2-(4-(dimethylamino)but-2-yn-1-yl)isoindoline-1,3-dione | 105773-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(4-(dimethylamino)but-2-yn-1-yl)isoindoline-1,3-dione
• 英文别名: 2-(4-(dimethylamino)but-2-ynyl)isoindoline-1,3-dione；N-phthalimido-N',N'-dimethylbutin-2-yl-1,4-diamine；1-(N,N-dimethyl)amino-4-phthalimido-2-butyne；N-(4-dimetilamino-2-butinil)ftalimide；N-(4-dimethylamino-but-2-ynyl)-phthalimide；N-(4-Dimethylamino-2-butinyl)-phthalimid；2-[4-(dimethylamino)but-2-ynyl]isoindole-1,3-dione
• CAS: 105773-89-5
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: HUWODKUYIUANIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-(dimethylamino)but-2-yn-1-yl)isoindoline-1,3-dione 生成 N,N-dimethyl-2-butyne-1,4-diamine
  参考文献：
  名称：

  Ferrand; Maffrand; Eloy, European Journal of Medicinal Chemistry, 1975, vol. 10, # 6, p. 549 - 556

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium phtalimide 在 copper(l) chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(4-(dimethylamino)but-2-yn-1-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  OMEGA-AMINOALKYLAMIDES OF (R)-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF THE CHEMOTAXIS OF POLYMORPHONUCLEATE AND MONONUCLEATE CELLS

  摘要：

  公开号：

  EP1366018B1

文献信息

• Inhibition of bovine plasma amine oxidase by 1,4-diamino-2-butenes and -2-butynes
  作者：Heung-Bae Jeon、Younghee Lee、Chunhua Qiao、He Huang、Lawrence M Sayre

  DOI：10.1016/s0968-0896(03)00521-2

  日期：2003.10

  The finding that the bis-primary amines 1,4-diamino-2-butyne (a known potent inhibitor of diamine oxidases) and Z-2-chloro-1,4-diamino-2-butene are potent inactivators of BPAO is suggestive of unexpected similarities between plasma amine oxidase and the diamine oxidases and implies that it may be unwise to attempt to develop selective inhibitors of diamine oxidase using a diamine construct.

  牛血浆胺氧化酶（BPAO）先前已显示被炔丙基胺和2-氯烯丙基胺不可逆地抑制。这两种化合物的1,4-二胺版本在此处显示为高效灭活剂，IC50值接近20 microM。在每种情况下，单-N-烷基化或N，N-二烷基化都会大大降低失活能力，而单-N-酰基衍生物也是较弱的抑制剂，酶活性可以恢复。双伯胺1,4-二氨基-2-丁炔（一种已知的二胺氧化酶的有效抑制剂）和Z-2-氯-1,4-二氨基-2-丁烯是BPAO的有效灭活剂的发现提示：血浆胺氧化酶和二胺氧化酶之间出乎意料的相似性，这意味着尝试使用二胺构建物开发选择性的二胺氧化酶抑制剂可能是不明智的。
• Practical synthesis of silyl-protected and functionalized propargylamines using nanostructured Ag/TiO2 and Pt/TiO2 as active recyclable catalysts
  作者：Yasser M. A. Mohamed、Hossam A. El Nazer、Eirik Johansson Solum

  DOI：10.1007/s11696-018-0604-6

  日期：2019.2

  Herein we report the use of Ag/TiO2 and Pt/TiO2 nanocatalysts to promote the synthesis of a series of silyl-protected and functionalized propargylamine derivatives through alkyne–amine–aldehyde (A3) coupling under microwave condition using water as solvent in short reaction times with high yielding production. A comparative study between the two catalysts was also demonstrated to prove that Pt/TiO2 nanocomposite has higher potential effect for propargylamines synthesis more than Ag/TiO2. The main features of the investigated method for propargylamines synthesis were easy handling, low catalyst loading as well as the feasibility of catalyst recyclability. The prepared compounds are potentially beneficial with possible pharmacological and biological properties, which that could be used in several disciplines including medicinal and agricultural applications.

  在此，我们报告了使用 Ag/TiO2 和 Pt/TiO2 纳米催化剂在微波条件下，以水为溶剂，通过炔-胺-醛（A3）偶联促进一系列硅烷保护和功能化丙炔胺衍生物的合成，反应时间短，产率高。对两种催化剂的比较研究也证明，Pt/TiO2 纳米复合材料比 Ag/TiO2 在合成丙炔胺方面具有更高的潜在效果。所研究的丙炔胺合成方法的主要特点是操作简便、催化剂负载量低以及催化剂可回收利用。所制备的化合物具有潜在的药理和生物特性，可用于多个学科，包括医药和农业应用。
• Propargylamine Synthesis by Copper-Catalyzed Oxidative Coupling of Alkynes and Tertiary Amine <i>N</i>-Oxides
  作者：Zhanwei Xu、Xiaoqiang Yu、Xiujuan Feng、Ming Bao

  DOI：10.1021/jo201059h

  日期：2011.8.19

  An efficient method for synthesizing N,N-dimethylpropargylamines is described. The synthesis exploited the Cu(II)-catalyzed oxidative alkynylation reaction of trimethylamine N-oxides with alkynes in the absence of external oxidant. Both aromatic and aliphatic alkynes were utilized to achieve the corresponding products in moderate to excellent yields. The reaction conditions tolerated ester, hydroxy

  描述了一种合成N，N-二甲基炔丙基胺的有效方法。在没有外部氧化剂的情况下，该合成利用了Cu（II）催化的三甲胺N-氧化物与炔烃的氧化炔基化反应。芳族和脂族炔均用于以中等至优异的产率获得相应的产物。反应条件容许酯，羟基和醛基。
• Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C–H versus C–C cleavage in TMEDA
  作者：Qi Shen、Lei Zhang、Yu-Ren Zhou、Jian-Xin Li

  DOI：10.1016/j.tetlet.2013.09.118

  日期：2013.12

  Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand. (C) 2013 Elsevier Ltd. All rights reserved.
• Vitali; Impicciatore; Plazzi, Farmaco, Edizione Scientifica, 1986, vol. 41, # 6, p. 483 - 498
  作者：Vitali、Impicciatore、Plazzi、Bordi、Morini

  DOI：——

  日期：——