methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate | 156362-00-4

• 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: methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate
• 英文别名: methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylate；methyl 2-(2-methoxycarbonyl-1H-indole-3-yl)acetate；methyl 3-methoxycarbonylmethylindole-2-carboxylate；Methyl 2-(2-methoxycarbonyl-1H-indol-3-yl)acetate；(2-methoxycarbonyl-indol-3-yl)-acetic acid methyl ester；(2-Methoxycarbonyl-indol-3-yl)-essigsaeure-methylester
• CAS: 156362-00-4
• 化学式: C₁₃H₁₃NO₄
• mdl: MFCD14281647
• 分子量: 247.251
• InChiKey: DTWHLOFDTYAJEL-UHFFFAOYSA-N

物化性质

• 沸点：
  426.3±35.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存储在室温下

反应信息

• 作为反应物：
  描述：

  methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到3-(羧甲基)-1H-吲哚-2-羧酸
  参考文献：
  名称：

  Indole- and indoline-based kainate analogues with antagonist activity at ionotropic glutamate receptors

  摘要：

  A conformationally constrained, indole-based kainate analogue was designed based on Gouaux's X-ray structure of kainic acid bound to an iGluR2(S1S2) construct, a structural model for AMPA/kamate ionotropic glutamate receptors. In contrast to the parent kainic acid, a potent agonist, this compound, along with three structurally related analogues derived from synthetic intermediates, exhibited antagonist behavior towards KAR expressed in oocytes, a result that is rationalized by molecular modeling studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.098
• 作为产物：
  描述：

  alpha-酮戊二酸 在 盐酸 、 PPA 作用下， 以 水 为溶剂， 生成 methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indole- and indoline-based kainate analogues with antagonist activity at ionotropic glutamate receptors

  摘要：

  A conformationally constrained, indole-based kainate analogue was designed based on Gouaux's X-ray structure of kainic acid bound to an iGluR2(S1S2) construct, a structural model for AMPA/kamate ionotropic glutamate receptors. In contrast to the parent kainic acid, a potent agonist, this compound, along with three structurally related analogues derived from synthetic intermediates, exhibited antagonist behavior towards KAR expressed in oocytes, a result that is rationalized by molecular modeling studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.098

文献信息

• PdII-Catalyzed CH Olefination of N-(2-Pyridyl)sulfonyl Anilines and Arylalkylamines
  作者：Alfonso García-Rubia、Beatriz Urones、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1002/anie.201105611

  日期：2011.11.11

  N‐(2‐pyridyl)sulfonyl group acts as a removable directing group in the PdII‐catalyzed aryl CH ortho alkenylation of N‐alkyl aniline, benzylamine, and phenethylamine derivatives with electron‐poor alkenes. The products were obtained in high yields (70–90 %) and with complete regiocontrol. The mild reductive N‐sulfonyl removal enables the construction of a variety of nitrogen heterocycles. EWG=electron‐withdrawing

  柔性朋友：本ñ - （2-吡啶基）磺酰基作为在钯可拆卸的定向基团II催化的芳基C  ħ邻位 的烯基化Ñ烷基苯胺，苄胺，和苯乙胺与缺电子烯烃衍生物。获得的产品收率高（70–90％），并且具有完全的区域控制能力。温和的还原性N-磺酰基去除可构建各种氮杂环。EWG =吸电子基团。
• Visible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr₄/MeOH
  作者：Qing-Qing Yang、Marianna Marchini、Wen-Jing Xiao、Paola Ceroni、Marco Bandini

  DOI：10.1002/chem.201503787

  日期：2015.12.7

  Photocatalysis enables the cascade reactions of indoles and CBr4 in MeOH through a C(sp2)H functionalization/methanolysis sequence. The title reaction provides an efficient access to indole 2‐ and 3‐carboxylates in a single operation (no preinstallation of protecting as well as directing groups was required) with good yields under mild reaction conditions.

  光催化通过C（sp 2）H官能化/甲烷分解序列实现吲哚和CBr 4在MeOH中的级联反应。标题反应可在温和的反应条件下以高收率在一次操作中高效获得吲哚2和3-羧酸酯（无需预先安装保护基团和导向基团）。
• Synthesis of 2,3-Disubstituted Indoles by Palladium-Mediated Coupling of 2-Iodoindoles
  作者：Hidetoshi Tokuyama、Yosuke Kaburagi、Xiaoqi Chen、Tohru Fukuyama

  DOI：10.1055/s-2000-6354

  日期：——

  N-Unprotected 2-iodoindoles are synthesized by treatment of 2-stannylindoles with iodine, which in turn are prepared by tin-mediated radical cyclization of 2-alkenylphenylisocyanides. Palladium-catalyzed coupling reactions of N-unprotected 2-iodoindoles with terminal acetylenes, terminal olefins, carbonylation, and the Suzuki coupling reaction with phenyl borate proceed smoothly to furnish the corresponding 2,3-disubstituted indoles in good to excellent yields.

  N-未保护的2-碘吲哚通过将2-锡烯吲哚与碘反应合成，这些2-锡烯吲哚又是通过锡催化的自由基环化反应与2-烯基苯异氰酸酯制备的。N-未保护的2-碘吲哚与末端炔烃、末端烯烃的镍催化耦合反应，以及与苯硼酸的铃木耦合反应均顺利进行，生成相应的2,3-二取代吲哚，产率良好至优异。
• Chemical compounds
  申请人：AstraZeneca AB

  公开号：US06833387B1

  公开（公告）日：2004-12-21

  The use of a 3-substituted indole compound of formula (I) or a pharmaceutically acceptable salt, amide or ester thereof; X is CH2 or SO2 and R1, R2, R3, R4, R5, R6 and R7 are certain specified organic moieties, for use in the preparation of a medicament for the inhibition of monocyte chemoattractant protein-1 and/or RANTES induced chemotaxis. Pharmaceutical compositions containing certain compounds of formula (I) and novel compounds of formula (I) are also described and claimed.

  使用式（I）的3-取代吲哚化合物或其药学上可接受的盐、酰胺或酯；X为CH2或SO2，R1、R2、R3、R4、R5、R6和R7为特定指定的有机基团，用于制备用于抑制单核细胞趋化蛋白-1和/或RANTES诱导趋化的药物。还描述和声明了含有式（I）的某些化合物和式（I）的新化合物的药物组合物。
• Fused pyrrole derivatives
  申请人：Banner David

  公开号：US20070142452A1

  公开（公告）日：2007-06-21

  The invention is concerned with novel fused pyrrole derivatives of formula (I) wherein A, Ar, R 1 , R 2 , R 2′ and R 2″ and n are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit chymase and can be used as medicaments.

  这项发明涉及式(I)的新型融合吡咯衍生物，其中A、Ar、R1、R2、R2′和R2″以及n的定义如描述和权利要求中所定义，并且其生理上可接受的盐。这些化合物抑制chymase并可用作药物。