methyl 10,12-dibromo-12,12-difluorododecanoate | 125081-47-2

• 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: methyl 10,12-dibromo-12,12-difluorododecanoate
• CAS: 125081-47-2
• 化学式: C₁₃H₂₂Br₂F₂O₂
• 分子量: 408.121
• InChiKey: RPGNKSXTZMSLGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  methyl 10,12-dibromo-12,12-difluorododecanoate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-12,12-Difluoro-12-phenylsulfanyl-dodec-10-enoic acid methyl ester
  参考文献：
  名称：

  Iododifluoromethyl alkenes [ICF2CHCHR]: a labile system generated from 1,1-difluoro-1,3-diiodoalkanes and its trapping with nucleophiles

  摘要：

  Treatment of 1,1-difluoro- 1,3-diiodoalkanes (ICF2CH2CHIR1. 1) with NEt3 in various solvents or with KF/Al2O3/CH3CN gave no alkenes (ICF2CH=CHR1, 2), whereas with NaOH afforded alpha,beta -unsaturated carboxylic acids, although a signal of 2 in F-19 NMR spectroscopy could be observed momentarily sometimes. However, the labile 2 can be trapped either with thiolate or phenoxide ions. The former reaction gives a mixture of CF2=CHCH(SR)R-1 and RSCF2CH=CHR1, whereas the latter affords only ArOCF2CH=CHR1. The nucleophilic substitution of the bromoanalogues, BrCF2CH,CHBrR1 and BrCF2CH=CHR1, has also been investigated. A mechanism involving S(N)2' and an allene intermediate is proposed. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00341-9
• 作为产物：
  描述：

  二溴二氟甲烷 、 10-烯酸甲酯 在 三乙基硼 作用下， 以 正己烷 为溶剂， 反应 10.0h， 以90%的产率得到methyl 10,12-dibromo-12,12-difluorododecanoate
  参考文献：
  名称：

  三乙基硼烷诱导的全氟烷基碘向乙炔的立体选择性自由基加成

  摘要：

  在催化量的三乙基硼烷的存在下，用全氟烷基碘处理带有各种取代基的末端或内部乙炔，可以以良好或极好的收率得到相应的全氟烯烃。还描述了将全氟烷基碘化物加到烯烃中。

  DOI：

  10.1016/s0040-4039(00)99190-1

文献信息

• A convenient synthesis of bromodifluoromethyl-substituted alkenes
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)03051-m

  日期：1994.10

  Various functionalized bromodifluoromethyl-substituted alkenes have been prepared by addition of dibromodifluoromethane to functionalized alkenes promoted by a CrCl3/Fe bimetal redox system, followed by dehydrobromination with KF/Al2O3.
• Synthesis of bromodifluoromethyl-substituted alkenes. Potassium fluoride supported on alumina as a dehydrobrominating agent
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)02954-d

  日期：1994.1

  Potassium fluoride supported on alumina is an efficient dehydrobrominating agent. 1,3-Dibromo-1,1-difluoroalkanes - adducts of dibromodifluoromethane and alkenes - give bromodifluoromethyl-substituted alkenes 2 on dehydrobromination with this agent in good to excellent yields. Alkenes 2 were a mixture of Z- and E-isomers, with the former predominating. Functional groups such as ester, carbonyl, ethylenic and chloromethyl are not affected under such reaction conditions.
• TAKEYAMA, YOSHIHIRO;ICHINOSE, YOSHIFUMI;OSHIMA, KOICHIRO;UTIMOTO, KIITIRO, TETRAHEDRON LETT., 30,(1989) N4, C. 3159-3162
  作者：TAKEYAMA, YOSHIHIRO、ICHINOSE, YOSHIFUMI、OSHIMA, KOICHIRO、UTIMOTO, KIITIRO

  DOI：——

  日期：——