4-羟基-1H-吲哚-6-羧酸甲酯 | 77140-48-8

• 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: 4-羟基-1H-吲哚-6-羧酸甲酯
• 中文别名: 4-羟基吲哚-6-羧酸甲酯；4-羟基-6-甲酸甲酯吲哚
• 英文名称: 4-hydroxy-1H-indole-6-carboxylic acid methyl ester
• 英文别名: methyl 4-hydroxy-1H-indole-6-carboxylate；methyl 4-hydroxyindole-6-carboxylate；4-hydroxy-6-methoxycarbonyl-indole
• CAS: 77140-48-8
• 化学式: C₁₀H₉NO₃
• mdl: MFCD04973985
• 分子量: 191.186
• InChiKey: YCLHTEHHXRJHKC-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149℃ (dichloromethane )

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-羟基-1H-吲哚-6-羧酸甲酯 生成 methyl 4-[3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropoxy]-1H-indole-6-carboxylate
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙酰氧基吲哚-6-羧酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以4.23 g的产率得到4-羟基-1H-吲哚-6-羧酸甲酯
  参考文献：
  名称：

  A Reinvestigation of 4-Hydroxyindole-6-carboxylate Synthesis from Pyrrole-2-carboxaldehyde:  A Facile Synthesis of Indoles and Indolizines

  摘要：

  Cyclization of the Stobbe product 3 under the literature conditions (acetic anhydride/sodium acetate) affords both the indole 6 and the indolizine 8. The presence of base promotes the formation of indolizine products, and using acetic anhydride/triethylamine leads to indolizine products in good yield. Improved conditions for conversion to indoles 2, 5, and 6 are reported, and inconsistencies in some of the literature structure assignments and characterization data are noted.

  DOI：

  10.1021/jo040191e

文献信息

• [EN] NEW OCTAHYDRO-CYCLOBUTA [1,2-c;3,4-c']DIPYRROL-2-YL<br/>[FR] NOUVEL OCTAHYDRO-CYCLOBUTA [1,2-C; 3,4-C'] DIPYRROL-2-YL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015078803A1

  公开（公告）日：2015-06-04

  The invention provides novel compounds having the general formula (I) wherein R1, Y and R2 are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有一般式（I）的新化合物，其中R1、Y和R2如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• Novel indolyl derivatives which are L-CPT1 inhibitors
  申请人：Ackermann Jean

  公开号：US20070060567A1

  公开（公告）日：2007-03-15

  The invention is concerned with novel heterobicyclic derivatives of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, X and Y are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit L-CPT1 and can be used as medicaments.

  这项发明涉及式(I)的新异双环衍生物： 其中R1、R2、R3、R4、R5、R6、R7、A、X和Y的定义如描述和权利要求中所述，以及其生理上可接受的盐和酯。这些化合物抑制L-CPT1，可用作药物。
• Rh(iii)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C–H activation
  作者：Zhuangzhi Shi、Mélissa Boultadakis-Arapinis、Dennis C. Koester、Frank Glorius

  DOI：10.1039/c4cc00029c

  日期：——

  Biologically interesting fused oligocyclic lactams have been prepared via an intramolecular redox-neutral cyclization process. By the proper choice of the substrates with a wide variety of tethered olefins, the less favored C–H bond can be activated and functionalized. This C–H activation proceeds under mild conditions, obviates the need for external oxidants, and displays a broad scope with respect to the substituents.

  生物学上引人关注的融合多环内酰胺已通过一种分子内氧化还原中性环化过程制备。通过适当选择带有多种侧链烯烃的底物，可以激活并功能化较不利的C-H键。这种C-H键的活化在温和条件下进行，无需外部氧化剂，并且对取代基具有广泛的适用性。
• Synthesis of amide isosteres of schweinfurthin-based stilbenes
  作者：David P. Stockdale、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2017.08.016

  日期：2017.10

  The schweinfurthins are plant-derived stilbenes with an intriguing profile of anti-cancer activity. To obtain analogues of the schweinfurthins that might preserve the biological activity but have greater water solubility, a formal replacement of the central olefin with an amide has been explored. Two pairs of amides have been prepared, each containing the same hexahydroxanthene “left half” joined through

  schweinfurthins是植物来源的对苯二酚，具有令人着迷的抗癌活性。为了获得可能保留生物活性但具有更大水溶性的美白四氢呋喃类似物，已经研究了用酰胺正式取代中心烯烃。制备了两对酰胺，每对酰胺都包含相同的六氢氧杂蒽“左半部分”，通过酰胺键连接到两个不同的“右半部分”。在每个系列中，酰胺均以两种可能的方向插入，将羰基置于三环ABC环系统上，胺置于D环上，或胺置于六氢氧杂蒽上，羰基位于D环上。四种新的Schwweinfurthin类似物已在NCI 60细胞株筛选中进行了测试，
• Pyrimidinyl methyl indole derivatives with antibacterial activity
  申请人：——

  公开号：US20030119857A1

  公开（公告）日：2003-06-26

  This invention relates to indole derivatives of the general formula (I) wherein R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, dialkylsulfamoyl, N-cycloalkyl-N-alkylsulfamoyl, heterocyclylalkyl or phenylalkyl; R 2 is hydrogen, halogen, alkyl, alkanoyl, phenyl, phenylalkyl or heterocyclylalkyl; R 3 is hydrogen, alkyl; and R 4 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, dialkylsulfamoyl, N-cycloalkyl-N-alkylsulfamoyl, heterocyclylalkyl, or phenylalkyl; and pharmaceutically acceptable acid addition salts of these compounds, there use as therapeutically active substances; medicaments based on these substances, optionally in combination with sulphonamides, and their production; the use of these substances as medicaments and for the production of antibacterially-active medicaments; as well as the manufacture of the compounds of formula (I) and their pharmaceutically acceptable acid addition salts and intermediates for their manufacture.

  这项发明涉及通式（I）的吲哚衍生物，其中R1是烷基，烯基，炔基，环烷基，环烷基烷基，烷基磺酰基，环烷基磺酰基，环烷基烷基磺酰基，二烷基磺酰胺基，N-环烷基-N-烷基磺酰胺基，杂环烷基烷基或苯基烷基；R2是氢，卤素，烷基，醇酰基，苯基，苯基烷基或杂环烷基烷基；R3是氢，烷基；以及R4是烷基，烯基，炔基，环烷基，环烷基烷基，烷基磺酰基，环烷基磺酰基，环烷基烷基磺酰基，二烷基磺酰胺基，N-环烷基-N-烷基磺酰胺基，杂环烷基烷基或苯基烷基；以及这些化合物的药学上可接受的酸盐，它们作为治疗活性物质的用途；基于这些物质的药物，可选地与磺胺类药物结合，以及它们的生产；这些物质作为药物以及用于生产抗菌活性药物的用途；以及通式（I）化合物及其药学上可接受的酸盐的制造，以及用于其制造的中间体。