ethyl 1,2-dimethylindole-3-carboxylate | 20357-14-6

• 物质功能分类: 医药中间体
• 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: ethyl 1,2-dimethylindole-3-carboxylate
• 英文别名: ethyl 1,2-dimethyl-1H-indole-3-carboxylate
• CAS: 20357-14-6
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD00448247
• 分子量: 217.268
• InChiKey: RQRUAENQOVZHNW-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  342.2±22.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1,2-dimethylindole-3-carboxylate 在 palladium on activated charcoal 氢气 、 phosphorus pentoxide 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 为溶剂， -78.0~110.0 ℃ 、275.79 kPa 条件下， 反应 5.0h， 生成 5,7-dimethyl-5,6,7,12-tetrahydrobenzo[4,5]cyclohepta[b]indol-12-one
  参考文献：
  名称：

  Mouaddib, Abderrahim; Joseph, Benoit; Hasnaoui, Aissa, Heterocycles, 1999, vol. 51, # 9, p. 2127 - 2137

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl acetoacetate N-methyl-N-phenylhydrazone 在 盐酸 作用下， 生成 ethyl 1,2-dimethylindole-3-carboxylate
  参考文献：
  名称：

  418.吲哚乙酸的合成

  摘要：

  DOI：

  10.1039/jr9340001901

文献信息

• [EN] COMPOUNDS HAVING ACTIVITY AT 5HT2C RECEPTOR AND USES THEREOF<br/>[FR] COMPOSES AYANT UNE ACTIVITE AU NIVEAU DU RECEPTEUR 5HT2C ET LEURS UTILISATIONS
  申请人：GLAXO GROUP LTD

  公开号：WO2004081010A1

  公开（公告）日：2004-09-23

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein Q is phenyl or a 6-membered heteroaromatic group containing at least one nitrogen atom; A is -(CH2-CH2)-, -(CH=CH)-, -(CH2)3-, -C(CH3)2-, -(CH=CH-CH2)-, or a group -(CHR3)- wherein R3 is hydrogen, halogen, hydroxy, cyano, nitro, C1-6alkyl, C3-7cycloalkyl, C3-7cycloalkyloxy, haloC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy or C1-6alkylthio; B is O, S or NR11, wherein R11 is hydrogen, C1-6alkyl optionally substituted by C1-6alkoxy, or is C1-6alkanoyl optionally substituted by C1-6alkoxy; R1 is halogen, cyano, C1-6alkyl, C3-7cycloalkyl, C3-7cycloalkyloxy, C1-6alkoxy, C1-6alkylthio, hydroxy, amino, mono- or di-C1- 6alkylamino, an N-linked 4 to 7 membered heterocyclic group, nitro, haloC1-6alkyl, haloC1-6alkoxy, aryl, arylC1-6alkyl, arylC1-6alkyloxy, arylC1-6alkylthio, COR4 (wherein R4 is amino, mono- or di-C1-6alkylamino or an N-linked 4 to 7 membered heterocyclic group), COOR5 or COR6 (wherein R5 and R6 are independently hydrogen or C1-6alkyl); p is 0, 1 or 2 or 3; R2 is hydrogen, halogen, hydroxy, cyano, nitro, C1-6alkyl, C1-6alkanoyl, C3-7cycloalkyl, C3-7cycloalkyloxy, haloC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, C1-6alkylthio, amino, mono- or di-C1-6alkylamino or an N-linked 4 to 7 membered heterocyclic group; X is oxygen, sulfur, -CH2- or NR8 wherein R8 is hydrogen or C1-6alkyl; Y is a single bond, -CH2-, -(CH2)2- or -CH=CH-; and Z is an optionally substituted N-linked heterocyclic group or a C-linked 4 to 7 membered heterocyclic group containing at least one nitrogen, or Z is -NR9R10 where R9 and R10 are independently hydrogen or C1-6alkyl. Method of preparation and uses thereof in therapy, such as for example in treatment of depression and anxiety, are also disclosed.

  公开了具有式（I）的化合物及其药学上可接受的盐：其中Q是苯或含有至少一个氮原子的6元杂芳基团；A是-(CH2-CH2)-，-(CH=CH)-，-(CH2)3-，-C(CH3)2-，-(CH=CH-CH2)-，或一个-(CHR3)-基团，其中R3是氢，卤素，羟基，氰基，硝基，C1-6烷基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基或C1-6烷基硫基；B是O，S或NR11，其中R11是氢，C1-6烷基，可选择地被C1-6烷氧基取代，或是C1-6烷酰基，可选择地被C1-6烷氧基取代；R1是卤素，氰基，C1-6烷基，C3-7环烷基，C3-7环烷氧基，C1-6烷氧基，C1-6烷基硫基，羟基，氨基，单或双C1-6烷基氨基，N-连接的4到7成员杂环基团，硝基，卤代C1-6烷基，卤代C1-6烷氧基，芳基，芳基C1-6烷基，芳基C1-6烷氧基，芳基C1-6烷硫基，COR4（其中R4是氨基，单或双C1-6烷基氨基或N-连接的4到7成员杂环基团），COOR5或COR6（其中R5和R6独立地是氢或C1-6烷基）；p是0，1，2或3；R2是氢，卤素，羟基，氰基，硝基，C1-6烷基，C1-6烷酰基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C1-6烷基硫基，氨基，单或双C1-6烷基氨基或N-连接的4到7成员杂环基团；X是氧，硫，-CH2-或NR8，其中R8是氢或C1-6烷基；Y是单键，-CH2-，-(CH2)2-或-CH=CH-；Z是一个可选择地取代的N-连接杂环基团或含有至少一个氮的C-连接的4到7成员杂环基团，或Z是-NR9R10，其中R9和R10独立地是氢或C1-6烷基。还公开了其制备方法及在治疗中的用途，例如在抑郁症和焦虑症的治疗中。
• PYRROLO- AND THIAZOLO-PYRIDINE COMPOUNDS, AND METHODS OF USE THEREOF
  申请人：DENG Shaojiang

  公开号：US20080004309A1

  公开（公告）日：2008-01-03

  The present invention relates to novel compounds capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  这项发明涉及一种能够调节缺氧诱导因子（HIF）稳定性和/或活性的新化合物。
• Synthesis of 6,7-dihydrobenzo[4,5]cyclohept-[1,2-<i>b</i>]indol-12(5<i>H</i>)-one and related compounds
  作者：B. Joseph、O. Cornec、J.-Y. Mérour、X. Solans、M. Font-Bardia

  DOI：10.1002/jhet.5570340229

  日期：1997.3

  The synthetic routes of 6,7-dihydrobenzo[4,5]cyclohept[1,2-b]indol-12(5H)-one 5 from either 1-methyl or 1-sulfonylindole-2-carboxaldehyde 1 or ethyl 1,2-dimethylindole-3-carboxylate 6 are reported. The structure of the ketone 5a was confirmed by X-ray crystallography. Several indole derivatives have been prepared with potential antitumor activity.

  由1-甲基或1-磺基吲哚-2-羧醛1或乙基1,6,7-二氢苯并[4,5]环庚[1,2 - b ]吲哚-12（5H）-1 5的合成路线报道了2-二甲基吲哚-3-羧酸酯6。酮5a的结构通过X射线晶体学确认。已经制备了具有潜在抗肿瘤活性的几种吲哚衍生物。
• A novel synthesis of quinazolinequinone and carbazolequinone through anionic cycloaddition: its application to a synthesis of murrayaquinone A.
  作者：Akimori WADA、Syuichi HIRAI、Miyoji HANAOKA

  DOI：10.1248/cpb.42.416

  日期：——

  A novel synthesis of the quinazolinequinone (5) and the carbazolequinone (9) is described. Anionic cycloaddition of the heterocyclic esters (1 and 6) with phenyl β-trimethylsilylvinyl sulfone (2c) afforded the cycloadducts (3 and 7), which were converted to the quinones (5 and 9) via the phenols (4 and 8). This method was applied to a covenient synthesis of murrayaquinone A (10).

  描述了喹唑啉醌(5)和咔唑醌(9)的一种新合成方法。将杂环酯(1和6)与苯基β-三甲基硅基乙烯基砜(2c)进行阴离子环加成得到环加成产物(3和7)，然后通过酚类化合物(4和8)转化为醌类化合物(5和9)。这种方法被应用于murrayaquinone A (10)的便捷合成。
• Three-component spiropyran synthesis via tandem alkylation-condensation
  作者：Harriet Swinson、Alexis Perry

  DOI：10.1016/j.tet.2020.131219

  日期：2020.6

  A catalyst-free, three-component alkylation-condensation cascade for spiropyran synthesis has been developed, using readily available building blocks (indoles, alkyl halides, salicylaldehydes) and environmentally benign solvents (water, ethanol). A cascade approach enables this sequence to proceed under mild conditions which, in turn, promote broad substrate tolerance and operational simplicity. Consequently

  已经开发出了无催化剂的螺吡喃合成三组分烷基化-缩合级联反应，使用容易获得的结构单元（吲哚，烷基卤化物，水杨醛）和环境友好的溶剂（水，乙醇）。级联方法使该序列可以在温和的条件下进行，从而促进广泛的底物耐受性和操作简便性。因此，我们已经证明了该方法在合成25种结构多样的螺吡喃中的效用，并在整个螺吡喃框架中并以多克规模整合了有用的功能。