N-[2-(3-氯苯基)乙基]-4-甲基苯磺酰胺 | 194853-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[2-(3-氯苯基)乙基]-4-甲基苯磺酰胺
• 英文名称: N-[2-(3-chlorophenyl)ethyl]-4-methylbenzenesulfonamide
• CAS: 194853-79-7
• 化学式: C₁₅H₁₆ClNO₂S
• mdl: MFCD01185668
• 分子量: 309.817
• InChiKey: DKSZWIFOWPGONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-chloro-α-(phenylthio)acetophenone 、 N-[2-(3-氯苯基)乙基]-4-甲基苯磺酰胺 在 zinc dibromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以54%的产率得到[6-chloro-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1H-isoquinolin-1-yl]-phenylmethanone
  参考文献：
  名称：

  使用Pictet-Spengler环化与α-氯代-α-苯基硫代酮精制1-苯甲酰基四氢异喹啉衍生物。邻甲基紫杉碱的合成

  摘要：

  的反应Ñ -tosyl-β-苯乙胺与α氯代-α-phenylthioketones，改性的Pictet-格勒条件下导致1苯甲酰基和1-新戊酰四氢异喹啉，进行说明。报道了使用该转化作为关键步骤的O-甲基维隐氨酸的合成。

  DOI：

  10.1016/s0040-4039(01)01998-0
• 作为产物：
  描述：

  对甲苯磺酰氯 在 sodium azide 、 二氢吡啶 、 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene 、 4-甲苯硫酚 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.05h， 生成 N-[2-(3-氯苯基)乙基]-4-甲基苯磺酰胺
  参考文献：
  名称：

  Organo‐Photocatalytic Anti‐Markovnikov Hydroamidation of Alkenes with Sulfonyl Azides: A Combined Experimental and Computational Study

  摘要：

  The construction of C(sp3)−N bonds via direct N‐centered radical addition with olefins under benign conditions is a desirable but challenging strategy. Herein, we describe an organo‐photocatalytic approach to achieve anti‐Markovnikov alkene hydroamidation with sulfonyl azides in a highly efficient manner under transition‐metal‐free and mild conditions. A broad range of substrates, including both activated and unactivated alkenes, are suitable for this protocol, providing a convenient and practical method to construct sulfonylamide derivatives. A synergistic experimental and computational mechanistic study suggests that the additive, Hantzsch ester (HE), might undergo a triplet‐triplet energy transfer manner to achieve photosensitization by the organo‐photocatalyst under visible light irradiation. Next, the resulted triplet excited state 3HE* could lead to a homolytic cleavage of C4−H bond, which triggers a straightforward H‐atom transfer (HAT) style in converting sulfonyl azide to the corresponding key amidyl radical. Subsequently, radical addition of the amidyl radical to alkenes followed by HAT from p‐toluenethiol could proceed to afford the desired anti‐Markovnikov hydroamidation product. It is worth noting that mechanistic pathway bifurcation could be possible for this reaction. A feasible radical chain propagation mechanistic pathway is also proposed to rationalize the high efficiency of this reaction.

  DOI：

  10.1002/anie.202406069

文献信息

• ENZYME-CATALYZED ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
  申请人：California Institute of Technology

  公开号：US20160222423A1

  公开（公告）日：2016-08-04

  The present invention provides methods for catalyzing the conversion of an olefin to a compound containing one or more aziridine functional groups using heme enzymes. In certain aspects, the present invention provides a reaction mixture for producing an aziridination product, the reaction mixture comprising of an olefinic substrate, a nitrene precursor, and a heme enzyme. In other certain aspects, the present invention provides a method for producing an aziridination product comprising providing an olefinic substrate, a nitrene precursor, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce an aziridine product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin aziridination reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.

  本发明提供了利用血红素酶催化烯烃转化为含有一个或多个氮杂环丙烷官能团的化合物的方法。在某些方面，本发明提供了用于生产氮杂环丙烷产物的反应混合物，该反应混合物包括烯烃底物、氮烯前体和血红素酶。在其他某些方面，本发明提供了一种生产氮杂环丙烷产物的方法，包括提供烯烃底物、氮烯前体和血红素酶；并将这些组分混合在反应中，以产生氮杂环丙烷产物所需的时间。在其他方面，本发明提供了包括能够在体内和体外进行烯烃氮杂环丙烷化反应的血红素酶及其变体和片段。本发明还提供了表达载体和表达血红素酶的宿主细胞。
• New Syntheses of 1-Benzoyltetrahydroisoquinoline Derivatives Using Polymer-supported Bis(trifluoroacetoxyiodo)benzene
  作者：Ling-Ching Chen、Hsin-Yu Huang、Rei-Sheu Hou、Huey-Min Wang

  DOI：10.3987/com-05-10433

  日期：——

  The reaction of N-benzenesulfonyl-β-phenethylamines with α-benzoyl sulfides using polymer-supported bis(trifluoroacetoxyiodo)benzene (PSBTI) gives moderate to good yields of the corresponding 1-benzoyltetrahydroisoquinoline derivatives.

  使用聚合物负载的双（三氟乙酰氧基碘）苯 (PSBTI) 使 N-苯磺酰基-β-苯乙胺与 α-苯甲酰硫化物反应，得到相应的 1-苯甲酰基四氢异喹啉衍生物的产率适中至良好。
• Development of Photoredox Cross-Electrophile Coupling of Strained Heterocycles with Aryl Bromides Using High-Throughput Experimentation for Library Construction
  作者：Yukiko Mori、Mutsuyo Hayashi、Ryuma Sato、Kuninori Tai、Tsuyoshi Nagase

  DOI：10.1021/acs.orglett.3c01821

  日期：2023.8.4

  cross-coupling reaction of aryl halides with strained aliphatic heterocycles facilitated via a ring-opening reaction. This methodology was found to be applicable to medicinally relevant substrates including Boc-protected strained aliphatic heterocycles and (hetero)aryl bromides and was used for compound library construction via parallel medicinal chemistry. Furthermore, the coupling reactions were shown

  采用微型高通量实验开发了芳基卤化物与张力脂肪族杂环通过开环反应促进的光氧化还原辅助还原交叉偶联反应。该方法被发现适用于医学相关底物，包括 Boc 保护的应变脂肪族杂环和（杂）芳基溴，并用于通过平行药物化学构建化合物库。此外，通过连续流动反应，偶联反应可扩展到克级。还讨论了可能的反应机理。
• Ytterbium Triflate-catalysed Synthesis of Ethyl 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates Using Ethyl Chloro(phenylselanyl)acetate
  作者：Ling-Ching Chen、Huey-Min Wang、Iou-Jiun Kang

  DOI：10.3987/com-03-9799

  日期：——
• Kang, Iou-Jiun; Wang, Huey-Min; Su, Chien-Hsing, Heterocycles, 2002, vol. 57, # 1, p. 1 - 4
  作者：Kang, Iou-Jiun、Wang, Huey-Min、Su, Chien-Hsing、Chen, Ling-Ching

  DOI：——

  日期：——