ethyl 2,2-difluoro-4-iodooctanoate | 127224-09-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2,2-difluoro-4-iodooctanoate
• 英文别名: 2,2-Difluoro-4-iodooctanoic acid ethyl ester
• CAS: 127224-09-3
• 化学式: C₁₀H₁₇F₂IO₂
• 分子量: 334.145
• InChiKey: ZPLWAFGFAOZMRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluoro-4-iodooctanoate 在 水 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到ethyl 2,2-difluorooctanoate
  参考文献：
  名称：

  A new approach to .alpha.,.alpha.-difluoro-functionalized esters

  摘要：

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.

  DOI：

  10.1021/jo00017a026
• 作为产物：
  描述：

  正癸烯 、 二氟碘乙酸乙酯 在 四氢吡咯 、 联苯乙醛 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以40%的产率得到ethyl 2,2-difluoro-4-iodooctanoate
  参考文献：
  名称：

  烯胺和胺协同催化的未活化烯烃的可见光诱导自由基碘过氟烷基化

  摘要：

  进行了无金属可见光诱导的全氟烷基碘的ATRA。该反应对各种全氟烷基碘和未活化的烯烃和炔烃有效，并且在1 mol％的醛和胺的条件下可以顺利进行。

  DOI：

  10.1002/ejoc.201901896

文献信息

• Intermolecular Iodofluoroalkylation of Unactivated Alkynes and Alkenes Mediated by Manganese Catalysts
  作者：Yun‐Xing Ji、Lu‐Jun Wang、Wei‐Si Guo、Qirui Bi、Bo Zhang

  DOI：10.1002/adsc.201901556

  日期：2020.3.4

  An approach for iodofluoroalkylation of unactivated alkynes and alkenes facilitated by an earth‐abundant and inexpensive manganese catalyst, Mn2(CO)10, is reported. This protocol employs visible light as the energy input and shows a wide substrate scope and high functional‐group compatibility. A variety of synthetically useful fluoroalkylated alkyl and alkenyl iodides can be prepared in moderate to

  报道了一种通过富含地球的廉价锰催化剂Mn 2（CO）10促进未活化炔烃和烯烃的碘氟烷基化的方法。该协议采用可见光作为能量输入，并显示了广泛的基板范围和高度的功能组兼容性。可以以中等至优异的产率制备各种合成上有用的氟代烷基化的烷基和链烯基碘。该反应具有高效，操作简便，可扩展性以及出色的化学，区域和E / Z选择性的特点。
• Atom transfer radical additions (ATRAs) promoted by catalytic amounts of amines: The effective iododifluoroalkylation of alkenes/alkynes
  作者：Qi-Ping Huang、Jia Jia、Wei-Piao Li、An-Jun Wang、Liang Zhao

  DOI：10.1080/00397911.2021.1918173

  日期：——

  an attractive method access to fluoro-containing compounds, and most of those reactions were promoted by visible light and stoichiometric electron-donor compounds. Here, a novel atom transfer radical addition (ATRA) reaction promoted by catalytic amount of 1,4-dimethylpiperazine at heating condition is developed. This protocol enables a simple and practical alternative for the effective iododifluoroalkylation

  摘要 最近，通过非共价相互作用（卤素键或 EDA 复合物）引发的氟烷基化反应已成为一种有吸引力的方法，可获取含氟化合物，其中大部分反应是由可见光和化学计量电子给体化合物促进的。在这里，开发了一种在加热条件下由催化量的 1,4-二甲基哌嗪促进的新型原子转移自由基加成 (ATRA) 反应。该协议为烯烃或炔烃的有效碘二氟烷基化提供了一种简单实用的替代方案，其特点是合成简单、底物范围广和产品转化的可行性。
• Copper catalyzed addition reaction of iododifluoroacetates to olefins
  作者：Zhen-Yu Yang、Donald J. Burton

  DOI：10.1016/s0022-1139(00)82877-8

  日期：1989.12

  The addition of iododifluoroacetates to alkenes is catalyzed by copper powder (10-20 mol %) at 50° to 60°C. The reaction can be carried out neat or in hexane or benzene as solvent. Both terminal and internal alkenes gave good yields (65-83%). Reduction of the adduct with tributyltin hydride provides the α, α-difluoroacetate.

  在50℃至60℃下，通过铜粉（10-20mol％）将碘代二氟乙酸酯加到烯烃中。该反应可以在纯溶剂中或在己烷或苯作为溶剂中进行。末端烯烃和内部烯烃均具有良好的收率（65-83％）。用氢化三丁基锡还原加合物得到α，α-二氟乙酸酯。
• Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate
  作者：Fanhua Xiao、Fanhong Wu、Yongjia Shen、Lifang Zhou

  DOI：10.1016/j.jfluchem.2004.10.009

  日期：2005.1

  A novel synthesis of alpha,alpha-difluoro-gamma-butyrolactones was realized by the alkaline hydrolysis of the adducts of ethyl iododifluoroacetate and alkenes. Ethyl iododifluoroacetate reacted with alkenes in the presence of sodium dithionite to give the addition products in 62-78% yields. The products were hydrolyzed in 10% aqueous sodium carbonate solution to give alpha,alpha-difluoro-gamma-butyrolactones in 93-98% yields. (C) 2004 Elsevier B.V. All rights reserved.
• YANG, ZHEN-YU;BURTON, DONALD J., J. FLUOR. CHEM., 45,(1989) N, C. 435-439
  作者：YANG, ZHEN-YU、BURTON, DONALD J.

  DOI：——

  日期：——