4-(3'-chlorophenyl)-1,2,4-triazoline-3,5-dione | 138407-59-7

• 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: 4-(3'-chlorophenyl)-1,2,4-triazoline-3,5-dione
• 英文别名: 4-(3-Chlorophenyl)-1,2,4-triazole-3,5-dione
• CAS: 138407-59-7
• 化学式: C₈H₄ClN₃O₂
• 分子量: 209.592
• InChiKey: LFIUHNACDUEFIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±44.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3'-chlorophenyl)-1,2,4-triazoline-3,5-dione 、 以 甲苯 为溶剂， 以46%的产率得到4-(3-Chloro-phenyl)-1-(1-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-[1,2,4]triazolidine-3,5-dione
  参考文献：
  名称：

  一种有效的合成从尿嘧啶和尿苷硫代异抗性的：新型的中性离子核苷。

  摘要：

  [反应：见正文]描述了从尿嘧啶和尿苷衍生出的多种硫代异氰酸酯的合成方法，以及它们的性质和环加成趋势。Anhydro-3-hydrocy-2-phenyl-6-（2'，3'，5'-tri-O-benzoyl-beta-D-rifurfuranosyl）thiazolo [3,2-c] pyrimidine-5（6H）-氢氧化-4-鎓代表一类新型的中离子核苷。

  DOI：

  10.1021/ol990385u
• 作为产物：
  描述：

  4-(3-Chlorophenyl)-urazole 在 calcium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(3'-chlorophenyl)-1,2,4-triazoline-3,5-dione
  参考文献：
  名称：

  乌拉唑的望远镜氧化和环加成获得二氮杂环丁烯

  摘要：

  我们以前访问二氮杂环丁烯支架的方法不允许修改源自 1,2,4-三唑啉-3,5-二酮成分的取代基。我们已经规避了这一挑战，并扩大了对脚手架额外结构多样性的访问。伸缩的乌拉唑氧化和路易斯酸催化的环化提供了 R 3取代的二氮杂环丁烯。次氯酸钙介导的乌拉唑氧化，随后 MgCl 2催化所得三唑啉二酮与硫代炔烃的环化促进了二氮杂环丁烯的形成，该二氮杂环丁烯在源自三唑啉二酮组分的R 3位置带有取代。

  DOI：

  10.1021/acs.joc.2c00280

文献信息

• Diazacyclobutene derivatives and methods of synthesis thereof
  申请人：Clemson University

  公开号：US10875869B1

  公开（公告）日：2020-12-29

  Provided is a compound having the formula: wherein: R1 is selected from the group consisting of H, aliphatic of 1 to 100 carbons and arene comprising up to 100 carbons; R2 is selected from the group consisting of H, aliphatic of 1 to 100 carbons and arene comprising up to 100 carbons; each R3 is independently selected from the group consisting of H, aliphatic of 1 to 100 carbons and arene comprising up to 100 carbons; X is selected from the group consisting of B, O, N, S, Se and P; and n is 1-4 as necessary to complete the valence of X formed by the reaction of a compound of Formula III: and a compound of Formula IV:

  提供的是具有以下结构的化合物：其中：R1从H、含有1至100个碳原子的脂肪族和含有最多100个碳原子的芳香族中选择；R2从H、含有1至100个碳原子的脂肪族和含有最多100个碳原子的芳香族中选择；每个R3独立地从H、含有1至100个碳原子的脂肪族和含有最多100个碳原子的芳香族中选择；X从B、O、N、S、Se和P中选择；n为1-4，以完成由Formula III的化合物和Formula IV的化合物反应形成的X的价。
• Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron–Carbon Bond
  作者：Junxian Yang、Ji-Wei Zhang、Wen Bao、Sheng-Qi Qiu、Shaoyu Li、Shao-Hua Xiang、Jun Song、Junmin Zhang、Bin Tan

  DOI：10.1021/jacs.1c05079

  日期：2021.8.25

  desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the

  通过本文报道的手性磷酸催化去对称化策略，实现了先前难以捉摸的具有 C-B 立体轴的轴向手性 B-芳基-1,2-氮杂硼烷的催化对映选择性构建。3,5-二取代苯酚与重氮二甲酰胺的亲电芳香取代反应可以有效地提供这些轴向手性结构，并具有优异的对映控制。有效的远程立体化学控制是通过手性磷酸和两种底物之间的多个明确定义的 H 键相互作用实现的。同时，1,2-氮杂硼碱中弱酸性的N-H作为H键供体可以显着缩短反应时间。反应的可扩展性和产物中 N-N 键的易裂解进一步证明了该方法的实用性。
• Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles
  作者：Yu-Hang Miao、Zheng-Xu Zhang、Xu-Yi Huang、Yuan-Zhao Hua、Shi-Kun Jia、Xiao Xiao、Min-Can Wang、Li-Ping Xu、Guang-Jian Mei

  DOI：10.1016/j.cclet.2023.108830

  日期：2024.4

  “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between 2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder

  由于偶氮亲二烯体的高亲电子性质，偶氮-Diels-Alder即使不需要催化剂也能快速进行，因此被认为是“点击反应”。这种自发性会引起强烈的背景反应，并对化学家开发催化不对称版本提出了艰巨的挑战。本文报道了 2-乙烯基吲哚和三唑二酮之间的第一个催化不对称脱芳香偶氮-狄尔斯-阿尔德反应。该协议利用脱芳构化的高能垒来避免偶氮-狄尔斯-阿尔德反应的强烈背景反应，从而允许在环境温度下实施预计的反应。已经进行了密度泛函理论计算，以深入了解反应机理和对映选择性的起源。通过使用这种方法，可以很容易地制备出多种四环吲哚衍生物，其产率良好至优异，并且具有优异的非对映和对映选择性（33个实例，产率高达97%，并且>99%，>20:1）。
• Proton, electron, and hydrogen atom transfers from ions, radicals, and radical ions derived from substituted urazoles and triazolinediones
  作者：M. J. Bausch、B. David

  DOI：10.1021/jo00030a017

  日期：1992.2

  In dimethyl sulfoxide (DMSO) solution, pK(a)'s for the monoanion and radical derived from 4-phenylurazole have been determined to be 24.8 and 9 +/- 2, respectively. The acidity constant for the 4-phenylurazolyl radical has been determined via a thermochemical cycle that incorporates proton- and electron-transfer data for ions and radicals derived from 4-phenylurazole and 4-phenyl-1,2,4-triazoline-3,5-dione. The acidity data indicate that (a) the 4-phenylurazolide monanion is ca. 14 pK(a) units less acidic than 4-phenylurazole (pK(a) = 11.0) and (b) the 4-phenylurazolyl radical is slightly more acidic than 4-phenylurazole. The estimated pK(a) for the 4-phenylurazolyl radical is reasonable in light of the reversible cyclic voltammetric reduction observed for 4-phenyl-1,2,4-triazoline-3,5-dione. Also in DMSO solution, the homolytic strengths of hydrazyl N-H bonds present in 4-phenylurazole, as well as for the monoanion and radical derived from 4-phenylurazole, are within 3 kcal/mol of each other. These data suggest that the 4-phenylurazolyl radical disproportionation reaction (forming 4-phenylurazole and 4-phenyl-1,2,4-triazoline-3,5-dione) is approximately thermoneutral. Similar relationships are found for ions, radicals, and radical ions derived from 4-methylurazole and 4-methyl-1,2,4-triazoline-3,5-dione.
• A New Addition-Rearrangement of [1,4]Thiazine-2-thiones with Aryl-1,2,4-triazoline-3,5-diones
  作者：Tomás Torroba、Nuria García、Pedro Fuertes、Susana Barriga、Ana G. Neo、Daniel Miguel

  DOI：10.3987/com-02-9699

  日期：——