3-amino-O-(2-butynyl)-phenol | 519157-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-amino-O-(2-butynyl)-phenol
• 英文别名: 3-But-2-ynoxyaniline
• CAS: 519157-19-8
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: GUXAWXLAMRLTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 3-amino-O-(2-butynyl)-phenol 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以88%的产率得到(3-But-2-ynyloxy-phenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization

  摘要：

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.05.003
• 作为产物：
  描述：

  3-羟基苯基氨基甲酸叔丁酯 在 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 3-amino-O-(2-butynyl)-phenol
  参考文献：
  名称：

  具有多键配体的高效铂 (IV) 络合物靶向线粒体以克服顺铂耐药性

  摘要：

  顺铂类化合物的疗效和耐药性是目前非常棘手的问题。本研究报道了一系列含有多键配体的铂（IV）化合物，其表现出比顺铂更好的肿瘤细胞抑制活性以及抗增殖和抗转移活性。间位取代的化合物2和5特别出色。进一步研究表明化合物2和5具有适当的还原潜能，在细胞摄取、活性氧反应、细胞凋亡和DNA损伤相关基因的上调、耐药细胞活性等方面均明显优于顺铂。标题化合物在体内表现出比顺铂更好的抗肿瘤潜力和更少的副作用。本研究将多键配体引入顺铂中形成标题化合物，不仅增强了它们的吸收并克服了耐药性，而且还展示了靶向线粒体和抑制肿瘤细胞解毒的潜力。

  DOI：

  10.1016/j.ejmech.2023.115235

文献信息

• 一类具有抗肺癌作用的化合物及其制备方法和应用
  申请人：重庆文理学院

  公开号：CN114940692A

  公开（公告）日：2022-08-26

  本发明公开了一类具有抗肺癌作用的化合物及其制备方法和应用，该化合物将含有多重键(双键或三键)的配体引入顺铂形成前药，改善顺铂的药物吸收，同时发挥顺铂和多重键配体的协同作用，增强药物治疗肺癌的效果，部分化合物对顺铂耐药A549细胞的抑制能力明显高于药物顺铂。
• Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation
  作者：Stefan J. Pastine、So Won Youn、Dalibor Sames

  DOI：10.1021/ol034177k

  日期：2003.4.1

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.
• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.