5-iodo-N¹-phenyluracil | 905854-82-2

• 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: 5-iodo-N¹-phenyluracil
• 英文别名: 1-phenyl-5-iodouracil；5-iodo-1-phenyluracil；5-Iodo-1-phenylpyrimidine-2,4-dione
• CAS: 905854-82-2
• 化学式: C₁₀H₇IN₂O₂
• 分子量: 314.082
• InChiKey: JMELUSFYVXNSDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-iodo-N¹-phenyluracil 在 吡啶 、 正丁基锂 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.5h， 生成
  参考文献：
  名称：

  具有尿嘧啶氢键功能的乙二硫基四硫富瓦烯衍生物的二维网络及其四乙胺基喹啉甲烷配合物的通道结构

  摘要：

  设计并合成具有N 1-丁基尿嘧啶或N 1-苯基尿嘧啶部分的乙二硫四硫富富烯烯（EDT-TTF）衍生物，作为新的氢键电子给体分子，目的是将多个S···S相互作用引入所组成的氢键结构中TTF-nucleobase系统的。在EDT-TTF衍生物的晶体中，通过π··π，多个S···S相互作用和互补的双氢键形成二维片层结构。在具有分离柱的EDT-TTF- N 1-丁基尿嘧啶二聚体的四氰基喹二甲烷（TCNQ）电荷转移复合物中，电子供体分子的层结构是通过非共价相互作用而构建的。这尿嘧啶部分的正丁基用于分隔供体层之间的空间，从而形成通道结构。无序的TCNQ分子位于通道的微孔空间中。TCNQ复合物在单晶中表现出高电导率（σrt = 2.1 S cm - 1）。

  DOI：

  10.1021/jo060748l
• 作为产物：
  描述：

  1-苯基尿嘧啶 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到5-iodo-N¹-phenyluracil
  参考文献：
  名称：

  具有尿嘧啶氢键功能的乙二硫基四硫富瓦烯衍生物的二维网络及其四乙胺基喹啉甲烷配合物的通道结构

  摘要：

  设计并合成具有N 1-丁基尿嘧啶或N 1-苯基尿嘧啶部分的乙二硫四硫富富烯烯（EDT-TTF）衍生物，作为新的氢键电子给体分子，目的是将多个S···S相互作用引入所组成的氢键结构中TTF-nucleobase系统的。在EDT-TTF衍生物的晶体中，通过π··π，多个S···S相互作用和互补的双氢键形成二维片层结构。在具有分离柱的EDT-TTF- N 1-丁基尿嘧啶二聚体的四氰基喹二甲烷（TCNQ）电荷转移复合物中，电子供体分子的层结构是通过非共价相互作用而构建的。这尿嘧啶部分的正丁基用于分隔供体层之间的空间，从而形成通道结构。无序的TCNQ分子位于通道的微孔空间中。TCNQ复合物在单晶中表现出高电导率（σrt = 2.1 S cm - 1）。

  DOI：

  10.1021/jo060748l

文献信息

• Development of Organic Conductors with Self-Assembled Architectures of Biomolecules: Synthesis and Crystal Structures of Nucleobase-Functionalized Tetrathiafulvalene Derivatives
  作者：Tsuyoshi Murata、Eigo Miyazaki、Suguru Maki、Yoshikazu Umemoto、Makoto Ohmoto、Kazuhiro Nakasuji、Yasushi Morita

  DOI：10.1246/bcsj.20120102

  日期：2012.9.15

  Supramolecular assemblies and charge-transfer complexes of new nucleobase-functionalized tetrathiafulvalene (TTF) derivatives were investigated. Stille-type cross-coupling reaction between tributylstannylated TTF and iodinated nucleobase derivatives yielded mono- and bisnucleobase-substituted TTF derivatives. The electrochemical measurements revealed that the uracil- and cytosine-substituted derivatives possessed strong electron-donating abilities comparable to that of pristine TTF, and the electron-deficient features of adenine and guanine caused high potential shifts of the oxidation waves. In the solution-state electronic spectra, the intramolecular charge-transfer absorption bands were observed at a low-energy region. In the crystal structures, the donor molecules constructed supramolecular polymers by the complementary hydrogen-bonds inherent in nucleobases; a one-dimensional zigzag chain in the adenine-substituted derivative and a linear chain in the bis(uracil)-substituted derivative. The tetracyanoquinodimethane complexes of uracil- and cytosine-substituted derivatives possessed a mixed valence state exhibiting high conductivities (room-temperature conductivities = 10−2–10−1 S cm−1). In the cyananilic acid complexes, cytosine- and adenine-substituted TTF acted as electron-donors and proton-acceptors to yield simultaneous charge- and proton-transfer complexes.

  研究了新型核苷碱功能化的四硫富瓦烯（TTF）衍生物的超分子聚集体和电荷转移复合物。通过斯蒂尔反应，三正丁基锡化的TTF与碘化核苷碱衍生物之间进行了交叉偶联反应，产生了单核苷碱和双核苷碱取代的TTF衍生物。电化学测量表明，取代有尿嘧啶和胞嘧啶的衍生物具有强的电子给体能力， comparable 于纯净的TTF，而腺嘌呤和鸟嘌呤的电子缺乏特征导致了氧化波的高电位移。在溶液态的电子光谱中，观察到了低能量区域的分子内电荷转移吸收带。在晶体结构中，供体分子通过核苷碱固有的互补氢键构建了超分子聚合物；腺嘌呤取代的衍生物形成了一维之字形链，而二尿嘧啶取代的衍生物形成了一条线性链。取代有尿嘧啶和胞嘧啶的四氰基奎烯和二烯复合物具有混合价态，表现出高电导率（室温电导率 = 10−2–10−1 S cm−1）。在氰苯基酸复合物中，胞嘧啶和腺嘌呤取代的TTF作为电子供体和质子受体，形成了同时进行电荷和质子转移的复合物。
• Redox-active tubular frameworks with TTF: self-assemblies by complementary hydrogen-bonds and π-stacks of TTF-phenyluracil
  作者：Tsuyoshi Murata、Suguru Maki、Makoto Ohmoto、Eigo Miyazaki、Yoshikazu Umemoto、Kazuhiro Nakasuji、Yasushi Morita

  DOI：10.1039/c1ce05794d

  日期：——

  Tubular frameworks of a tetrathiafulvalene (TTF) based electron-donor with a N1-phenyluracil moiety were constructed by strong self-assembling abilities. The uracil moiety formed the reversed Watson–Crick type hydrogen-bond pair. The TTF moiety exhibited C–H⋯X hydrogen-bonds, S⋯S interactions, and uniform π-stack. The phenyl group formed a herring-bone array by the edge-to-face interaction. These multiple intermolecular interactions established channels of ca. 4 × 8 Å. The cavities were filled with crystalline solvent molecules (tetrahydrofuran and pyridine), which were fixed on the framework by the C–H⋯X hydrogen-bonds.

  基于四硫富瓦烯（TTF）的电子供体与N1-苯基尿嘧啶部分的管状框架通过强自组装能力构建而成。尿嘧啶部分形成了反向的沃森-克里克型氢键对。TTF部分表现出C–H···X氢键、S···S相互作用以及均匀的π-堆叠。苯基通过边缘对面相互作用形成了鱼骨阵列。这些多重分子间相互作用建立了约4 × 8 Å的通道。腔体被结晶溶剂分子（四氢呋喃和吡啶）填充，这些溶剂分子通过C–H···X氢键固定在框架上。
• Nucleobase-Functionalized 1,6-Dithiapyrene-Type Electron-Donors: Supramolecular Assemblies by Complementary Hydrogen-Bonds and π-Stacks
  作者：Tsuyoshi Murata、Eigo Miyazaki、Kazuhiro Nakasuji、Yasushi Morita

  DOI：10.1021/cg301414s

  日期：2012.11.7

  Synthesis, crystal structures and redox properties Of 1,6-dithiapyrene (DTPY)-type electron donors functionalized with nucleobases (uracil, cytosine and adenine) were investigated. The electrochemical measurements showed that the uracil-substituted derivatives were slightly stronger electron-donors than DTPY, and the cytosine- and adenine-substitution caused a slight weakening of the electron-donating ability. In the crystal structures, DTPY-nucleobases constructed multidimensional assemblies by complementary hydrogen-bonds on the nucleobase moieties and pi-stacks and S center dot center dot center dot S interactions on the DTPY skeleton. The uracil derivative formed two kinds of hydrogen-bonded pairs with different H-bonding modes (Watson-Crick and reverse Watson-Crick types), both of which were further linked through pi-stacks on the DTPY skeleton to construct one-dimensional alternating columns. In the CH2Cl2 solvated crystal, the uracil derivative built up a two-dimensional pi-layer by the complementary hydrogen bonds and pi-stacks In the cytosine derivative, the complementary hydrogen bonded pair assembled by the pi-stacks and S center dot center dot center dot S interactions of the DTPY skeleton constructed a two-dimensional network The adenine derivative formed a channel structure by the one-dimensional pi-stack of complementary hydrogen-bonded pairs, where crystalline water molecules with a ladder-like hydrogen-bonded chain were included. Charge-transfer complexes of DTPY-nucleobases with tetracyanoquinodimethane possessed a neutral ground state and exhibited semiconductive behaviors with room temperature conductivities of 10(-6) to 10(-7) S cm(-1).