trans 18 Ethyl 2,2-Difluoro-2-(2-iodocyclohexyl)acetate | 134682-32-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: trans 18 Ethyl 2,2-Difluoro-2-(2-iodocyclohexyl)acetate
• 英文别名: trans-ethyl-α,α-difluoro-(2-iodocyclohexanyl)acetate；ethyl 2,2-difluoro-2-(2-iodocyclohexyl)acetate；trans-ethyl 2,2-difluoro-2-(2-iodocyclohexyl)acetate
• CAS: 134682-32-9
• 化学式: C₁₀H₁₅F₂IO₂
• 分子量: 332.129
• InChiKey: IRHNYNMTZJJHNF-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans 18 Ethyl 2,2-Difluoro-2-(2-iodocyclohexyl)acetate 在 sodium carbonate 作用下， 反应 4.0h， 以98%的产率得到3,3-difluorohexahydrocyclohexyl[b]furan-2-one
  参考文献：
  名称：

  Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2004.10.009
• 作为产物：
  描述：

  二氟碘乙酸乙酯 、 环己烯 在 偶氮二异丁腈 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 trans 18 Ethyl 2,2-Difluoro-2-(2-iodocyclohexyl)acetate 、 Ethyl 2,2-Difluoro-2-(2-iodocyclohexyl)acetate
  参考文献：
  名称：

  方便的AIBN引发的碘代二氟乙酸乙酯向烯烃的自由基加成反应

  摘要：

  描述了由AIBN引发的4-碘-2，2-二氟乙酸乙酯向各种烯烃底物中的加成。该加成通常导致相应的加成产物以良好的至优异的产率，并且在反应条件下可以容许各种官能团。

  DOI：

  10.1016/j.jfluchem.2008.03.002

文献信息

• A convenient AIBN-initiated radical addition of ethyl iododifluoroacetate to alkenes
  作者：Leo Leung、Bruno Linclau

  DOI：10.1016/j.jfluchem.2008.03.002

  日期：2008.10

  The AIBN-initiated addition of ethyl 4-iodo-2,2-difluoroacetate to a variety of alkene substrates is described. The addition generally led to the corresponding addition products in good to excellent yields and various functional groups could be tolerated under the reaction conditions.

  描述了由AIBN引发的4-碘-2，2-二氟乙酸乙酯向各种烯烃底物中的加成。该加成通常导致相应的加成产物以良好的至优异的产率，并且在反应条件下可以容许各种官能团。
• A new approach to .alpha.,.alpha.-difluoro-functionalized esters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00017a026

  日期：1991.8

  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.
• 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。
• 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.