3-(4-氨基苯基)-2-丙炔-1-醇 | 253167-82-7

• 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: 3-(4-氨基苯基)-2-丙炔-1-醇
• 英文名称: 3-(4-aminophenyl)-2-propyn-1-ol
• 英文别名: 3-(4-aminophenyl)prop-2-yn-1-ol
• CAS: 253167-82-7
• 化学式: C₉H₉NO
• mdl: MFCD00168841
• 分子量: 147.177
• InChiKey: XANNFDGZXZOZCG-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  320.2±27.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-氨基苯基)-2-丙炔-1-醇 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以63%的产率得到4-氨基苯丙醇
  参考文献：
  名称：

  Optimized N-phenyl-N′-(2-chloroethyl)ureas as potential antineoplastic agents: Synthesis and growth inhibition activity

  摘要：

  In our ongoing research program aimed at the optimization of microtubule-self-assembly disrupting agents, we have prepared three series of phenylurea analogues (CEU), derived from N-(3-omega-hydroxyalkyl or 4-omega-hydroxyalkyl or 3-omega-hydroxyalkynyl)phenyl-N'-(2-chloroethyl)ureas. Most compounds exhibit potent growth inhibitory activity on human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7 tumor cell lines, with a GI(50) ranging from 250 nM to 8 mu M. Among these new molecules, three CEUs exhibit GI(50) in the nanomolar range. They are more potent by approximately an order of magnitude than previously described CEU analogues. As such, they are attractive hit compounds for the development of potent new alkylating antitubulin drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.048
• 作为产物：
  描述：

  聚合甲醛 、 4-乙炔基苯胺 在 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以77%的产率得到3-(4-氨基苯基)-2-丙炔-1-醇
  参考文献：
  名称：

  铜（我）碘化催化从末端炔初级炔丙醇的合成†

  摘要：

  使用CuI作为催化剂，多聚甲醛作为甲醛源，已经开发出一种高效，实用的伯炔丙醇合成方法。该反应在温和的反应条件下进行，以各种末端炔烃提供所需产物，收率良好至优异。

  DOI：

  10.1039/c4ra12719f

文献信息

• 3-ARYL PROPIOLONITRILE COMPOUNDS FOR THIOL LABELING
  申请人：UNIVERSITE DE STRASBOURG

  公开号：US20160145199A1

  公开（公告）日：2016-05-26

  The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.

  本发明涉及一种将含硫醇基团的化合物用3-芳基丙炔腈化合物标记的方法，以及用标记基团取代的3-芳基丙炔腈化合物和特定的3-芳基丙炔腈连接剂。
• Synthesis of 3-Substituted Furans by Hydroformylation
  作者：Perli Nanayakkara、Howard Alper

  DOI：10.1002/adsc.200505238

  日期：2006.3

  for the synthesis of 3-substituted furans by the hydroformylation of substituted propargylic alcohols is described using rhodium acetate and triphenylphosphine in dichloromethane. The hydroformylation reaction proceeds in a regioselective manner under mild reaction conditions. This novel methodology is versatile and can be applied to the synthesis of a variety of 3-aryl-substituted furans.

  描述了一种使用乙酸铑和三苯基膦在二氯甲烷中通过取代的炔丙基醇的加氢甲酰化合成3-取代的呋喃的简单新颖的方法。加氢甲酰化反应在温和的反应条件下以区域选择性的方式进行。这种新颖的方法学用途广泛，可用于合成各种3-芳基取代的呋喃。
• New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes
  作者：Philippe Reutenauer、Milan Kivala、Peter D. Jarowski、Corinne Boudon、Jean-Paul Gisselbrecht、Maurice Gross、François Diederich

  DOI：10.1039/b714731g

  日期：——

  Donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative were prepared by a [2 + 2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) to anilino-substituted cyanoalkynes, followed by retro-electrocyclisation; they feature intense bathochromically-shifted intramolecular charge-transfer bands and undergo their

  通过四氰基乙烯的[2 + 2]环加成反应制备供体取代的1,1,2,4,4-戊酰基丁-1,3-二烯和环己2,5-二烯-1,4-二亚甲基膨胀的衍生物（TCNE）或7,7,8,8-四氰基喹二甲烷（TCNQ）生成苯胺基取代的氰基炔烃，然后进行逆电环化；它们具有强烈的红移色移的分子内电荷转移带，并以类似于TCNE和TCNQ报道的电势经历其第一单电子还原。
• MAPN: First-in-Class Reagent for Kinetically Resolved Thiol-to-Thiol Conjugation
  作者：Oleksandr Koniev、Sergii Kolodych、Zoljargal Baatarkhuu、Johann Stojko、Jitka Eberova、Jean-Yves Bonnefoy、Sarah Cianférani、Alain Van Dorsselaer、Alain Wagner

  DOI：10.1021/acs.bioconjchem.5b00440

  日期：2015.9.16

  Thiols are among the most frequently used functional groups in the field of bioconjugation. While there exists a variety of heterobifunctional reagents that allow for coupling thiols to other functions (e.g., amines, carboxylic acids), there is no specific reagent for creating heteroconjugates using two different thiols. In response to the ever-increasing demand for bioconjugation tools, we have developed p-(maleimide)-phenylpropionitrile (MAPN)—an efficient reagent for kinetically resolved thiol-to-thiol coupling. In a comparative study with its closest commercially available analogue, p-phenylenedimaleimide, MAPN has shown substantial advantages for the preparation of thiol–thiol heteroconjugates. Namely, an antibody–drug conjugate (ADC) with mertansine (DM1), conjugated to the cysteine residues of Trastuzumab, was prepared for the first time.

  硫醇是生物共轭领域中最常用的官能团之一。虽然存在多种允许将硫醇与其他官能团（例如胺、羧酸）偶联的异双功能试剂，但没有特定的试剂用于使用两种不同的硫醇创建杂合物。为了满足对生物偶联工具不断增长的需求，我们开发了对（马来酰亚胺）-苯基丙腈（MAPN）——一种用于动力学解析硫醇与硫醇偶联的有效试剂。在与其最接近的市售类似物对苯二甲酰亚胺的比较研究中，MAPN 在制备硫醇-硫醇杂合物方面显示出巨大的优势。即，首次制备了与曲妥珠单抗的半胱氨酸残基缀合的美坦辛（DM1）的抗体药物缀合物（ADC）。
• Cellulose/silica supported Schiff base Pd(II) catalyst for copper-free Sonogashira cross-coupling
  作者：Pravin S. Pharande、Pradeep M. Mhaldar、Mayuri V. Patil、Suraj A. Sonawane、Shrikrishna T. Salunke、Dattaprasad M. Pore

  DOI：10.1007/s11164-023-05186-1

  日期：2024.2

  Sonogashira cross-coupling. Varity of functionalized diary acetylene derivatives have been achieved with admirable yields from coupling of aryl halides and phenyl acetylenes. The XRD, SEM and TGA analysis of recycled catalyst revealed remarkable catalytic activity. The proposed approach exhibits remarkable merits such as impressively low catalyst loading (0.009 mol%), elevated turnover numbers (up to 10

  摘要 在本研究中，以纤维素为载体，设计并合成了纤维素/二氧化硅负载的希夫碱Pd(II)催化剂，缩写为Cell/SiO 2 -Sal-Pd(II)。采用FTIR、XRD、TGA、SEM、EDS、BET/BJH等先进技术对催化剂进行了综合表征。根据EDX分析，发现钯的负载量为0.017mol%。TEM 分析显示催化剂的粒径约为 70 nm。Cell/SiO 2 -Sal-Pd(II)的催化效率在 Sonogashira 交叉偶联的背景下进行了彻底的审查。通过芳基卤化物和苯乙炔的偶联，已经获得了各种官能化二芳基乙炔衍生物，且收率令人赞叹。回收催化剂的 XRD、SEM 和 TGA 分析显示出显着的催化活性。所提出的方法具有显着的优点，例如令人印象深刻的低催化剂负载量（0.009 mol%）、较高的周转数（高达 10,556）、值得称赞的周转频率（高达 3519）、出色的热稳定性（高达 356.75