2,6-bis[(3-dimethylamino)prop-1-one-2-ene]pyridine | 331942-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis[(3-dimethylamino)prop-1-one-2-ene]pyridine
• 英文别名: 2,6-Bis(3-dimethylamino-1-oxoprop-2-enyl)pyridine；bisenaminone；(E)-3-(dimethylamino)-1-[6-[(E)-3-(dimethylamino)prop-2-enoyl]-2-pyridyl]prop-2-en-1-one；(E)-3-(dimethylamino)-1-[6-[(E)-3-(dimethylamino)prop-2-enoyl]pyridin-2-yl]prop-2-en-1-one
• CAS: 331942-32-6
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: SGWRTZRVJHNLMG-GFULKKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis[(3-dimethylamino)prop-1-one-2-ene]pyridine 在 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 C-{4-[6-(2-aminomethylpyrimidin-4-yl)pyridin-2-yl]pyrimidin-2-yl}methylamine
  参考文献：
  名称：

  响应氨基酸的存在而实现较大的颜色变化：一种对天冬氨酸具有选择性的分子传感组件。

  摘要：

  DOI：

  10.1021/ja011905v
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 、 Bredereck 试剂 反应 0.25h， 以89%的产率得到2,6-bis[(3-dimethylamino)prop-1-one-2-ene]pyridine
  参考文献：
  名称：

  Molecular Architecture. 2.¹ Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

  摘要：

  Methods are described for the synthesis of a series of functionalized derivatives of 9-butyl-1,2,3,4,5,6,7,8-octahydroacridine (9), a building block for several types of highly preorganized host compounds. A key intermediate is 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one (23), which can also be used in the syntheses of torands and hydrogen-bonding hexagonal lattice receptors. A tridentate cleft (20), consisting of 2,2';6',2 "-terpyridine imbedded in a heptacyclic framework, and a corresponding pentadentate diketone (6) were synthesized from 9 in five and seven steps, respectively. The picrate extraction method was used to estimate the solution stabilities of alkali metal complexes of heptacyclic terpyridyls 6 and 20, which was also compared with a flexible terpyridyl (37). Alkali metal complexes of both heptacyclic terpyridyls showed relatively high K-s values, but low size selectivity. Pentadentate host 6 binds Na+ and K+ more strongly than do most hexadentate crown ethers; flexible tridentate analogue 37 failed to extract alkali metal picrates into chloroform. The complexation abilities of 6 and 20 are attributed to enforced orientation of functional group dipoles toward the center of the molecular cleft. Sodium and potassium picrate complexes of pentadentate cleft 6 were synthesized (1:1 stoichiometry), and a 2:1 complex of calcium triflate (6(2) . Ca(CF3SO3)(2)) was also prepared.

  DOI：

  10.1021/jo9720041

文献信息

• Building off the back of chelators: Synthesis of 3,3″-bis(4-methylphenyl)-2,2′:6′,2″-terpyridine
  作者：Andrew C. Benniston

  DOI：10.1016/s0040-4039(97)10167-8

  日期：1997.11

  Using an adaptation of the Jameson method for the synthesis of 2,2′ :6′,2″-terpyridine (terpy), a ditolyl-functionalised ligand has been prepared in which the substituted groups are located in the highly unusual 3,3″ position. The new ligand represents an attempt to develop terpy-based systems with di-functionality that emerges from the ‘back side’ of the chelator.

  使用詹姆森方法的一种改进方法合成2,2'：6'，2''-吡啶（叔丁基），制备了二糖基官能化的配体，其中取代基位于高度不寻常的3,3''中位置。新的配体代表了开发具有双功能的基于叔丁基的系统的尝试，这种系统从螯合剂的“背面”出现。
• The Reaction of Enaminones with Carboxamidines: A Convenient Route for the Synthesis of Polyaza Heterocycles
  作者：E. Bejan、H. Aït Haddou、J. C. Daran、G. G. A. Balavoine

  DOI：10.1055/s-1996-4330

  日期：1996.8

  A simple and efficient synthetic method to polyaza heterocyclic structures containing 1,3-pyrimidine units has been developed. It is based on the reaction of the enaminones such as 5, 7 and 9 with the appropriate carboxamidines under basic conditions. By this procedure several new polyaza heterocycles have been prepared in good yields.

  我们开发出了一种简单高效的合成方法，用于合成含有 1,3 嘧啶单元的多氮杂环结构。该方法基于 5、7 和 9 等烯酰胺酮与适当的羧酰胺在碱性条件下的反应。通过这种方法，我们以良好的收率制备出了几种新的多氮杂环。
• Synthesis of Chiral Molecules Containing Pyridine and 1,3-Pyrimidine Units: Potential Building Blocks for Helicating and Caging Ligands
  作者：Frédéric Pezet、Lucie Routaboul、Jean-Claude Daran、Isabelle Sasaki、Hassan Aı̈t-Haddou、Gilbert G.A Balavoine

  DOI：10.1016/s0040-4020(00)00795-x

  日期：2000.10

  A simple and efficient method for the synthesis of new chiral polyaza heterocylic structures containing pyridines and 1,3-pyrimidine units has been developed. It is based on the reaction of the appropriate enaminones with optically pure carboxamidine derived from the commercially available (R)-(−)-myrtenal.

  已经开发了一种简单有效的方法来合成新的含有吡啶和1,3-嘧啶单元的手性聚氮杂杂环结构。它基于适当的烯胺酮与衍生自可商购获得的（R）-（-）-myrtenal的光学纯羧box的反应。
• Bis(pyridine)enaminone as a Precursor for the Synthesis of Bis(azoles) and Bis(azine) Utilizing Recent Economic Green Chemistry Technology: The Q-Tube System
  作者：Khadijah M. Al-Zaydi、Tamer S. Saleh、Norah F. Alqahtani、Meaad S. Bagazi

  DOI：10.3390/molecules28052355

  日期：——

  We reported herein efficient economic high-pressure synthesis procedures for the synthesis of bis(azoles) and bis(azines) by utilizing the bis(enaminone) intermediate. Bis(enaminone) reacted with hydrazine hydrate, hydroxylamine hydrochloride, guanidine hydrochloride, urea, thiourea, and malononitrile to form the desired bis azines and bis azoles. A combination of elemental analyses and spectral data

  我们在此报道了利用双（烯胺酮）中间体合成双（唑）和双（嗪）的高效经济高压合成程序。双（烯胺酮）与水合肼、盐酸羟胺、盐酸胍、尿素、硫脲和丙二腈反应形成所需的双嗪和双唑。使用元素分析和光谱数据的组合来确认产品的结构。与传统加热相比，高压Q-Tube方法在短时间内促进反应并提供高产率。
• Di(2-aryl hydrozonopropanal) arene derivatives
  申请人：King Abdulaziz University

  公开号：US10981872B1

  公开（公告）日：2021-04-20

  Di (2-Aryl Hydrazonopropanal) arene derivatives are provided. The compounds exhibit high levels of toxicity against e.g. human colon cancer cells and are used to treat cancer.

  提供了二（2-芳基肼丙醛）炔衍生物。这些化合物对人类结肠癌细胞等具有很强的毒性，可用于治疗癌症。