2-氟-5-碘嘧啶 | 697300-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-氟-5-碘嘧啶
• 英文名称: 2-fluoro-5-iodopyrimidine
• CAS: 697300-79-1
• 化学式: C₄H₂FIN₂
• 分子量: 223.976
• InChiKey: IQFADBWJBWUPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1,3-dioxoisoindolin-2-yl benzoylalaninate 、 2-氟-5-碘嘧啶 在 锰 、 nickel(II) tetrafluoroborate hexahydrate 、 C₃₄H₅₀N₄ 作用下， 以 四氢呋喃 为溶剂， 以54 %的产率得到(R)-N-(1-(2-fluoropyrimidin-5-yl)ethyl)benzamide
  参考文献：
  名称：

  镍催化 α-氨基酸 NHP 酯不对称脱羧芳基化生成手性苄胺

  摘要：

  已经建立了镍催化的 NHP 酯通过还原交叉偶联的不对称脱羧基反应。利用氨基酸酯的 NHP 作为自由基前体提供了一种新的方案，其中可以获得结构多样的手性苄胺。该方法具有优异的催化效率、高对映选择性控制、温和的条件和良好的官能团耐受性，从而能够实现生物活性分子和药物的后期修饰。

  DOI：

  10.1021/acs.orglett.3c02431
• 作为产物：
  描述：

  2-氨基-5-碘嘧啶, 在 吡啶 、 氢氟酸 、 sodium nitrite 作用下， 反应 1.5h， 以72%的产率得到2-氟-5-碘嘧啶
  参考文献：
  名称：

  5-Substituted Derivatives of 6-Halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography

  摘要：

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.

  DOI：

  10.1021/jm030432v

文献信息

• Discovery of 2-(4-sulfonamidophenyl)-indole 3-carboxamides as potent and selective inhibitors with broad hepatitis C virus genotype activity targeting HCV NS4B
  作者：Nanjing Zhang、Anthony Turpoff、Xiaoyan Zhang、Song Huang、Yalei Liu、Neil Almstead、F. George Njoroge、Zhengxian Gu、Jason Graci、Stephen P. Jung、John Pichardo、Joseph Colacino、Fred Lahser、Paul Ingravallo、Marla Weetall、Amin Nomeir、Gary M. Karp

  DOI：10.1016/j.bmcl.2015.11.065

  日期：2016.1

  A novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides was identified and optimized for activity against the HCV genotype 1b replicon resulting in compounds with potent and selective activity. Further evaluation of this series demonstrated potent activity across HCV genotypes 1a, 2a and 3a. Compound 4z had reduced activity against HCV genotype 1b replicons containing single mutations in the NS4B coding sequence (F98C and V105M) indicating that NS4B is the target. This novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides serves as a promising starting point for a pan-genotype HCV discovery program. (C) 2015 Elsevier Ltd. All rights reserved.
• Simplifying Access to Targeted Protein Degraders via Nickel Electrocatalytic Cross‐Coupling
  作者：Philipp Neigenfind、Luca Massaro、Áron Péter、Andrew P. Degnan、Megan A. Emmanuel、Martins S. Oderinde、Chi He、David Peters、Tamara El‐Hayek Ewing、Yu Kawamata、Phil S. Baran

  DOI：10.1002/anie.202319856

  日期：2024.4.15

  C−C linked glutarimide‐containing structures with direct utility in the preparation of cereblon‐based degraders (PROTACs, CELMoDs) can be assessed in a single step from inexpensive, commercial α‐bromoglutarimide through a unique Brønsted‐acid assisted Ni‐electrocatalytic approach. The reaction tolerates a broad array of functional groups that are historically problematic and can be applied to the simplified synthesis of dozens of known compounds that have only been procured through laborious, wasteful, multi‐step sequences. The reaction is scalable in both batch and flow and features a trivial procedure wherein the most time‐consuming aspect of reaction setup is weighing out the starting materials.
• 5-Substituted Derivatives of 6-Halogeno-3-((2-(<i>S</i>)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(<i>S</i>)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography
  作者：Yi Zhang、Olga A. Pavlova、Svetlana I. Chefer、Andrew W. Hall、Varughese Kurian、LaVerne L. Brown、Alane S. Kimes、Alexey G. Mukhin、Andrew G. Horti

  DOI：10.1021/jm030432v

  日期：2004.5.1

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.
• Nickel-Catalyzed Asymmetric Decarboxyarylation with NHP Esters of α-Amino Acid to Chiral Benzylamines
  作者：Cheng-Yu Wang、Yu-Ling Huang、Wei-Cheng Xu、Qian Gao、Peng Liu、Yu-Xiang Bi、Guo-Kai Liu、Xi-Sheng Wang

  DOI：10.1021/acs.orglett.3c02431

  日期：2023.9.29

  A nickel-catalyzed asymmetric decarboxyarylation of NHP esters via reductive cross-coupling has been established. Utilizing the NHP of amino acid esters as radical precursors furnishes a new protocol in which structurally diverse chiral benzylamines could be accessible. This method has demonstrated excellent catalytic efficiency, high enantioselective control, mild conditions, and good functional group

  已经建立了镍催化的 NHP 酯通过还原交叉偶联的不对称脱羧基反应。利用氨基酸酯的 NHP 作为自由基前体提供了一种新的方案，其中可以获得结构多样的手性苄胺。该方法具有优异的催化效率、高对映选择性控制、温和的条件和良好的官能团耐受性，从而能够实现生物活性分子和药物的后期修饰。