2-iodo-3-methyl-N-phenylbenzamide | 1379820-76-4

• 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: 2-iodo-3-methyl-N-phenylbenzamide
• CAS: 1379820-76-4
• 化学式: C₁₄H₁₂INO
• 分子量: 337.16
• InChiKey: BBAUEUVTCTTWGB-UHFFFAOYSA-N

物化性质

• 沸点：
  349.9±35.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-iodo-3-methyl-N-phenylbenzamide 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以7%的产率得到7-methyl-2-phenyl-1,2-benzisothiazol-3-one
  参考文献：
  名称：

  Structure‐Activity Studies Reveal Scope for Optimisation of Ebselen‐Type Inhibition of SARS‐CoV‐2 Main Protease

  摘要：

  AbstractThe reactive organoselenium compound ebselen is being investigated for treatment of coronavirus disease 2019 (COVID‐19) and other diseases. We report structure‐activity studies on sulfur analogues of ebselen with the Severe Acute Respiratory Syndrome coronavirus 2 (SARS‐CoV‐2) main protease (Mpro), employing turnover and protein‐observed mass spectrometry‐based assays. The results reveal scope for optimisation of ebselen/ebselen derivative‐ mediated inhibition of Mpro, particularly with respect to improved selectivity.

  DOI：

  10.1002/cmdc.202100582
• 作为产物：
  描述：

  2-碘-3-甲基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-iodo-3-methyl-N-phenylbenzamide
  参考文献：
  名称：

  Structure‐Activity Studies Reveal Scope for Optimisation of Ebselen‐Type Inhibition of SARS‐CoV‐2 Main Protease

  摘要：

  AbstractThe reactive organoselenium compound ebselen is being investigated for treatment of coronavirus disease 2019 (COVID‐19) and other diseases. We report structure‐activity studies on sulfur analogues of ebselen with the Severe Acute Respiratory Syndrome coronavirus 2 (SARS‐CoV‐2) main protease (Mpro), employing turnover and protein‐observed mass spectrometry‐based assays. The results reveal scope for optimisation of ebselen/ebselen derivative‐ mediated inhibition of Mpro, particularly with respect to improved selectivity.

  DOI：

  10.1002/cmdc.202100582

文献信息

• KO^<i>t</i>Bu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones
  作者：Bhagat Singh Bhakuni、Amit Kumar、Shah Jaimin Balkrishna、Javeed Ahmed Sheikh、Sanjit Konar、Sangit Kumar

  DOI：10.1021/ol301077y

  日期：2012.6.1

  Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon–carbon bond forming reaction gives direct access to various biaryl lactams containing six- and seven-membered rings chemoselectively. Carbon–carbon coupling seems to proceed by the generation

  在叔丁醇钾和催化量的1,10-菲咯啉或AIBN的存在下，由2-卤代苯甲酰胺合成了取代的菲啶酮和二苯并a庚酮。这种新的碳-碳键形成反应可直接接近具有化学选择性的六元和七元环的各种联芳基内酰胺。碳-碳偶合似乎是通过酰胺环中自由基的产生而进行的，从而导致苯胺的CH芳基化。
• A base-free copper-assisted synthesis of <i>C</i>₂-symmetric spirotelluranes and biaryls based on divergent stoichiometry of Na₂Te
  作者：Monojit Batabyal、Saket Jain、Aditya Upadhyay、Saravanan Raju、Sangit Kumar

  DOI：10.1039/d2cc02181a

  日期：——

  methodology has been developed for the preparation of biologically important C2-symmetric spirodiaza, benzyloxy and benzoxytelluranes from 2-bromo-N-aryl benzamides, benzyl alcohols, and benzoic acids by using the tellurium dianion (Te2−) under base-free conditions. Furthermore, C–C coupled biaryl 1,1′-diamides have been prepared by using an excess of Na2Te under the same reaction conditions. The synthesized

  已经开发了一种一锅法 Cu( I ) 辅助合成方法，用于通过使用碲双阴离子从 2-溴-N-芳基苯甲酰胺、苯甲醇和苯甲酸制备具有生物学重要意义的C 2 -对称螺二氮杂、苯甲氧基和苯甲氧基碲烷。 (Te 2- ) 在无碱条件下。此外，在相同的反应条件下，通过使用过量的 Na 2 Te 制备了 C-C 偶联联芳基 1,1'-二酰胺。合成的螺二氮杂碲烷可作为还原 H 2 O 2和硝基-迈克尔反应的有效催化剂。
• Organo-cyanamides: convenient reagents for catalytic amidation of carboxylic acids
  作者：Li-Jing Li、Zhong-Qiang Zhou、Zi-Kui Liu、Yuan-Yuan He、Feng-Cheng Jia、Xiao-Qiang Hu

  DOI：10.1039/d2cc05826j

  日期：——

  An unprecedented DMAP-catalysed amidation of aryl and alkyl carboxylic acids with organo-cyanamides has been developed. Unlike the use of N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as an electrophilic cyanating reagent, an unusual desulfonylation/decyanation reaction model has been disclosed for the first time. Remarkable features of this reaction include readily available substrates, simple

  已经开发出一种前所未有的 DMAP 催化的芳基和烷基羧酸与有机氰胺的酰胺化反应。与使用N-氰基-N-苯基-对甲基苯磺酰胺 (NCTS) 作为亲电氰化试剂不同，首次公开了一种不寻常的脱磺酰化/脱氰反应模型。该反应的显着特点包括容易获得的底物、简单的操作和广泛的范围，能够有效合成结构多样的酰胺。该协议的合成效用通过生物活性羧酸的后期酰胺化和放大反应得到证明。
• Copper-Catalyzed Sulfonylation/Cyclization of Pent-4-ynamides toward Sulfonyl-Functionalized Pyrrol-2-ones
  作者：Danhua Wu、Menglu Jiang、Juan-Juan Wang、Wei Yu

  DOI：10.1021/acs.orglett.3c00441

  日期：2023.3.31

  A domino sulfonylation/intramolecular C–N coupling/dehydrogenation reaction was realized between pent-4-ynamides and sulfonyl chlorides by catalysis of Cu(acac)2 and 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthalene. The reaction provides a convenient approach to sulfonyl-functionalized pyrrol-2-ones. This method can also be applied to the synthesis of 3-alkylidene isoindolinones from 2-ethynyl-benzamides

  在 Cu(acac) 2和 2,2'-双(二苯基磷酰基)-1,1'-联萘的催化下，pent-4-ynamides 和磺酰氯之间实现了多米诺磺酰化/分子内 C-N 偶联/脱氢反应。该反应为磺酰基功能化的吡咯-2-酮提供了一种简便的方法。该方法也可用于从 2-乙炔基-苯甲酰胺合成 3-亚烷基异吲哚啉酮。
• Atroposelective Synthesis of Axially Chiral Styrenes by Platinum‐ Catalyzed Stereoselective Hydrosilylation of Internal Alkynes
  作者：Qimin Wu、Qi Zhang、Shuxin Yin、Aijun Lin、Shang Gao、Hequan Yao

  DOI：10.1002/anie.202305518

  日期：2023.7.24

  A platinum-catalyzed atroposelective hydrosilylation of unactivated internal alkynes has been developed. Various styrene-type atropisomers with open-chained olefins were obtained with high stereo- and enantioselectivity.

  已开发出一种铂催化的未活化内部炔烃的间质选择性氢化硅烷化反应。获得了具有高立体选择性和对映选择性的各种具有开链烯烃的苯乙烯型阻转异构体。