乙基3-甲基-3-壬基-2-环氧乙烷羧酸酯 | 89438-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 乙基3-甲基-3-壬基-2-环氧乙烷羧酸酯
• 中文别名: 2-丁基-1,2-二氢-3H-吲唑-3-酮
• 英文名称: 2-butyl-1,2-dihydro-3H-indazol-3-one
• 英文别名: 2-butyl-2,3-dihydro-1H-indazol-3-one；N²-n-butylindazolone；2-butyl-1H-indazol-3(2H)-one；2-butyl-1H-indazol-3-one
• CAS: 89438-55-1
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD13192283
• 分子量: 190.245
• InChiKey: OXPAKOUDBFTPRL-UHFFFAOYSA-N

物化性质

• 沸点：
  305.0±25.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  5-[4’-(溴甲基)-[1,1’-联苯]-2-基]-2-(三苯基甲基)-2H-四氮唑 、 乙基3-甲基-3-壬基-2-环氧乙烷羧酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以19%的产率得到2-butyl-2,3-dihydro-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]-1H-indazol-3-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of AT₁ Angiotensin II Receptor Antagonists Based on the Pyrazolo[3,4-b]pyridine and Related Heteroaromatic Bicyclic Systems

  摘要：

  Novel AT(1) receptor antagonists bearing the pyrazolo[3,4-b]pyridine bicyclic heteroaromatic system (or structurally related moieties) were designed and synthesized as the final step of a large program devoted to the development of new anti hypertensive agents and to the understanding of the molecular basis of their pharmacodynamic and pharmacokinetic properties. The preliminary pharmacological characterization revealed nanomolar AT(1) receptor affinity for several compounds of the series and a potent antagonistic activity in isolated rabbit aortic strip functional assay for 7c and 8a. These results stimulated the study of the biopharmaceutical properties of some selected compounds, which were found to be characterized by a permeability from medium to high. Remarkably, the least permeable 7c showed both permeability and oral bioavailability (80%) higher than losartan, but its terminal half-life was shorter. These results suggest that the permeability is not a limiting factor in the pharmacokinetics of these AT(1) receptor antagonists.

  DOI：

  10.1021/jm7011563
• 作为产物：
  描述：

  N-butyl-2-nitrobenzamide 在 四羟基二硼 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以84%的产率得到乙基3-甲基-3-壬基-2-环氧乙烷羧酸酯
  参考文献：
  名称：

  A B₂(OH)₄-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library

  摘要：

  Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B-2(OH)(4)-mediated reductive N-N bond formation is developed. This strategy features mild conditions, no request for a metal catalyst, and a wide scope for both aliphatic and aromatic amines. Meanwhile, this method was further successfully applied on DNA to construct indazolone cores for a DNA-encoded library. This will enable the production of a very attractive indazolone-cored library from simple amines and scaffolds, which will provide considerable diversity.

  DOI：

  10.1021/acs.orglett.0c02032

文献信息

• Photocatalyst‐free Synthesis of Indazolones under CO ₂ Atmosphere
  作者：Tianbao Yang、Huiai Lu、Renhua Qiu、Ling Hong、Shuang‐Feng Yin、Nobuaki Kambe

  DOI：10.1002/asia.201900306

  日期：2019.5.2

  A convenient photocatalyst‐free method for the synthesis of redox‐active 1,2‐dihydro‐3H‐indazol‐3‐one derivatives from (2‐nitroaryl)methanol and amines was developed. The reaction proceeded efficiently at room temperature by irradiation of UV light under CO2 atmosphere (1.0 atm, flow) without any photocatalysts or additives. This mild, operationally simple method shows wide functional tolerance. The

  开发了一种简便的无光催化剂方法，可从（2-硝基芳基）甲醇和胺类合成氧化还原活性的1,2-二氢-3 H-吲唑-3-酮衍生物。在室温下，通过在无任何光催化剂或添加剂的情况下，通过在CO 2气氛（1.0 atm，流量）下照射紫外线，使反应有效地进行。这种温和，操作简单的方法显示出广泛的功能公差。由CO 2和胺原位形成的氨基甲酸酯被认为是该反应的关键。已发现通过本方法合成的某些化合物具有较高的抗癌活性，可降低癌细胞系HeLa，MCF-7和U87的活力。
• Davis–Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route to <i>N</i>-Aryl 2<i>H</i>-Indazoles
  作者：Niklas Kraemer、Clarabella J. Li、Jie S. Zhu、Julio M. Larach、Ka Yi Tsui、Dean J. Tantillo、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/acs.orglett.9b02213

  日期：2019.8.2

  The Davis–Beirut reaction provides access to 2H-indazoles from aromatic nitro compounds. However, N-aryl targets have been traditionally challenging to access due to competitive alternate reaction pathways. Previously, the key nitroso imine intermediate was generated under alkaline conditions, but as reported here, the photochemistry of o-nitrobenzyl alcohols empowered Brønsted acid catalyzed conditions

  Davis-Beirut 反应可以从芳香硝基化合物中获得 2 H-吲唑。然而，由于竞争性的替代反应途径， N-芳基靶标传统上很难获得。以前，关键的亚硝基亚胺中间体是在碱性条件下生成的，但正如本文所报道的，邻硝基苯甲醇的光化学赋予了布朗斯台德酸催化条件来接近N-芳基目标。苯胺和烷基胺在优化条件下会产生不同的结果；使用量子化学计算研究了所提出的机制。
• 一种二氧化碳促进和无光催化剂光诱导合成吲唑啉酮类化合物制备方法
  申请人：湖南大学

  公开号：CN109734666B

  公开（公告）日：2023-03-28

  本发明以喹啉2‑硝基苯甲醇类化合物、胺类衍生物为原料，以廉价、易得的普通灯泡作为反应的光源，以二氧化碳为促进剂，以常用的有机溶剂作反应溶剂，反应在一定温度下反应一定时间，高产率、高选择性地得到吲唑啉酮类化合物，并且在克级放大反应中得到很高的产率。
• Rapid and halide compatible synthesis of 2-<i>N</i>-substituted indazolone derivatives <i>via</i> photochemical cyclization in aqueous media
  作者：Hui-Jun Nie、An-Di Guo、Hai-Xia Lin、Xiao-Hua Chen

  DOI：10.1039/c9ra02466b

  日期：——

  Indazolone derivatives exhibit a wide range of biological and pharmaceutical properties. We report a rapid and efficient approach to provide structurally diverse 2-N-substituted indazolones via photochemical cyclization in aqueous media at room temperature. This straightforward protocol is halide compatible for the synthesis of halogenated indazolones bearing a broad scope of substrates, which suggests

  吲唑酮衍生物表现出广泛的生物学和药学特性。我们报告了一种快速有效的方法，通过在室温下在水性介质中的光化学环化来提供结构多样的 2 - N-取代吲唑酮。这种简单的方案与卤化物相容，可用于合成具有广泛底物的卤代吲唑酮，这为药物化学提供了一条非常重要的新途径。
• Photochemical Preparation of 1,2-Dihydro-3<i>H</i>-indazol-3-ones in Aqueous Solvent at Room Temperature
  作者：Jie S. Zhu、Niklas Kraemer、Clarabella J. Li、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/acs.joc.8b02356

  日期：2018.12.21

  involve its isolation via chromatography and/or formation under harsh conditions. Herein, this intermediate was photochemically generated in situ from o-nitrobenzyl alcohols in a mild, efficient manner for the construction of 1,2-dihydro-3 H-indazol-3-ones using an aqueous solvent at room temperature. This convenient reaction offers several advantages over reported methods. The commercially available photoreactor

  邻硝基苯甲醛是一种反应性中间体，可用于合成氮杂环。以前使用邻亚硝基苯甲醛的策略涉及通过色谱分离和/或在苛刻条件下形成。在此，该中间体以温和，有效的方式从邻硝基苄基醇原位光化学生成，用于在室温下使用水性溶剂构建1,2-二氢-3 H-吲唑-3-酮。与报道的方法相比，这种方便的反应具有多个优点。市售的光反应器使用3×18 W灯泡，可在365 nm以上发出宽广的发射光。