N-(4-methoxyphenylsulfonyl)aziridine | 25860-10-0

• 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: N-(4-methoxyphenylsulfonyl)aziridine
• 英文别名: 1-((4-methoxyphenyl)sulfonyl)aziridine；N-<4-Methoxy-benzolsulfonyl>-aziridin；1-(4-methoxy-benzenesulfonyl)-aziridine；1-(4-Methoxyphenyl)sulfonylaziridine；1-(4-methoxyphenyl)sulfonylaziridine
• CAS: 25860-10-0
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: HKRLNAVXOGZDGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenylsulfonyl)aziridine 在 lithium hydroxide 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 66.0h， 生成 1-[2'-(4-methoxyphenylsulfonamino)ethyl]-4,7,10-tris-[(4'-carboxy)-1'-carboxybutyl]-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  基于可逆分子内磺酰胺连接的大环钆和铕配合物中弛豫和发光的 pH 依赖性调节

  摘要：

  已经制备了一系列大环 Eu、Gd 和 Tb 复合物，其中 β-芳基磺酰胺氮的分子内连接呈现 pH 依赖性，导致镧系元素中心的水合状态 q 发生变化。在基于 DO3A 的复合物中，芳基磺酰胺部分中 p 取代基的变化决定了表观质子化常数 log K(MLH)，-CF(3)、-Me 和 -OMe 取代基的值为 5.7、6.4 和 6.7 ， 分别。引入三个 β-羧基烷基取代基、α 到三个环氮，可抑制添加蛋白质对结合水的置换，并抑制内源性阴离子（乳酸、HCO(3)(-)）的分子间结合。对 Eu 配合物形式和强度的 pH 依赖性的测量表明，分子内羧酸盐配位是竞争性发生的。这可以通过提高磺酰胺氮上的电子密度或通过将螯合环从 7--8 扩大来减少。pH 范围 8--5 中弛豫度变化的放大发生在蛋白质结合上，并且在 pH 值 7.4--6.8 范围内，[Gd.3a]（298 K，65.6 MHz）在 50

  DOI：

  10.1021/ja0103647
• 作为产物：
  描述：

  对甲氧基苯磺酰氯 在 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 N-(4-methoxyphenylsulfonyl)aziridine
  参考文献：
  名称：

  Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace

  摘要：

  Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).

  DOI：

  10.1016/j.bmc.2019.115142

文献信息

• Synthesis of indolines <i>via</i> a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides
  作者：Ce Liu、Yujie Liang、Nian Zheng、Bo-Sheng Zhang、Yuan Feng、Siwei Bi、Yong-Min Liang

  DOI：10.1039/c8cc01062e

  日期：——

  A Pd- and norbornene-catalyzed domino procedure has been developed to synthesize indoline compounds. This reaction provides efficient access to indolines by employing aryl iodides with aziridines as new electrophiles. The transformation is scalable and tolerates a range of functional groups.

  已开发出钯和降​​冰片烯催化的多米诺骨牌合成合成吲哚化合物的方法。通过使用芳基碘化物和氮丙啶作为新的亲电子试剂，该反应提供了有效的二氢吲哚途径。转换是可伸缩的，并且可以容纳一系列功能组。
• Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines
  作者：Ashfaq Ahmad、Himangsu Sekhar Dutta、Mohit Kumar、Raziullah、Manoj Kumar Gangwar、Dipankar Koley

  DOI：10.1021/acs.orglett.2c00120

  日期：2022.4.22

  A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was also tolerated in the presence of various external additives. Control experiments suggested that the C–H cleavage step is

  已经开发了一种钯催化的定向基团辅助脂肪族氮丙啶与吲哚、二氢吲哚、四氢喹啉和苯胺的交叉偶联，以提供相应的 β-芳基乙胺衍生物。底物范围非常笼统，在各种外部添加剂存在的情况下，该方案也可以接受。对照实验表明 C-H 裂解步骤是速率决定步骤。
• Copper‐Catalyzed Heterocyclic Recombination of Aziridine and Diazetidine for the Synthesis of Imidazolidine**
  作者：Daiki Higuchi、Satoshi Matsubara、Hiroki Kadowaki、Daisuke Tanaka、Kei Murakami

  DOI：10.1002/chem.202301071

  日期：2023.8

  goal in organic synthesis. Herein, the Cu-catalyzed synthesis of imidazolidine through heterocyclic recombination between aziridine and diazetidine is presented. The scope is sufficiently broad to form various imidazolidines, since the reaction conditions are suitable for many functional groups.Copper-Catalyzed Heterocyclic Recombination of Aziridine and Diazetidine for the Synthesis of Imidazolidine

  发现金属新的催化应用仍然是有机合成的一个重要目标。在此，提出了通过氮丙啶和二氮杂环丁烷之间的杂环重组，铜催化合成咪唑烷。由于反应条件适合许多官能团，其范围足够广泛，可以形成各种咪唑烷。铜催化氮丙啶和二氮杂环丁烷的杂环重组用于合成咪唑烷（Murakami 等人）
• Development of Macrocyclic Mn(II)−Bispyridine Complexes as pH‐Responsive Magnetic Resonance Imaging Contrast Agents
  作者：Xiaojuan Shen、Yan Pan、Guohai Liang

  DOI：10.1002/ejic.202200786

  日期：——

  efficient response to pH stimuli, and easy modulation characteristics were synthetized in this study. These complexes are considered ideal candidates for use as acidic microenvironment-specific MRI contrast agents.

  本研究合成了具有良好动力学惰性、对 pH 刺激快速有效响应以及易于调节特性的大环 Mn(II)-双吡啶配合物。这些复合物被认为是用作酸性微环境特异性 MRI 造影剂的理想候选者。
• Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace
  作者：Jens Frackenpohl、Linn Schneider、Luka J.B. Decker、Jan Dittgen、Franz Fenkl、Christian Fischer、Jana Franke、Joerg Freigang、Rahel Getachew、Susana M. Gonzalez Fernandez-Nino、Hendrik Helmke、Martin J. Hills、Sabine Hohmann、Jochen Kleemann、Karoline Kurowski、Gudrun Lange、Peter Luemmen、Nicole Meyering、Fabien Poree、Dirk Schmutzler、Sebastian Wrede

  DOI：10.1016/j.bmc.2019.115142

  日期：2019.12

  Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).