10-Ethoxycarbonylmethylsulfanyl-12,12-difluoro-dodec-11-enoic acid methyl ester | 334529-35-0

• 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: 10-Ethoxycarbonylmethylsulfanyl-12,12-difluoro-dodec-11-enoic acid methyl ester
• 英文别名: methyl 10-(2-ethoxy-2-oxoethyl)sulfanyl-12,12-difluorododec-11-enoate
• CAS: 334529-35-0
• 化学式: C₁₇H₂₈F₂O₄S
• 分子量: 366.47
• InChiKey: QGCHJWUTQJRXJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  巯基乙酸乙酯 、 10-Ethoxycarbonylmethylsulfanyl-12,12-difluoro-dodec-11-enoic acid methyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到(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：

  巯基乙酸乙酯 、 methyl (E)-12-bromo-12,12-difluorododec-10-enoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以52%的产率得到10-Ethoxycarbonylmethylsulfanyl-12,12-difluoro-dodec-11-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