3-Dimethylaminomethyl-2-methoxycarbonylindole | 113772-32-0

• 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: 3-Dimethylaminomethyl-2-methoxycarbonylindole
• 英文别名: methyl 3-[(dimethylamino)methyl]-1H-indole-2-carboxylate
• CAS: 113772-32-0
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: JNTGGPPLKYBQAL-UHFFFAOYSA-N

物化性质

• 沸点：
  381.5±32.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Dimethylaminomethyl-2-methoxycarbonylindole 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Construction of Three Building Blocks for the Total Synthesis of Microsclerodermins

  摘要：

  三个构建模块2、3和4已高效地从羧酸6、14和20分别合成，用于微硬皮素（1）的总合成。

  DOI：

  10.1055/s-1999-2651
• 作为产物：
  描述：

  吲哚-2-羧酸 在 potassium hydrogencarbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Dimethylaminomethyl-2-methoxycarbonylindole
  参考文献：
  名称：

  Construction of Three Building Blocks for the Total Synthesis of Microsclerodermins

  摘要：

  三个构建模块2、3和4已高效地从羧酸6、14和20分别合成，用于微硬皮素（1）的总合成。

  DOI：

  10.1055/s-1999-2651

文献信息

• Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives
  作者：Min Zhu、Chao Zheng、Xiao Zhang、Shu-Li You

  DOI：10.1021/jacs.8b12965

  日期：2019.2.13

  intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The

  通过能量转移机制实现了基于可见光促进的 [2+2] 环加成的吲哚衍生物的分子内脱芳构化。在热条件下通常无法获得的高度应变的环丁烷稠合角四环螺二氢吲哚可以在温和条件下以高产率（高达 99%）和优异的非对映选择性（>20:1 dr）直接获得。该方法还与不同的官能团兼容，并且可以灵活转换。此外，DFT 计算为底物的合理设计和对反应途径的深入理解提供了指导。通过利用可见光诱导的激发态反应性，该过程构成了吲哚功能化的罕见例子。
• Cyclometallation of indole derivatives: cyclopalladation of gramine and 1-methyl gramine and CO insertion
  作者：Stefano Tollari、Francesco Demartin、Sergio Cenini、Giovanni Palmisano、Paolo Raimondi

  DOI：10.1016/s0022-328x(96)06630-2

  日期：1997.1

  Li2PdCl4, in methanol, with gramine 1 and 1-methyl gramine 2 gave the dimeric complexes 1a and 2a with chlorine bridges and having the indole nucleus metallated at position 2. The corresponding bromo derivatives 1b and 2b were isolated from the reactions of Pd(OAc)2 with 1 and 2, followed by treatment with LiBr. Complexes 1a,b and 2a,b gave the monomeric, cyclometallated derivatives 3a-d by reaction

  Li 2 PdCl 4在甲醇中与氨基甲酸酯1和1-甲基氨基甲酸酯2形成带有氯桥的二聚配合物1a和2a，并且吲哚核在位置2处金属化。从以下化合物的反应中分离出相应的溴衍生物1b和2b： Pd（OAc）2与1和2，然后用LiBr处理。配合物1a，b和2a，b通过与PPh 3反应得到单体的环金属化衍生物3a-d。在二氯甲烷中。当在AcOna存在下使PdCl 2，PPh 3和2在甲醇中反应来尝试1-甲基氨基甲胺1的环palpalladation时，获得了意外的化合物4。的结构测定4表明它由已知的[的Pd（PPh的3）氯3 ] -阴离子填充有二甲基-双（3-亚甲基-1-甲基吲哚）铵阳离子。
• Tryptamine compounds, and methods of cerebrovascular treatment therewith
  申请人：Beecham-Wuelfing GmbH & Co. KG

  公开号：US04980368A1

  公开（公告）日：1990-12-25

  A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: R.sub.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen; R.sub.2 and R.sub.3 are both hydrogen or together represent a bond; R.sub.4 is selected from C.sub.1-6 alkyl, phenyl, phenyl C.sub.1-4 alkyl, COR.sub.8 where R.sub.8 is hydroxy, C.sub.1-6 alkoxy or NR.sub.9 R.sub.10 where R.sub.9 and R.sub.10 are independently hydrogen or C.sub.1-4 alkyl and CH.sub.2 OR.sub.11 and R.sub.11 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkanoyl; R.sub.5 is hydrogen, C.sub.1-6 alkyl or phenyl C.sub.1-4 alkyl; R.sub.6 is phenyl C.sub.1-7 alkyl in which the phenyl moiety is optionally substituted by one or two of halogen, ortho-nitro, meta- or para-methoxy, methyl or NR.sub.12 R.sub.13 wherein R.sub.12 and R.sub.13 are independently hydrogen or C.sub.1-6 alkyl or R.sub.12 and R.sub.13 together are C.sub.2-6 polymethylene or the phenyl moiety is 3,4-disubstituted by methylenedioxy or ethylenedioxy; and R.sub.7 is hydrogen or C.sub.1-4 alkyl, processes for its preparation and its use as a pharmaceutical.

  式(I)的化合物或其药学上可接受的盐： 其中，R.sub.1是氢、C.sub.1-6烷基、C.sub.1-6烷氧基或卤素；R.sub.2和R.sub.3都是氢或者一起代表一个键；R.sub.4选自C.sub.1-6烷基、苯基、苯基C.sub.1-4烷基、COR.sub.8，其中R.sub.8是羟基、C.sub.1-6烷氧基或NR.sub.9R.sub.10，其中R.sub.9和R.sub.10独立地是氢或C.sub.1-4烷基和CH.sub.2OR.sub.11，R.sub.11是氢、C.sub.1-4烷基或C.sub.1-4酰基；R.sub.5是氢、C.sub.1-6烷基或苯基C.sub.1-4烷基；R.sub.6是苯基C.sub.1-7烷基，其中苯基部分可以选择地被卤素、邻硝基、间或对甲氧基、甲基或NR.sub.12R.sub.13取代，其中R.sub.12和R.sub.13独立地是氢或C.sub.1-6烷基或R.sub.12和R.sub.13一起是C.sub.2-6聚亚甲基或苯基部分是3,4-二取代的亚甲基二氧基或乙二氧基；R.sub.7是氢或C.sub.1-4烷基，其制备方法以及其作为药物的用途。
• 3-(2-Aminoethyl)indole and -indoline derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：SMITHKLINE BEECHAM PHARMA GmbH

  公开号：EP0233413A2

  公开（公告）日：1987-08-26

  A compound of formula (1) or a pharmaceutically acceptable salt thereof: wherein: R, is hydrogen, C1-6 alkyl, C1-6 alkoxy or halogen; R2 and R3 are both hydrogen or together represent a bond; R4 is selected from C1-6 alkyl, phenyl, phenyl-C1-4 alkyl, CORe where R8 is hydroxy, C1-6 alkoxy or NR9R10 where R9 and R10 are independently hydrogen or C1-4 alkyl and CH2OR11 where R11 is hydrogen, C1-4 alkyl or C1-4 alkanoyl; R6 is hydrogen, C1-6 alkyl or phenyl C1-4 alkyl; R6 is phenyl C1-7 alkyl in which the phenyl moiety is optionally substituted by one or two of halogen, ortho-nitro. meta-or para-methoxy, methyl or NR12R13 wherein R12 and R13 are independently hydrogen or C1-6 alkyl or R12 and R13 together are C2-6 polymethylene or the phenyl moiety is 3,4- disubstituted by methylenedioxy or ethylenedioxy; and R7 is hydrogen or C1-4 alkyl, processes for its preparation and its use as a pharmaceutical.

  式 (1) 的化合物或其药学上可接受的盐： 其中 R，是氢、C1-6 烷基、C1-6 烷氧基或卤素； R2 和 R3 都是氢或共同代表一个键； R4 选自 C1-6 烷基、苯基、苯基-C1-4 烷基、CORe（其中 R8 为羟基）、C1-6 烷氧基或 NR9R10（其中 R9 和 R10 独立地为氢或 C1-4 烷基）和 CH2OR11（其中 R11 为氢、C1-4 烷基或 C1-4 烷酰基）； R6 是氢、C1-6 烷基或苯基 C1-4 烷基； R6 是苯基 C1-7 烷基，其中苯基可选择被卤素、正硝基、偏甲氧基或对甲氧基、甲基或 NR12R13 中的一个或两个取代，其中 R12 和 R13 独立地为氢或 C1-6 烷基，或 R12 和 R13 合在一起为 C2-6 聚亚甲基，或苯基被亚甲二氧基或亚乙二氧基 3,4- 二取代；以及 R7是氢或C1-4烷基，其制备工艺及其作为药物的用途。
• TAKAMI, MASAAKI;OKADA, MASAFUMI;TSUDZII, NOBUDZI;XOSOGAI, TAKEHO;OMURA, S+
  作者：TAKAMI, MASAAKI、OKADA, MASAFUMI、TSUDZII, NOBUDZI、XOSOGAI, TAKEHO、OMURA, S+

  DOI：——

  日期：——