3-exo-(heptafluoroisopropyl)-2-endo-iodobicyclo[2.2.1]heptane | 34542-08-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-exo-(heptafluoroisopropyl)-2-endo-iodobicyclo[2.2.1]heptane
• 英文别名: 2-iodo-3-(perfluoroisopropyl)norbornane
• CAS: 34542-08-0
• 化学式: C₁₀H₁₀F₇I
• 分子量: 390.083
• InChiKey: YRJNAMQZJQVOQJ-BWBBJGPYSA-N

物化性质

• 沸点：
  229.8±35.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 七氟-2-碘代丙烷 在 sodium 4-methylbenzenesulfinate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以58%的产率得到3-exo-(heptafluoroisopropyl)-2-endo-iodobicyclo[2.2.1]heptane
  参考文献：
  名称：

  Reaction of perfluoroalkyl iodides with electron-donor nucleophiles. Addition of perfluoroalkyl iodides to olefins initiated by electron transfer

  摘要：

  DOI：

  10.1021/jo00218a006

文献信息

• Perfluoroalkylation of thiols. Evidence for a radical chain process
  作者：Andrew E. Feiring

  DOI：10.1016/s0022-1139(00)85203-3

  日期：1984.2

  Perfluoroalkyl sulfides are formed from primary or secondary perfluoroalkyl iodides and aromatic or aliphatic thiolates without UV irradiation. Perfluoroalkyl radicals are intermediates as demonstrated by inhibition and trapping studies.

  全氟烷基硫化物是由伯或仲全氟烷基碘化物和芳香族或脂肪族硫醇盐形成的，无需紫外线照射。全氟烷基是抑制和捕获研究证明的中间体。
• Sodium dithionite initiated regio- and stereoselective radical addition of polyfluoroalkyl iodide with norbornene analogs
  作者：Fanhong Wu、Fanhua Xiao、Xianjin Yang、Yongjia Shen、Tieying Pan

  DOI：10.1016/j.tet.2006.08.042

  日期：2006.10

  Sodium dithionite initiated free-radical addition of polyfluoroalkyl iodides (2m-2s) with norbornene la and its derivatives, such as norbomene-2-carboxylates 1b and 1c, and norbornene-2-carboxylic acids 1d and le was investigated. In all the cases, the addition of R-F group was stereoselectively delivered at exo-position and the predominant configuration of products was trans. Under the similar condition, norbomene-2-carboxylic ethyl ester 1b reacted with 2p to give 6-exo-R-F-5-endo-iodo adduct 3bp and 5-exo-R-F-6-endo-iodo adduct 5bp in the ratio of 4:1. While 1c, which has a heavy crowded group in the 2-endo-position, gave 6-exo-RF-5-endo-iodo adduct 3cp and polyfluoro-alkylated product 4cp retaining the trans-configuration and the exo-orientation of R-F group. The fluoroalkylation-lactonization reaction occurred in the reaction of norbomene-2-endo-carboxylic acids Id and le with polyfluoroalkyl iodides to afford the corresponding fluoro-alkylated gamma-lactone products (7dp-7ds, and 7em-7er). The configuration of the products was further confirmed by 2D NMR and X-ray diffraction analyses for the first time. (c) 2006 Elsevier Ltd. All rights reserved.