(2-ethyl-9H-carbazol-9-yl)naphthalene-2,6-diyl)bis(hydrazinecarboxylate)
  参考文献：
  名称：

  手性磷酸催化芳烃的Atroposelective CH胺化反应。

  摘要：

  N-芳基咔唑结构很重要，因为它们在天然产物和功能性OLED材料中普遍存在。芳烃的CH胺化反应已被公认为访问这些结构的最有效方法。涉及过渡金属催化剂的常规策略存在受限的底物通用性和外源氧化剂的需求。有机催化对映选择性CN手性轴的构造仍然难以捉摸。本文介绍的是通过氮杂萘和咔唑的组装来合成新型轴向手性N-芳基咔唑骨架的第一种有机催化策略。该反应适应广泛的底物范围，并以良好的对映体控制得到产率高的阻转异构的N-芳基咔唑。这种方法不仅提供了金属催化的CN交叉偶联的替代方法，

  DOI：

  10.1002/anie.202000585
• 作为产物：
  描述：

  2-乙酰基咔唑 在 盐酸 、 amalgamated zinc 、 苯甲醚 作用下， 生成 2-ethyl-9H-carbazole
  参考文献：
  名称：

  244. 3-乙酰基咔唑和咔唑-3-羧酸

  摘要：

  DOI：

  10.1039/jr9340001142

文献信息

• [EN] PYRAZOLE DERIVATIVES, COMPOSITIONS AND THERAPEUTIC USE THEREOF<br/>[FR] DÉRIVÉS DE PYRAZOLE, COMPOSITIONS LES COMPRENANT ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017191098A1

  公开（公告）日：2017-11-09

  Compounds of Formula (I): and salts thereof, and methods of use as Janus kinase inhibitors are described herein.

  化合物的化学式（I）及其盐，以及作为Janus激酶抑制剂的使用方法在此处描述。
• Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C-H Activation and C-N Bond Formation
  作者：Hans-René Bjørsvik、Vijayaragavan Elumalai

  DOI：10.1002/ejoc.201601191

  日期：2016.11

  An efficient method for the synthesis of the carbazole scaffold was designed and investigated. The method was developed to produce substituted carbazoles by an intramolecular combination of a free amine group and an arene. The steps of the method involved tandem Pd-catalyzed C–H activation and intramolecular C–N bond formation. The method showed good functional group tolerance, and substituent(s) could

  设计并研究了一种合成咔唑支架的有效方法。该方法被开发用于通过游离胺基团和芳烃的分子内组合来生产取代的咔唑。该方法的步骤包括串联 Pd 催化的 C-H 活化和分子内 C-N 键的形成。该方法显示出良好的官能团耐受性，并且取代基可以在2-氨基联苯底物的两个环中的任何一个或两个环上。闭环后，还原的 Pd 催化剂被过氧化氢氧化成 PdII。新方法也被证明可以很好地与相应的 2-N-乙酰氨基联苯一起使用。
• ENZYME INHIBITORS
  申请人：Davidson Alan Hornsby

  公开号：US20140163042A1

  公开（公告）日：2014-06-12

  Compounds of formula (I) are inhibitors of histone deacetylase activity, and are useful in the treatment of, for example, cancers, wherein R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxyesterase enzymes to a carboxylic acid group; R 2 is the side chain of a natural or non-natural alpha amino acid; Y is a bond, —C(═O), —S(═O) 2 —, —C(═O)O—, —C(O)NR 3 —, —C(═S)—NR 3 , —C(═NH)NR 3 or —S(═O) 2 NR 3 — wherein R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl; L 1 is a divalent radical of formula -(Alk 1 ) m (Q) n (Alk 2 ) p - wherein m, n and p are independently 0 or 1, Q is (i) an optionally substituted divalent mono- or bicyclic carbocyclic or heterocyclic radical having 5-13 ring members, or (ii), in the case where both m and p are 0, a divalent radical of formula —X 2 -Q 1 - or -Q 1 -X 2 — wherein X 2 is —O—, S— or NR A — wherein R A is hydrogen or optionally substituted C 1 -C 3 alkyl, and Q 1 is an optionally substituted divalent mono- or bicyclic carbocyclic or heterocyclic radical having 5-13 ring members, Alk 1 and Alk 2 independently represent optionally substituted divalent C 3 -C 7 cycloalkyl radicals, or optionally substituted straight or branched, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, or C 2 -C 6 alkynylene radicals which may optionally contain or terminate in an ether (—O—), thioether (—S—) or amino (—NR A —) link wherein R A is hydrogen or optionally substituted C 1 -C 3 alkyl; X 1 represents a bond; —C(═O); or —S(═O) 2 —; —NR 4 C(═O)—, —C(═O)NR 4 —, —NR 4 C(═O)NR 5 —, —NR 4 S(═O) 2 —, or —S(═O) 2 NR 4 — wherein R 4 and R 5 are independently hydrogen or optionally substituted C 1 -C 6 alkyl; z is 0 or 1; A represents an optionally substituted mono-, bi- or tri-cyclic carbocyclic or heterocyclic ring system wherein the radicals R 1 R 2 NH—Y-L 1 -X 1 -[CH 2 ] Z — and HONHCO-[LINKER]- are attached different ring atoms; and -[Linker]- represents a divalent linker radical linking a ring atom in A with the hydroxamic acid group CONIIOII, the length of the linker radical, from the terminal atom linked to the ring atom of A to the terminal atom linked to the hydroxamic acid group, is equivalent to that of an unbranched saturated hydrocarbon chain of from 3-10 carbon atoms.

  式(I)的化合物是组蛋白去乙酰化酶活性抑制剂，可用于治疗癌症等疾病，其中R1是羧酸基（-COOH）或可由一个或多个细胞内羧酸酯酶水解为羧酸基的酯基；R2是天然或非天然α氨基酸的侧链；Y是键，-C（=O），-S（=O）2-，-C（=O）O-，-C（=O）NR3-，-C（=S）-NR3，-C（=NH）NR3或-S（=O）2NR3-，其中R3是氢或可选取代的C1-C6烷基；L1是式-(Alk1)m(Q)n(Alk2)p-的二价基团，其中m、n和p独立地为0或1，Q是（i）一个可选取代的二价单环或双环碳环或杂环基团，具有5-13个环成员，或（ii）在m和p均为0的情况下，是式-Q1-X2-或-X2-Q1-的二价基团，其中X2是-O-，-S-或-NRA-，其中RA是氢或可选取代的C1-C3烷基，Q1是可选取代的二价单环或双环碳环或杂环基团，具有5-13个环成员，Alk1和Alk2独立地表示可选取代的二价C3-C7环烷基基团，或可选取代的直链或支链，C1-C6烷基，C2-C6烯基或C2-C6炔基基团，其可以可选地含有或终止于醚（-O-），硫醚（-S-）或氨基（-NRA-）链，其中RA是氢或可选取代的C1-C3烷基；X1表示键，-C（=O）或-S（=O）2-；-NR4C（=O）-，-C（=O）NR4-，-NR4C（=O）NR5-，-NR4S（=O）2-或-S（=O）2NR4-，其中R4和R5独立地为氢或可选取代的C1-C6烷基；z为0或1；A表示可选取代的单环、双环或三环碳环或杂环系统，其中基团R1R2NH-Y-L1-X1-[CH2]Z-和HONHCO-[LINKER]-附着在不同的环原子上；-[Linker]-表示将A中的一个环原子与羟酰胺酸基团CONIIOII连接的二价连接基团，连接基团的长度，从连接到A环原子的末端原子到连接到羟酸胺基团的末端原子，相当于从3-10个碳原子的直链饱和碳氢链的长度。
• Enzyme Inhibitors
  申请人：Davidson Alan Hornsby

  公开号：US20090291978A1

  公开（公告）日：2009-11-26

  Compounds of formula (I) are inhibitors of histone deacetylase activity, and are useful in the treatment of, for example, cancers, wherein R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxyesterase enzymes to a carboxylic acid group; R 2 is the side chain of a natural or non-natural alpha amino acid; Y is a bond, C(═O)—, —S(═O) 2 —, —C(—O)O—, —C(O)NR 3 —, —C(═S)—NR 3 , —C(═NH)NR 3 or —S(═O) 2 NR 3 — wherein R 3 is hydrogen or optionally substituted C 1 -C 6 alkyl; L is a divalent radical of formula -(Alk 1 ) m (O) n (Alk 2 ) p — wherein m, n and p are independently 0 or 1, Q is (i) an optionally substituted divalent mono- or bicyclic carbocyclic or heterocyclic radical having 5-13 ring members, or (ii), in the case where both m and p are 0, a divalent radical of formula —X 2 -Q 1 - or -Q 1 -X 2 — wherein X 2 is —O—, S— or NR A — wherein R A is hydrogen or optionally substituted C 1 -C 3 alkyl, and Q 1 is an optionally substituted divalent mono- or bicyclic carbocyclic or hetero-cyclic radical having 5-13 ring members, AIk 1 and AIk 2 independently represent optionally substituted divalent C 3 -C 7 cycloalkyl radicals, or optionally substituted straight or branched, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, or C 2 -C 6 alkynylene radicals which may optionally contain or terminate in an ether (—O—), thioether (—S—) or amino (—NR A -) link wherein R A is hydrogen or optionally substituted C 1 -C 3 alkyl; X represents a bond; —C(═O); or —S(═O) 2 —; —NR 4 C(═O)—, —C(═O)NR 4 —, —NR 4 C(═O)NR 5 —, —NR 4 S(═O) 2 —, or —S(═O) 2 NR 4 — wherein R 4 and R 5 are independently hydrogen or optionally substituted C 1 -C 6 alkyl; z is 0 or 1; A represents an optionally substituted mono-, bi- or tri-cyclic carbocyclic or heterocyclic ring system wherein the radicals R 1 R 2 NH—Y-L 1 -X 1 —[CH 2 ] z — and HONHCO-[LINKER]- are attached different ring atoms; and -[Linker]- represents a divalent linker radical linking a ring atom in A with the hydroxamic acid group CONHOH, the length of the linker radical, from the terminal atom linked to the ring atom of A to the terminal atom linked to the hydroxamic acid group, is equivalent to that of an unbranched saturated hydrocarbon chain of from 3-10 carbon atoms.

  式(I)的化合物是组蛋白去乙酰化酶抑制剂，可用于治疗癌症等疾病，其中R1是羧酸基（-COOH）或一个可被一个或多个细胞内羧酸酯酶水解为羧酸基的酯基；R2是天然或非天然α氨基酸的侧链；Y是键，C（═O）—，—S（═O）2—，—C（—O）O—，—C（O）NR3—，—C（═S）—NR3，—C（═NH）NR3或—S（═O）2NR3—，其中R3是氢或可选择性取代的C1-C6烷基；L是式-(Alk1)m(O)n(Alk2)p-的二价基团，其中m、n和p分别独立为0或1；Q是（i）一个可选择性取代的二价单环或双环碳环或杂环基团，其具有5-13个环成员，或（ii）在m和p都为0的情况下，是式—X2-Q1-或-Q1-X2—的二价基团，其中X2是—O—，S—或NRA—，其中RA是氢或可选择性取代的C1-C3烷基，Q1是一个可选择性取代的二价单环或双环碳环或杂环基团，其具有5-13个环成员，Alk1和Alk2独立地表示可选择性取代的二价C3-C7环烷基基团，或可选择性取代的直链或支链C1-C6烷基、C2-C6烯基或C2-C6炔基基团，其可以选择性地包含或终止于醚（-O-）、硫醚（-S-）或氨基（-NRA-）链，其中RA是氢或可选择性取代的C1-C3烷基；X表示键，—C（═O）；或—S（═O）2—；—NR4C（═O）—，—C（═O）NR4—，—NR4C（═O）NR5—，—NR4S（═O）2—或—S（═O）2NR4—，其中R4和R5独立地为氢或可选择性取代的C1-C6烷基；z为0或1；A表示可选择性取代的单环、双环或三环碳环或杂环系统，其中基团R1R2NH—Y-L1-X1—[CH2]z—和HONHCO-[LINKER]-附着于不同的环原子上；-[Linker]-表示连接A中的一个环原子与羟酰胺酸基团CONHOH的二价连接基团，连接基团的长度，从连接到A环原子的末端原子到连接到羟酸胺基团的末端原子，相当于3-10个碳原子的直链饱和烃链的长度。
• SUBSTITUTED BIPYRIDINES FOR USE IN ORGANIC LIGHT-EMITTING DEVICES
  申请人：Sisk David T.

  公开号：US20120179089A1

  公开（公告）日：2012-07-12

  Optionally substituted bipyridine compounds, optionally substituted phenylbipyridine compounds, or optionally substituted bis-phenylbipyridine compounds may be useful in light-emitting devices. Some examples include, but are not limited to, optionally substituted 4-(5-(6-(4-(diphenylamino)phenyl)pyridin-3-yl)pyridin-2-yl)-N,N-diphenylbenzenamine, optionally substituted 9-(4-(5-(6-(4-(9H-carbazol-9-yl)phenyl)pyridin-3-yl)pyridin-2-yl)phenyl)-9H-carbazole, optionally substituted 4-(5-(6-(benzo[d]thiazol-2-yl)pyridin-3-yl)pyridin-2-yl)-N,N-diphenylbenzenamine, optionally substituted 4-(5-(6-(benzo[d]oxazol-2-yl)pyridin-3-yl)pyridin-2-yl)-N,N-diphenylbenzenamine, optionally substituted N,N-diphenyl-4-(5-(6-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)pyridin-2-yl)benzenamine, optionally substituted 4-(5-(6-(4-(9H-carbazol-9-yl)phenyl)pyridin-3-yl)pyridin-2-yl)-N,N-diphenylbenzenamine, optionally substituted 2-(5-(6-(benzo[d]thiazol-2-yl)pyridin-3-yl)pyridin-2-yl)benzo[d]thiazole, optionally substituted 2-(5-(6-(benzo[d]thiazol-2-yl)pyridin-3-yl)pyridin-2-yl)benzo[d]oxazole, optionally substituted 9-(4-(5-(6-(benzo[d]thiazol-2-yl)pyridin-3-yl)pyridin-2-yl)phenyl)-9H-carbazole, optionally substituted 9-(4-(5-(6-(benzo[d]oxazol-2-yl)pyridin-3-yl)pyridin-2-yl)phenyl)-9H-carbazole, optionally substituted 9-(4-(6′-(1-phenyl-1H-benzo[d]imidazol-2-yl)-3,3′-bipyridin-6-yl)phenyl)-9H-carbazole, and 6,6′-bis(9-phenyl-9H-carbazol-3-yl)-3,3′-bipyridine.

  可选取代的联吡啶化合物、可选取代的苯基联吡啶化合物或可选取代的双苯基联吡啶化合物可用于发光装置。一些例子包括但不限于可选取代的4-(5-(6-(4-(二苯胺)苯基)吡啶-3-基)吡啶-2-基)-N,N-二苯基苯胺、可选取代的9-(4-(5-(6-(4-(9H-咔唑-9-基)苯基)吡啶-3-基)吡啶-2-基)苯基)-9H-咔唑、可选取代的4-(5-(6-(苯并[d]噻唑-2-基)吡啶-3-基)吡啶-2-基)-N,N-二苯基苯胺、可选取代的4-(5-(6-(苯并[d]噻唑-2-基)吡啶-3-基)吡啶-2-基)-N,N-二苯基苯胺、可选取代的N,N-二苯基-4-(5-(6-(1-苯基-1H-苯并[d]咪唑-2-基)吡啶-3-基)吡啶-2-基)苯胺、可选取代的4-(5-(6-(4-(9H-咔唑-9-基)苯基)吡啶-3-基)吡啶-2-基)-N,N-二苯基苯胺、可选取代的2-(5-(6-(苯并[d]噻唑-2-基)吡啶-3-基)吡啶-2-基)苯并[d]噻唑、可选取代的2-(5-(6-(苯并[d]噻唑-2-基)吡啶-3-基)吡啶-2-基)苯并[d]噁唑、可选取代的9-(4-(5-(6-(苯并[d]噻唑-2-基)吡啶-3-基)吡啶-2-基)苯基)-9H-咔唑、可选取代的9-(4-(5-(6-(苯并[d]噁唑-2-基)吡啶-3-基)吡啶-2-基)苯基)-9H-咔唑、可选取代的9-(4-(6′-(1-苯基-1H-苯并[d]咪唑-2-基)-3,3′-联吡啶-6-基)苯基)-9H-咔唑和6,6′-双(9-苯基-9H-咔唑-3-基)-3,3′-联吡啶。