O-(11-phenylmethoxyundec-1-en-6-yl) methylsulfanylmethanethioate | 1043905-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(11-phenylmethoxyundec-1-en-6-yl) methylsulfanylmethanethioate
• CAS: 1043905-78-7
• 化学式: C₂₀H₃₀O₂S₂
• 分子量: 366.589
• InChiKey: YYAGRBJAADTKAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-(11-phenylmethoxyundec-1-en-6-yl) methylsulfanylmethanethioate 在 偶氮二异丁腈 、 2-苯基-1,2,4-三唑-3-亚基硼烷 作用下， 以 苯 为溶剂， 反应 2.0h， 以67%的产率得到(((5-(2-methylcyclopentyl)pentyl)oxy)methyl)benzene
  参考文献：
  名称：

  Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor

  摘要：

  Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 Kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 Kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.

  DOI：

  10.1021/ja804150k
• 作为产物：
  描述：

  、 碘甲烷 以 四氢呋喃 为溶剂， 以440 mg的产率得到O-(11-phenylmethoxyundec-1-en-6-yl) methylsulfanylmethanethioate
  参考文献：
  名称：

  Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor

  摘要：

  Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 Kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 Kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.

  DOI：

  10.1021/ja804150k

文献信息

• Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes
  作者：Shau-Hua Ueng、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

  DOI：10.1021/ol101015m

  日期：2010.7.2

  Minimalist N-heterocyclic carbene boranes 1,3-dimethylimidazol-2-ylideneborane and 2,4-dimethyl-1,2,4-triazol-3-ylideneborane are readily available and have low molecular weights. They exhibit superior performance to first-generation NHC−boranes, providing improved yields in reductions of xanthates and related functional groups.

  极简主义的N-杂环卡宾硼烷1,3-二甲基咪唑-2-亚基硼烷和2,4-二甲基-1,2,4-三唑-3-亚基硼烷很容易获得，并且分子量低。它们表现出优于第一代NHC-硼烷的性能，在减少黄药和相关官能团方面提供了更高的收率。