6-甲氧基-1,2,3,9-四氢咔唑-4-酮 | 35556-81-1

• 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
• 中文名称: 6-甲氧基-1,2,3,9-四氢咔唑-4-酮
• 英文名称: 6-methoxy-2,3-dihydro-1H-carbazol-4(9H)-one
• 英文别名: 1,2,3,9-Tetrahydro-6-methoxy-4H-carbazol-4-one；6-Methoxy-1,2,3,9-tetrahydro-carbazol-4-one；6-methoxy-1,2,3,9-tetrahydrocarbazol-4-one
• CAS: 35556-81-1
• 化学式: C₁₃H₁₃NO₂
• mdl: MFCD11168368
• 分子量: 215.252
• InChiKey: UIONPYATGROVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 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：

  6-甲氧基-1,2,3,9-四氢咔唑-4-酮 在 lithium aluminium tetrahydride 、 羟胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 2-肟氰乙酸乙酯 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 1-(9-methoxy-3,4,5,6-tetrahydro-1H-azepino[4,3-b]indol-2-yl)-3-morpholin-4-yl-propan-1-one
  参考文献：
  名称：

  开发源自具有抗血管生成作用的天然产物类似物的新型 VEGFR2 抑制剂

  摘要：

  一种新型的天然小分子 voacangine (Voa) 已被发现是一种有效的抗血管生成化合物。值得注意的是，Voa 直接结合血管内皮生长因子受体 2 (VEGFR2) 的激酶结构域，从而抑制下游信号传导。在此，我们开发了基于 Voa 独特化学结构的合成小分子，可直接特异性地靶向和调节 VEGFR2 的激酶活性。在这些 Voa 结构类似物中，Voa 类似物 19 (V19) 对 VEGF 诱导的 VEGFR2 磷酸化表现出增强的抗血管生成能力，而没有细胞毒性作用。此外，在小鼠异种移植模型中，V19 治疗导致显着的肿瘤细胞死亡。总之，这种新的 VEGFR2 调节剂受天然化合物 Voa 的刚性支架的启发，

  DOI：

  10.1021/acs.jmedchem.1c01168
• 作为产物：
  描述：

  3-氯-4-甲氧基苯胺 在 sodium amide 、 APTS 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.0h， 生成 6-甲氧基-1,2,3,9-四氢咔唑-4-酮
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• Aminoalkoxy carbazoles for the treatment of cns diseases
  申请人：Pharmacia & Upjohn Company

  公开号：US06514968B1

  公开（公告）日：2003-02-04

  The present invention provides aminoalkoxy carbazole derivatives, and more specifically, provides compounds of formula (I) wherein R1, R2, R3, R4, R8 and R9 are described herein. These compounds are 5-HT ligands, and are useful for treating diseases wherein modulation of 5-HT activity is desired.

  本发明提供氨基甲氧基咔唑衍生物，更具体地提供了式（I）中R1、R2、R3、R4、R8和R9所描述的化合物。这些化合物是5-HT配体，可用于治疗需要调节5-HT活性的疾病。
• An Improved Method for the Synthesis of Carbazolones by Palladium/Copper-Catalyzed Intramolecular Annulation of N-Arylenaminones
  作者：Jing-Hua Li、Bojie Weng、Rui Liu

  DOI：10.1055/s-0030-1258141

  日期：2010.9

  via the condensation of arylamines with 1,3-cyclodiketones followed by intramolecular oxidative cyclization catalyzed by palladium acetate and copper acetate in ethanol under an oxygen atmosphere was established. The improved method has the advantage of easily available starting materials and affords good yields. carbazolones - intramolecular oxidative cyclization - oxygen - palladium acetate - copper

  建立了一种改进的合成方法，该方法通过芳基胺与1,3-环二酮的缩合，然后在氧气气氛下由乙酸钯和乙酸铜在乙醇中催化，进行分子内氧化环化反应来合成咔唑酮。改进的方法的优点是容易获得起始原料并提供良好的产率。 卡巴唑酮-分子内氧化环化-氧气-乙酸钯-乙酸铜
• A catalyst free synthesis of 8, 9, 11-trihalo-5 H -benzofuro[3,2- c ]carbazol-10-ols
  作者：B. Ravi Shankar、V. Vijayakumar、H. Sivaramakrishnan、K. Nagarajan

  DOI：10.1016/j.tetlet.2017.09.009

  日期：2017.10

  8, 9, 11-Trichloro-5H-benzofuro[3,2-c]carbazol-10-ol analogues have been synthesized by treating 2,3-dihydro-1H-carbazol-4(9H)-one with chloranil/fluoranil without any catalyst and is found to be applicable across a range of carbazolone substrates. A possible mechanism has been proposed.

  8、9、11 -Trichloro-5 H-苯并呋喃[3,2 - c ] carbazol-10-ol类似物是通过用苯二甲腈处理2,3-dihydro-1 H -carbazol-4（9 H）-one合成的不含任何催化剂的间苯二酚/氟苯胺，发现可用于多种咔唑酮底物。已经提出了一种可能的机制。
• Carbazole derivatives and their use as 5HT-induced antagonists
  申请人：Glaxo Group Limited

  公开号：US04725615A1

  公开（公告）日：1988-02-16

  The invention relates to compounds of the general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl-(C.sub.1-4)-alkyl, C.sub.3-6 alkenyl, C.sub.3-10 alkynyl, phenyl or phenyl-(C.sub.1-3)alkyl group; one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or phenyl-(C.sub.1-3)alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; and X represents a halogen atom or a hydroxy, C.sub.1-4 alkoxy, phenyl-(C.sub.1-3)-alkoxy or C.sub.1-6 alkyl group or a group NR.sup.5 R.sup.6 or CONR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6, which may be the same or different, each represents a hydrogen atom or a C.sub.1-4 alkyl or C.sub.3-4 alkenyl group, or together with the nitrogen atom to which they are attached form a saturated 5 to 7 membered ring; and physiologically acceptable salts and solvates thereof. The compounds are potent and selective antagonists of "neuronal" 5-hydroxytryptamine receptors and are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania;); anxiety, pain; gastric stasis; symptoms of gastrointestinal dysfunction such as occur with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence; migraine; and nausea and vomiting.

  该发明涉及一般式(I)的化合物：其中R.sup.1代表氢原子或C.sub.1-10烷基，C.sub.3-7环烷基，C.sub.3-7环烷基-(C.sub.1-4)-烷基，C.sub.3-6烯基，C.sub.3-10炔基，苯基或苯基-(C.sub.1-3)烷基；由R.sup.2，R.sup.3和R.sup.4代表的基团中的一个是氢原子或C.sub.1-6烷基，C.sub.3-7环烷基，C.sub.2-6烯基或苯基-(C.sub.1-3)烷基，而另外两个基团中的每一个（可以相同也可以不同）代表氢原子或C.sub.1-6烷基；X代表卤原子或羟基，C.sub.1-4烷氧基，苯基-(C.sub.1-3)-烷氧基或C.sub.1-6烷基或基团NR.sup.5 R.sup.6或CONR.sup.5 R.sup.6，其中R.sup.5和R.sup.6（可以相同也可以不同）每个代表氢原子或C.sub.1-4烷基或C.sub.3-4烯基，或者与它们连接的氮原子一起形成饱和的5到7元环；以及其生理上可接受的盐和溶剂化合物。这些化合物是“神经元”5-羟色胺受体的强效和选择性拮抗剂，可用于治疗精神障碍（如精神分裂症和躁狂症）；焦虑，疼痛；胃排空延缓；胃肠功能障碍症状，如消化不良，消化性溃疡，反流性食道炎和胀气；偏头痛；以及恶心和呕吐。
• Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones
  作者：Rafael Bautista、Pablo Montoya、Araceli Rebollar、Eleuterio Burgueño、Joaquín Tamariz

  DOI：10.3390/molecules180910334

  日期：——

  A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted

  描述了钯催化合成咔唑骨架，包括制备 2-、5-和 7-氧化的天然和非天然咔唑生物碱。由环己烷-1,3-二酮与多种苯胺缩合生成的一系列 N-芳基环己烷烯胺酮通过 Pd(0) 催化热处理芳构化，得到相应的二芳基胺。后者被提交给 Pd(II) 催化的环化和甲基化过程，以提供所需的咔唑，包括 clausine V。按照相反的策略，还报道了一种新的和短的糖硼素全合成。