bis[2-(2-methoxyethyoxy)ethyl] but-2-ynedioate | 1078574-77-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: bis[2-(2-methoxyethyoxy)ethyl] but-2-ynedioate
• 英文别名: 1,4-bis[2-(2-methoxyethoxy)ethyl] 2-butynedioate；bis[2-(2-methoxyethoxy)ethyl]acetylenedicarboxylate；Bis-[2-(2-methoxyethoxy)ethyl] acetylenedicarboxylate；bis[2-(2-methoxyethoxy)ethyl] but-2-ynedioate
• CAS: 1078574-77-2
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: OLSARKUZKJVWOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±40.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis[2-(2-methoxyethyoxy)ethyl] but-2-ynedioate 在 [,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 氘代丙酮 为溶剂， 以85%的产率得到bis(2-(2-methoxyethoxy)ethyl) maleate
  参考文献：
  名称：

  New Hyperpolarized Contrast Agents for ¹³C-MRI from Para-Hydrogenation of Oligooxyethylenic Alkynes

  摘要：

  Two alkyne derivatives, which contain one and two oligooxyethylenic chains respectively, showed to be good substrates for para-hydrogenation reactions, yielding the corresponding hyperpolarized alkenes in good yields. A suitable theory has been developed to account for the observed results, fully explaining the different para-H-2 induced effects observed upon the para-hydrogenation of symmetrically and asymmetrically substituted alkynes in ALTADENA and PASADENA modes. The oligooxyethylenic substituent provides good water solubility to the para-hydrogenated symmetrical derivative. C-13-MR in vitro images of the latter derivative were obtained both in acetone and in water solutions (130 mM), using the ALTADENA procedure and after application of the field cycling procedure which allows acquisition of an in-phase C-13 carbonyl resonance. The finding that the hydrogenated product is water-soluble in contrast to the parent alkyne which is not allows for the pursuit of a fast phase-transfer separation from the organic solvent, the unreacted substrate, and the catalyst to obtain a "ready-to-use" water solution suitable for further in vivo MRI applications.

  DOI：

  10.1021/ja8059733
• 作为产物：
  描述：

  二乙二醇单甲醚 、 丁炔二酸二甲酯 在 硫酸 作用下， 反应 8.0h， 以30%的产率得到bis[2-(2-methoxyethyoxy)ethyl] but-2-ynedioate
  参考文献：
  名称：

  New Hyperpolarized Contrast Agents for ¹³C-MRI from Para-Hydrogenation of Oligooxyethylenic Alkynes

  摘要：

  Two alkyne derivatives, which contain one and two oligooxyethylenic chains respectively, showed to be good substrates for para-hydrogenation reactions, yielding the corresponding hyperpolarized alkenes in good yields. A suitable theory has been developed to account for the observed results, fully explaining the different para-H-2 induced effects observed upon the para-hydrogenation of symmetrically and asymmetrically substituted alkynes in ALTADENA and PASADENA modes. The oligooxyethylenic substituent provides good water solubility to the para-hydrogenated symmetrical derivative. C-13-MR in vitro images of the latter derivative were obtained both in acetone and in water solutions (130 mM), using the ALTADENA procedure and after application of the field cycling procedure which allows acquisition of an in-phase C-13 carbonyl resonance. The finding that the hydrogenated product is water-soluble in contrast to the parent alkyne which is not allows for the pursuit of a fast phase-transfer separation from the organic solvent, the unreacted substrate, and the catalyst to obtain a "ready-to-use" water solution suitable for further in vivo MRI applications.

  DOI：

  10.1021/ja8059733

文献信息

• Metal-Free Multicomponent Tandem Polymerizations of Alkynes, Amines, and Formaldehyde toward Structure- and Sequence-Controlled Luminescent Polyheterocycles
  作者：Bo Wei、Weizhang Li、Zujin Zhao、Anjun Qin、Rongrong Hu、Ben Zhong Tang

  DOI：10.1021/jacs.6b12767

  日期：2017.4.12

  Sequence-controlled polymers, including biopolymers such as DNA, RNA, and proteins, have attracted much attention recently because of their sequence-dependent functionalities. The development of an efficient synthetic approach for non-natural sequence-controlled polymers is hence of great importance. Multicomponent polymerizations (MCPs) as a powerful and popular synthetic approach for functional polymers with great structural diversity have been demonstrated to be a promising tool for the synthesis of sequence-controlled polymers. In this work, we developed a facile metal-free one-pot multicomponent tandem polymerization (MCTP) of activated internal alkynes, aromatic diamines, and formaldehyde to successfully synthesize structural-regulated and sequence-controlled polyheterocycles with high molecular weights (up to 69 800 g/mol) in high yields (up to 99%). Through such MCTP, polymers with the in situ generated multisubstituted tetrahydropyrimidines or dihydropyrrolones in the backbone and inherent luminescence can be easily obtained with high atom economy and environmental benefit, which is inaccessible by other synthetic approaches.
• Electrospray Mass Spectrometry to Study Combinatorial iClick Reactions and Multiplexed Kinetics of [Ru(N₃)(N∧N)(terpy)]PF₆ with Alkynes of Different Steric and Electronic Demand
  作者：Tristan Zach、Florian Geyer、Benjamin Kiendl、Jan Mößeler、Olivier Nguyen、Thomas Schmidpeter、Patrick Schuster、Christoph Nagel、Ulrich Schatzschneider

  DOI：10.1021/acs.inorgchem.2c03377

  日期：2023.2.20
• Process for the Preparation of Aqueous Solutions of Hyperpolarized Molecules
  申请人：Reineri Francesca

  公开号：US20110178393A1

  公开（公告）日：2011-07-21

  The invention relates to a one-step process for the preparation of aqueous solutions of hyperpolarized molecules in which, in a single step, the said hyperpolarized molecules are separated from the crude solution by means of a fast phase-transfer extraction and isolated in an impurity-free aqueous solution, ready for use in the MRI diagnostic imaging of organs, region or tissues of the human or animal body.
• US8961933B2
  申请人：——

  公开号：US8961933B2

  公开（公告）日：2015-02-24
• New Hyperpolarized Contrast Agents for ¹³C-MRI from Para-Hydrogenation of Oligooxyethylenic Alkynes
  作者：Francesca Reineri、Alessandra Viale、Giovanbattista Giovenzana、Daniela Santelia、Walter Dastrù、Roberto Gobetto、Silvio Aime

  DOI：10.1021/ja8059733

  日期：2008.11.12

  Two alkyne derivatives, which contain one and two oligooxyethylenic chains respectively, showed to be good substrates for para-hydrogenation reactions, yielding the corresponding hyperpolarized alkenes in good yields. A suitable theory has been developed to account for the observed results, fully explaining the different para-H-2 induced effects observed upon the para-hydrogenation of symmetrically and asymmetrically substituted alkynes in ALTADENA and PASADENA modes. The oligooxyethylenic substituent provides good water solubility to the para-hydrogenated symmetrical derivative. C-13-MR in vitro images of the latter derivative were obtained both in acetone and in water solutions (130 mM), using the ALTADENA procedure and after application of the field cycling procedure which allows acquisition of an in-phase C-13 carbonyl resonance. The finding that the hydrogenated product is water-soluble in contrast to the parent alkyne which is not allows for the pursuit of a fast phase-transfer separation from the organic solvent, the unreacted substrate, and the catalyst to obtain a "ready-to-use" water solution suitable for further in vivo MRI applications.