tert-butyl N-(2-formylphenyl)-N-methyl-carbamate | 1290035-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-(2-formylphenyl)-N-methyl-carbamate
• 英文别名: Tert-butyl (2-formylphenyl)(methyl)carbamate；tert-butyl N-(2-formylphenyl)-N-methylcarbamate
• CAS: 1290035-27-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: ZAIFMUUYRQESDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.9±25.0 °C(Predicted)
• 密度：
  1.127±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：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(2-formylphenyl)-N-methyl-carbamate 在 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [2-(2,2-dibromovinyl)phenyl]methylamine
  参考文献：
  名称：

  Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles

  摘要：

  A novel synthesis of 2-halo-3-carboxyindoles from 2-(2,2-dihalovinyl)anilines was discovered. Reaction conditions and substrate applicability were studied. Optimally, the reaction takes only minutes when these substrates are heated in DMSO at 120 degrees C in the presence of cesium carbonate. However, the reaction is robust and takes place at a wide range of temperatures, is tolerant of aqueous reaction conditions, and can be performed in a variety of polar solvent/carbonate base combinations where the limiting factor is base solubility. A wide range of substituents is tolerated on the 2-(2,2-dihalovinyl)anilines, and yields are generally high, requiring only acidic aqueous work-up to obtain pure products. No catalyst is required for the transformation. The mechanism is believed to involve initial formation of an alkynyl bromide intermediate followed by ring closure and carbon dioxide trapping, leading to product formation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.037
• 作为产物：
  描述：

  (2-甲基氨基苯基)-甲醇 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 tert-butyl N-(2-formylphenyl)-N-methyl-carbamate
  参考文献：
  名称：

  Organocatalytic Route to Dihydrocoumarins and Dihydroquinolinones in All Stereochemical Configurations

  摘要：

  A straightforward stereodivergent route to dihydrocoumarins and dihydroquinolinones based on cinchona alkaloid catalyzed addition reactions of monothiomalonates (MTMs) to functionalized nitroolefins followed by deprotection and chemoselective cyclization has been developed. The synthesis proceeds under mild conditions and yields heterocycles with adjacent quaternary and tertiary stereogenic centers in very high yields and stereoselectivities. Moreover, full control over the relative and absolute configuration is achieved by the use of (pseudo)enantiomeric catalysts and the difference in reactivity of thioester versus oxoester moieties.

  DOI：

  10.1021/ol502697s

文献信息

• Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals
  作者：Alexander S. Karns、Monalisa Goswami、Bas de Bruin

  DOI：10.1002/chem.201704626

  日期：2018.4.6

  a cobalt(III)-carbene radical intermediate. This methodology employs the use of inexpensive commercially available reagents and allows for the transformation of easily derivatized benzaldehyde-derived precursors to functionalized indoline products. This transformation takes advantage of the known propensity of radicals to undergo rapid intramolecular 1,5-hydrogen atom transfer (1,5-HAT) to form more

  我们报道了一种通过钴(III)-卡宾自由基中间体从邻氨基苯亚甲基N-甲苯磺酰腙合成二氢吲哚的新方法。该方法采用廉价的市售试剂，并允许将容易衍生的苯甲醛衍生前体转化为功能化二氢吲哚产物。这种转化利用自由基进行快速分子内 1,5-氢原子转移 (1,5-HAT) 的已知倾向，形成更稳定的自由基中间体。使用密度泛函理论的计算研究发现 1,5-HAT 和随后的激进回弹位移的势垒非常低，为所提出的机制提供了支持。我们探索了各种氮取代基的影响，并强调了自由基中间体充分共振稳定对于转化成功的重要性。此外，我们评估了苯胺环上取代基的空间和电子效应。该转化是第一个报道的由钴(III)-卡宾自由基前体合成含氮杂环的例子。
• Stereoselective Amine Addition to Six-Membered Cyclic Nitronates Promoted by Silyl Triflate
  作者：Andrey A. Mikhaylov、Alexander D. Dilman、Yulia A. Khomutova、Dmitry E. Arkhipov、Alexander A. Korlyukov、Sema L. Ioffe

  DOI：10.1002/ejoc.201300511

  日期：2013.9

  N‐Silylamines add to six‐membered nitronates with high diastereoselectivity. The reaction follows an original mechanism in which thermodynamic control plays the key role.

  N-甲硅烷基胺会以非对映异构体高选择性地添加到六元硝酸盐中。该反应遵循原始机制，其中热力学控制起着关键作用。
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  申请人：ALIGOS THERAPEUTICS INC

  公开号：WO2021252491A1

  公开（公告）日：2021-12-16

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating coronavirus, Picomavirus and Norovims infections with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

  本文提供了式（I）的化合物或其药用盐，包括包含本文描述的化合物（包括本文描述的化合物的药用盐）的药物组合物以及合成这些化合物的方法。本文还提供了使用式（I）的化合物或其药用盐治疗冠状病毒、皮科病毒和诺如病毒感染的方法。
• ANTI-VIRAL COMPOUNDS
  申请人：Aligos Therapeutics, Inc.

  公开号：US20220009903A1

  公开（公告）日：2022-01-13

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
• [EN] COVALENT EGFR INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS COVALENTS D'EGFR ET LEURS MÉTHODES D'UTILISATION
  申请人：[en]DANA-FARBER CANCER INSTITUTE, INC.

  公开号：WO2023069959A1

  公开（公告）日：2023-04-27

  The disclosure relates to compounds that act as inhibitors of epidermal growth factor receptor (EGFR); pharmaceutical compositions comprising the compounds; and methods of treating or preventing kinase-mediated disorders, including cancer and other proliferation diseases.