methyl 2-(5-methoxy-2-methyl-1-(3-(trifluoromethyl)benzoyl)-1H-indol-3-yl)acetate | 942431-85-8

• 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
• 英文名称: methyl 2-(5-methoxy-2-methyl-1-(3-(trifluoromethyl)benzoyl)-1H-indol-3-yl)acetate
• 英文别名: Methyl 2-[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]indol-3-yl]acetate；methyl 2-[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]indol-3-yl]acetate
• CAS: 942431-85-8
• 化学式: C₂₁H₁₈F₃NO₄
• 分子量: 405.373
• InChiKey: MPWSDKXFYPCNAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(5-methoxy-2-methyl-1-(3-(trifluoromethyl)benzoyl)-1H-indol-3-yl)acetate 在 trimethyl-tin hydroxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以90%的产率得到2-(5-甲氧基-2-甲基-1-(4-(三氟甲基)苯甲酰基)-1H-吲哚-3-基)乙酸
  参考文献：
  名称：

  Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up

  摘要：

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.044
• 作为产物：
  描述：

  5-甲氧基-2-甲基-3-吲哚乙酸 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl 2-(5-methoxy-2-methyl-1-(3-(trifluoromethyl)benzoyl)-1H-indol-3-yl)acetate
  参考文献：
  名称：

  Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up

  摘要：

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.044

文献信息

• Metallaphotoredox Perfluoroalkylation of Organobromides
  作者：Xiangbo Zhao、David W. C. MacMillan

  DOI：10.1021/jacs.0c09977

  日期：2020.11.18

  Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via

  Ruppert-Prakash 型试剂（TMSCF3、TMSC2F5 和 TMSC3F7）是容易获得、空气稳定且易于处理的氟代烷基源。在此，我们描述了这些氟烷基亲核试剂与芳基和烷基溴的温和、铜催化交叉偶联，以产生各种三氟甲基、五氟乙基和七氟丙基加合物。这种光介导的转化通过甲硅烷基-自由基介导的卤素原子提取途径进行，这使得各种空间和电子需求可变的有机溴化物的全氟烷基化成为可能。通过几种药物类似物的后期功能化证明了该方法的实用性。
• Persistent organonickel complexes as general platforms for Csp2–Csp3 coupling reactions
  作者：Long P. Dinh、Hunter F. Starbuck、Taylor B. Hamby、Matthew J. LaLama、Cyndi Q. He、Dipannita Kalyani、Christo S. Sevov

  DOI：10.1038/s41557-024-01528-7

  日期：——

  reactions rely on the discovery of unusually persistent organonickel complexes that serve as stoichiometric platforms for C(sp2)–C(sp3) coupling. Aryl, heteroaryl or vinyl complexes of Ni can be inexpensively prepared on a multigram scale by mild electroreduction from the corresponding C(sp2) electrophile. Organonickel complexes can be isolated and stored or telescoped directly to reliably diversify

  构建 C sp 2 –C sp 3键的重要性推动了电化学、光化学和热活化方法的发展，以还原偶联丰富的芳基和烷基亲电子试剂。然而，这些方法仅限于非常特定的底物类别的耦合，并且需要专门的催化剂组和反应装置。在这里，我们展示了将这些无数的策略整合到一组条件中，以实现可靠的烷基芳基偶联，包括那些以前未知的偶联。这些反应依赖于异常持久的有机镍配合物的发现，该配合物可作为 C( sp 2 )–C( sp 3 ) 偶联的化学计量平台。 Ni的芳基、杂芳基或乙烯基配合物可以通过相应的C( sp 2 )亲电子试剂的温和电还原以数克规模廉价地制备。有机镍络合物可以被分离和储存或直接伸缩，以可靠地多样化药物样分子。最后，通过整合可溶性电池化学物质作为氧化还原引发剂，将该过程小型化至微摩尔尺度，从而实现底物多样性的高通量探索。
• Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up
  作者：Andy J. Liedtke、Kwangho Kim、Donald F. Stec、Gary A. Sulikowski、Lawrence J. Marnett

  DOI：10.1016/j.tet.2012.08.044

  日期：2012.12

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.