3,3'-[butane-1,4-diylbis(5-methyl-2,4-dioxopyrimidine-3,1(2H,4H)-diyl)]dipropanoic acid dimethyl ester | 1393681-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,3'-[butane-1,4-diylbis(5-methyl-2,4-dioxopyrimidine-3,1(2H,4H)-diyl)]dipropanoic acid dimethyl ester
• 英文别名: 3,3'-(3,3'-(butane-1,4-diyl)bis(5-methyl-2,4-dioxo-3,4-dihydropyrimidine-3,1(2H)-diyl))dipropanoate (butyl-bis-thymine)；dimethyl 3,3'-(3,3'-(butane-1,4-diyl)bis(5-methyl-2,4-dioxo-3,4-dihydropyrimidine-3,1(2H)-diyl))dipropanoate；dimethyl 3,3′-(butane-1,4-diylbis(5-methyl-2,4-dioxo-3,4-dihydropyrimidine-3,1(2H)-diyl))dipropionate；Butyl-linked bis-thymine propanoate；methyl 3-[3-[4-[3-(3-methoxy-3-oxopropyl)-5-methyl-2,6-dioxopyrimidin-1-yl]butyl]-5-methyl-2,4-dioxopyrimidin-1-yl]propanoate
• CAS: 1393681-53-2
• 化学式: C₂₂H₃₀N₄O₈
• 分子量: 478.502
• InChiKey: CHMQUVJOOLSPOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-[butane-1,4-diylbis(5-methyl-2,4-dioxopyrimidine-3,1(2H,4H)-diyl)]dipropanoic acid dimethyl ester 在 水 、 sodium hydroxide 作用下， 反应 4.0h， 以88%的产率得到3,3'-(3,3'-(butane-1,4-diyl)bis(5-methyl-2,4-dioxo-3,4-dihydropyrimidine-3,1(2H)-diyl))dipropanoic acid
  参考文献：
  名称：

  Photo-responsive self-assemblies based on bio-inspired DNA-base containing bolaamphiphiles

  摘要：

  具有光响应性的胸腺嘧啶插入的双胆超分子/超分子，可以通过紫外辐射将聚集形态从带状结构转变为球形结构。

  DOI：

  10.1039/c4cc08580a
• 作为产物：
  描述：

  生成 3,3'-[butane-1,4-diylbis(5-methyl-2,4-dioxopyrimidine-3,1(2H,4H)-diyl)]dipropanoic acid dimethyl ester
  参考文献：
  名称：

  微乳液中可逆大环化合物的拓扑控制合成

  摘要：

  一种新颖而简单的方法被用来合成可逆的大环化合物。该方法基于捕获微乳液内部具有光动力共价键的分子作为纳米反应器，并将其暴露于紫外线辐射下，以促进立体选择反应，从而定量和选择性地形成环状化合物。所用微乳液液滴的大小在合成可逆大环化合物中起着至关重要的作用。形成的大环化合物能够在较短波长的紫外线照射下还原为单体。

  DOI：

  10.1021/acs.joc.9b00913

文献信息

• [EN] BIS-THYMINE DERIVATIVES AND PHOTO-REVERSIBLE POLYMERS THEREOF<br/>[FR] DÉRIVÉS DE BIS-THYMINE ET LEURS POLYMÈRES PHOTORÉVERSIBLES
  申请人：UNIV MONASH

  公开号：WO2012149604A1

  公开（公告）日：2012-11-08

  The present invention relates to bis-thymine derivatives and processes for their preparation. The present invention also relates to the photoreversible polymerization of the bis-thymine derivatives to form polymers and uses thereof.

  本发明涉及嘧啶二聚体衍生物及其制备方法。本发明还涉及利用嘧啶二聚体衍生物进行光可逆聚合形成聚合物以及其用途。
• The interplay between hydrogen bonding and π-π stacking interactions in the crystal packing of N1-thyminyl derivatives, and implications for the photo-chemical [2π + 2π]-cycloaddition of thyminyl compounds
  作者：Priscilla Johnston、Ekaterina I. Izgorodina、Kei Saito

  DOI：10.1039/c2pp25228g

  日期：2012.12

  The solid-state photo-chemical dimerisation of thyminyl derivatives occurs when two thyminyl units are aligned in such a way that the olefinic moieties are separated by a distance of less than 4.2 Å. When irradiated with >270 nm UV, the thyminyl olefinic groups undergo [2π + 2π]-cycloaddition to form a dimeric cyclobutane derivative. However, the design and execution of [2π + 2π]-cycloaddition reactions can be challenging due to the requirement to produce molecular crystals with the necessary olefinic alignment. In this investigation, the crystallographic and solid-state photo-chemical reactions of six N1-thyminyl derivatives are studied. Only one derivative, thyminyl propanamide (7), was found to undergo [2π + 2π]-cycloaddition in the crystalline state. As such, quantum chemical methods were employed to study the photo-chemical transition states of the derivatives, as well as the strengths of typical intermolecular interactions that were observed in their crystal structures (such as π–π stacking between the thyminyl rings, Watson and Crick style hydrogen bonding and hydrogen bonding between functional groups of N1 substituents). These results were used to rationalise the solid-state photo-reactivity of more complex bis-thyminyl monomers.

  固态光化学二聚反应发生在两个胸苷单元以特定方式排列，使得它们的不饱和键之间的距离小于4.2 Å时。当用波长大于270 nm的紫外线照射时，胸苷的不饱和基团会经历[2π + 2π]环加成反应，形成二聚的环丁烷衍生物。然而，设计和执行[2π + 2π]环加成反应可能具有挑战性，因为需要制备具有必要不饱和键排列的分子晶体。在本研究中，研究了六种N1-胸苷衍生物的晶体学和固态光化学反应。仅发现胸苷丙酰胺（7）在晶体状态下经历[2π + 2π]环加成反应。因此，采用了量子化学方法研究了这些衍生物的光化学过渡态，以及在它们的晶体结构中观察到的典型分子间相互作用的强度（例如胸苷环之间的π–π堆积、沃森-克里克式氢键以及N1取代基功能团之间的氢键）。这些结果被用来合理化更复杂的二胸苷单体的固态光化学反应活性。
• Topologically Controlled Synthesis of Reversible Macrocyclic Compounds in Microemulsions
  作者：Yanallah Alqarni、Toby D. M. Bell、Rico F. Tabor、Kei Saito

  DOI：10.1021/acs.joc.9b00913

  日期：2019.7.5

  reversible macrocyclic compound. This approach is based on capturing molecules with a photodynamic covalent bond inside microemulsions as nanoreactors and exposing them to UV radiation to facilitate a stereoselective reaction to form cyclic compounds quantitatively and selectively. The size of the microemulsion droplets used played a crucial role in synthesizing the reversible macrocyclic compounds. The

  一种新颖而简单的方法被用来合成可逆的大环化合物。该方法基于捕获微乳液内部具有光动力共价键的分子作为纳米反应器，并将其暴露于紫外线辐射下，以促进立体选择反应，从而定量和选择性地形成环状化合物。所用微乳液液滴的大小在合成可逆大环化合物中起着至关重要的作用。形成的大环化合物能够在较短波长的紫外线照射下还原为单体。
• Photo-responsive self-assemblies based on bio-inspired DNA-base containing bolaamphiphiles
  作者：Ahmed S. Al-Shereiqi、Ben J. Boyd、Kei Saito

  DOI：10.1039/c4cc08580a

  日期：——

  Photo-responsive thymine incorporated bolaamphiphiles/superamphiphiles that can transfrom the aggregation morphology into spherical structures from ribbon-like structures by UV irradiation were investigated.

  具有光响应性的胸腺嘧啶插入的双胆超分子/超分子，可以通过紫外辐射将聚集形态从带状结构转变为球形结构。