N,1-dimethyl-1H-indole-3-carboxamide | 85729-22-2

• 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: N,1-dimethyl-1H-indole-3-carboxamide
• 英文别名: 1,N-dimethylindole-3-carboxamide；N,1-dimethylindole-3-carboxamid；N,1-dimethylindole-3-carboxamide
• CAS: 85729-22-2
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD04126330
• 分子量: 188.229
• InChiKey: OHXYWSIWHXTWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,1-dimethyl-1H-indole-3-carboxamide 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(2-(4-fluorophenyl)-2-oxoethyl)-2,4,5-trimethyl-4,5-dihydro-1H-pyrido[4,3-b]indole-1,3(2H)-dione
  参考文献：
  名称：

  Photoredox Catalyzed Radical Cascade Aroylation (Sulfonylation)/Cyclization Enables Access to Fused Indolo-pyridones

  摘要：

  DOI：

  10.1021/acs.joc.1c02335
• 作为产物：
  描述：

  1-甲基吲哚-3-甲酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 N,1-dimethyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  Efficient Synthesis of N-Methylamides and Amines via 4-(Alkylamino)benzyl-N-methylamine as a New Protecting Group

  摘要：

  4-(Alkylamino)benzyl-N-methylamine is a good protecting group for the synthesis of N-methylamides and amines. The N-debenzylation of N-methylamides and amines can be carried out selectively and efficiently under condition using trifluoroacetic acid (TFA).

  DOI：

  10.3987/com-13-12747

文献信息

• Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
  作者：Ting-Yu Zhang、Chang Liu、Chao Chen、Jian-Xin Liu、Heng-Ye Xiang、Wei Jiang、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.7b03580

  日期：2018.1.5

  An efficient and environmentally benign Cu-mediated method was developed for direct cascade C–H/N–H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C–H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline

  开发了一种高效且环境友好的铜介导的方法，用于直接级联C–H / N–H环化，以构建多杂环吲哚并喹啉支架。该方法突出了在有机合成中将惰性C–H键转变为通用官能团的新兴策略，并为有效合成吲哚[3,2- c ]和[2,3- c ]喹啉生物碱提供了新的通用方法。
• Hydrogenation of amides catalyzed by a combined catalytic system of a Ru complex with a zinc salt
  作者：Yusuke Kita、Takafumi Higuchi、Kazushi Mashima

  DOI：10.1039/c4cc04481a

  日期：——

  Hydrogenation of unactivated amides has been achieved by using the combined catalytic system of a ruthenium catalyst with a zinc salt.

  未活化酰胺的氢化已通过使用钌催化剂与锌盐的联合催化系统实现。
• Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles
  作者：Veeranjaneyulu Lanke、Kiran R. Bettadapur、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.orglett.6b02698

  日期：2016.11.4

  A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between

  公开了通过改变酮指导基团的性质实现在吲哚骨架中C-2和C-4位置之间的位点选择性的新模式。甲基酮作为导向基团仅提供C-2烯基化产物，而三氟甲基酮改变了对C-4的选择性，表明该导向基团的电子性质控制着5元和6元金属环之间的不寻常选择。 。对其他羰基衍生的导向基团的筛选显示强和弱的导向基团表现出相反的选择性。实验控制和氘代实验为提出的机制提供了支持。
• Cobalt-Catalyzed CH Arylations with Weakly-Coordinating Amides and Tetrazoles: Expedient Route to Angiotensin-II-Receptor Blockers
  作者：Jie Li、Lutz Ackermann

  DOI：10.1002/chem.201500552

  日期：2015.4.7

  Cobalt‐catalyzed CH arylations enabled the synthesis of biaryl tetrazoles, which are key structural motifs in antihypertensive angiotensin‐II‐receptor blockers. Thus, weakly‐coordinating benzamides were employed for step‐economical CH arylations with ample scope. Further, a low‐valent NHC complex enabled first cobalt‐catalyzed CH functionalization by tetrazole assistance.

  钴催化的CH芳基化能够合成联芳基四唑，这是降压血管紧张素II受体阻滞剂中的关键结构基序。因此，弱配位的苯甲酰胺被用于步长经济的CH芳基化，具有足够的范围。此外，低价的NHC配合物可通过四唑的辅助作用首先使钴催化CH官能化。
• Rh^III-Catalyzed Synthesis of Cyclopenta[<i>b</i>]carbazoles via Cascade C–H/C–C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group
  作者：Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.9b03969

  日期：2020.1.3

  Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[b]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional

  已开发出铑催化的级联CH / CC裂解和3-酰胺取代的吲哚与二炔的环化反应，以构建环戊[b]咔唑。在该方案中已公开了一种策略酰胺，它作为一种新型的无痕导向基团，以及通过Friedel-Crafts-retro反应的CC键裂解。该方法显示出广泛的底物范围并耐受各种官能团，从而以良好或高收率提供了咔唑衍生物。