(E)-1,2-difluoro-1-iodo-2-phenylethene | 201793-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1,2-difluoro-1-iodo-2-phenylethene
• 英文别名: (E)-1,2-difluoro-1-iodo-2-phenylethylene；[(E)-1,2-difluoro-2-iodoethenyl]benzene
• CAS: 201793-69-3
• 化学式: C₈H₅F₂I
• 分子量: 266.029
• InChiKey: ARSTWHUSZIDOJZ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-十二炔 、 (E)-1,2-difluoro-1-iodo-2-phenylethene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以73%的产率得到(Z)-1,2-difluoro-1-phenyltetradec-1-en-3-yne
  参考文献：
  名称：

  通过新型的碱催化环化反应从（E）-单氟炔类化合物中进行3-氟-1-取代萘的位点特异性制备。

  摘要：

  报道了用于制备3-氟-1-取代的萘的新型环化反应。由（Z）-1-溴-1-氟烯烃通过Sonogashira偶联反应制得的（E）-单氟炔烃经过环化反应，以DABCO或DBU处理时，以良好或优异的收率得到3-氟-1-取代的萘。在回流的N-甲基-2-吡咯烷酮（NMP）中。[反应：看文字]

  DOI：

  10.1021/ol060785z
• 作为产物：
  描述：

  (Z)-α,β-difluorostyrene 在 正丁基锂 、 碘 作用下， 生成 (E)-1,2-difluoro-1-iodo-2-phenylethene
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-α,β-Difluorostyrenes and Stereospecific Conversion to (E)-α,β-Difluoro-β-iodostyrenes¹

  摘要：

  Substituted aromatic iodides coupled with (E)-HFC=CFZnI: (E:Z 95:5) under mild conditions, in the presence of catalytic Pd(PPh3)(4) in DMF to give (Z)-alpha,beta-difluorostyrenes in good yields. The coupling reaction was tolerant of a variety of functionalities. Isomerically pure (Z)-alpha,beta-difluorostyrenes were readily converted to the corresponding (E)-alpha,beta-difluoro-beta-iodostyrenes in good yields by two methods; in one method, treatment of the (Z)-alpha,beta-difluorostyrenes with LTMP at low-temperature gave vinyllithium reagents which were captured in situ with Bu3SnCl to form vinylstannanes. The intermediate vinylstannanes could be isolated or treated directly with I-2 to give (E)-alpha,beta-difluoro-beta-iodostyrenes in a one-flask procedure. In a second approach, n-BuLi was utilized to pregenerate vinyllithium reagents which were quenched with I-2 to afford (E)-alpha,beta-difluoro-beta-iodostyrenes.

  DOI：

  10.1021/jo971434o

文献信息

• CROSSLINKING AGENT AND FLUORINE-CONTAINING AROMATIC COMPOUND
  申请人：Nichias Corporation

  公开号：EP3187527B1

  公开（公告）日：2019-10-30
• Site-Specific Preparation of 3-Fluoro-1-substituted-naphthalenes via a Novel Base-Catalyzed Cyclization Reaction from (<i>E</i>)-Monofluoroenynes
  作者：Jianjun Xu、Yi Wang、Donald J. Burton

  DOI：10.1021/ol060785z

  日期：2006.6.1

  A novel cyclization reaction for the preparation of 3-fluoro-1-substituted-naphthalenes is reported. (E)-Monofluoroenynes, which are prepared by Sonogashira coupling reaction from (Z)-1-bromo-1-fluoroalkenes, undergo cyclization to afford 3-fluoro-1-substituted-naphthalenes in good to excellent yields when treated with DABCO or DBU in refluxing N-methyl-2-pyrrolidinone (NMP). [reaction: see text]

  报道了用于制备3-氟-1-取代的萘的新型环化反应。由（Z）-1-溴-1-氟烯烃通过Sonogashira偶联反应制得的（E）-单氟炔烃经过环化反应，以DABCO或DBU处理时，以良好或优异的收率得到3-氟-1-取代的萘。在回流的N-甲基-2-吡咯烷酮（NMP）中。[反应：看文字]
• Stereoselective Preparation of (<i>Z</i>)-α,β-Difluorostyrenes and Stereospecific Conversion to (<i>E</i>)-α,β-Difluoro-β-iodostyrenes¹
  作者：Charles R. Davis、Donald J. Burton

  DOI：10.1021/jo971434o

  日期：1997.12.1

  Substituted aromatic iodides coupled with (E)-HFC=CFZnI: (E:Z 95:5) under mild conditions, in the presence of catalytic Pd(PPh3)(4) in DMF to give (Z)-alpha,beta-difluorostyrenes in good yields. The coupling reaction was tolerant of a variety of functionalities. Isomerically pure (Z)-alpha,beta-difluorostyrenes were readily converted to the corresponding (E)-alpha,beta-difluoro-beta-iodostyrenes in good yields by two methods; in one method, treatment of the (Z)-alpha,beta-difluorostyrenes with LTMP at low-temperature gave vinyllithium reagents which were captured in situ with Bu3SnCl to form vinylstannanes. The intermediate vinylstannanes could be isolated or treated directly with I-2 to give (E)-alpha,beta-difluoro-beta-iodostyrenes in a one-flask procedure. In a second approach, n-BuLi was utilized to pregenerate vinyllithium reagents which were quenched with I-2 to afford (E)-alpha,beta-difluoro-beta-iodostyrenes.