2-氟-3,4-二碘吡啶 | 153034-83-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氟-3,4-二碘吡啶
• 英文名称: 2-fluoro-3,4-diiodopyridine
• CAS: 153034-83-4
• 化学式: C₅H₂FI₂N
• 分子量: 348.885
• InChiKey: JPNTYYOJYPWUSU-UHFFFAOYSA-N

物化性质

• 沸点：
  307℃
• 密度：
  2.662
• 闪点：
  140℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为产物：
  描述：

  2-氟吡啶 在 正丁基锂 、 二异丙胺 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 2-氟-3,4-二碘吡啶
  参考文献：
  名称：

  四碳链吡啶酮的光环加成。分子内氢键和近端仲醇促进酰胺水解。

  摘要：

  四碳束缚的吡啶酮经历光环加成反应，只得到反式[4 + 4]产物。系链醇的存在通过与相邻的吡啶酮的分子内氢键键合而使环加成反应的溶剂依赖性非对映选择性。环加成后，该醇可将羰基传递至近端受阻酰胺氮，导致酰胺水解非常容易。

  DOI：

  10.1021/jo025565n

文献信息

• Heteroaryl fused azapolycyclic compounds
  申请人：Allen P. Martin

  公开号：US20050020830A1

  公开（公告）日：2005-01-27

  The present invention provides a compound having the structure of formula I: wherein R 1 is hydrogen, (C 1 -C 6 ) alkyl, unconjugated (C 3 -C 6 ) alkenyl, benzyl, YC(═O)(C 1 -C 6 ) alkyl or —CH 2 CH 2 —O—(C 1 -C 4 ) alkyl; X is CH 2 or CH 2 CH 2 ; Y is (C 2 -C 6 ) alkylene; Z is (CH 2 ) m , CF 2 , or C(═O), where m is 0, 1 or 2; R 2 and R 3 are selected independently from hydrogen, halogen, —(C 1 -C 6 ) alkyl optionally substituted with from 1 to 7 halogen atoms, and —O(C 1 -C 6 ) alkyl optionally substituted with from 1 to 7 halogen atoms, or R 2 and R 3 each together with the atom to which it is connected independently form C(═O), S→O, S(═O) 2 , or N→O; and is a 5- to 7-membered monocyclic heteroaryl group selected from pyridinyl, pyridone, pyridazinyl, imidazolyl, pyrimidinyl, pyrazolyl, triazolyl, pyrazinyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl, isothiazolyl, pyrrolyl, cinnolinyl, triazinyl, oxadiazolyl, thiadiazolyl and furazanyl groups.

  本发明提供了一种具有以下结构的化合物：其中R1为氢、(C1-C6)烷基、非共轭(C3-C6)烯基、苄基、YC(═O)(C1-C6)烷基或—CH2CH2—O—(C1-C4)烷基；X为CH2或CH2CH2；Y为(C2-C6)亚烯基；Z为(CH2)m、CF2或C(═O)，其中m为0、1或2；R2和R3分别选择自氢、卤素、—(C1-C6)烷基（可选地取代1至7个卤素原子）、和—O(C1-C6)烷基（可选地取代1至7个卤素原子），或者R2和R3每个与其连接的原子独立地形成C(═O)、S→O、S(═O)2或N→O；和为从吡啶基、吡啶酮基、吡啶嗪基、咪唑基、嘧啶基、吡唑基、三唑基、吡嗪基、呋喃基、噻吩基、异噁唑基、噁唑基、异硫咪唑基、吡咯基、喹啉基、三嗪基、噁二唑基、噻二唑基和呋喃基组成的5-至7-环单环杂芳基。
• Novel preparation of functionalized iodotetrahydronaphthyridine, iodoazaindoline, and iodotetrahydropyridoazepine systems
  作者：Hanh Nho Nguyen、Zhan J. Wang

  DOI：10.1016/j.tetlet.2007.08.076

  日期：2007.10

  A novel method, which utilizes a key halogen dance step for the preparation of iodotetrahydronaphthyridine, iodoazaindoline, and iodotetrahydropyridoazepine ring-systems is described. A variety of transformations of the iodo-functional group are also reported to demonstrate the utility of this method. Published by Elsevier Ltd.
• First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis
  作者：P. Rocca、C. Cochennec、F. Marsais、L. Thomas-dit-Dumont、M. Mallet、A. Godard、G. Queguiner

  DOI：10.1021/jo00079a031

  日期：1993.12

  Metalation of iodopyridines was successfully achieved by LDA at low temperature. In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro-and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key molecules for the synthesis of fused polyaromatic alkaloids. Thus, perlolidine, delta-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling.
• Photocycloaddition of Four-Carbon-Tethered Pyridones. Intramolecular Hydrogen Bonding and Facilitated Amide Hydrolysis by a Proximal Secondary Alcohol¹
  作者：Man Zhu、Zhilei Qiu、Gary P. Hiel、Scott McN. Sieburth

  DOI：10.1021/jo025565n

  日期：2002.5.1

  of a tether alcohol engenders a solvent-dependent diastereoselectivity for the cycloaddition by intramolecular hydrogen bonding to the adjacent pyridone. Following cycloaddition, the alcohol can deliver a carbonyl group to the proximal, hindered amide nitrogen, leading to a very facile amide hydrolysis.

  四碳束缚的吡啶酮经历光环加成反应，只得到反式[4 + 4]产物。系链醇的存在通过与相邻的吡啶酮的分子内氢键键合而使环加成反应的溶剂依赖性非对映选择性。环加成后，该醇可将羰基传递至近端受阻酰胺氮，导致酰胺水解非常容易。