methyl (E)-12-bromo-12,12-difluorododec-10-enoate | 154389-27-2

• 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 (E)-12-bromo-12,12-difluorododec-10-enoate
• 英文别名: methyl-12-bromo-12,12-difluorododec-10-enoate
• CAS: 154389-27-2
• 化学式: C₁₃H₂₁BrF₂O₂
• 分子量: 327.209
• InChiKey: NDHIXGAKRQPOSV-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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 (E)-12-bromo-12,12-difluorododec-10-enoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-12-Ethoxycarbonylmethylsulfanyl-12,12-difluoro-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：

  10-烯酸甲酯 在 aluminum oxide 、 chromium chloride 、 potassium fluoride 、 铁粉 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 methyl (E)-12-bromo-12,12-difluorododec-10-enoate
  参考文献：
  名称：

  A convenient synthesis of bromodifluoromethyl-substituted alkenes

  摘要：

  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.

  DOI：

  10.1016/0022-1139(93)03051-m

文献信息

• Organic Dye-Catalyzed Atom Transfer Radical Addition–Elimination (ATRE) Reaction for the Synthesis of Perfluoroalkylated Alkenes
  作者：Deo Prakash Tiwari、Saumya Dabral、Jian Wen、Jan Wiesenthal、Steven Terhorst、Carsten Bolm

  DOI：10.1021/acs.orglett.7b01952

  日期：2017.8.18

  An atom transfer radical addition elimination (ATRE) reaction of terminal alkenes with perfluoroalkyl halides under visible light is described. The photoredox catalysis with Eosin Y provides perfluoroalkenes in good yields. The reaction has been utilized for the late stage perfluoroalkenylation of an estrone-derived alkene.

  描述了在可见光下末端烯烃与全氟烷基卤化物的原子转移自由基加成消除（ATRE）反应。曙红Y的光氧化还原催化以良好的产率提供了全氟烯烃。该反应已用于雌酮衍生的烯烃的全氟烯基的晚期反应。
• 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.
• 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.
• Iododifluoromethyl alkenes [ICF2CHCHR]: a labile system generated from 1,1-difluoro-1,3-diiodoalkanes and its trapping with nucleophiles
  作者：Yong Guo、Qing-Yun Chen

  DOI：10.1016/s0022-1139(00)00341-9

  日期：2001.1

  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.