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trans-1-Fluoro-2-(methylthio)cyclododecane | 122895-31-2

中文名称
——
中文别名
——
英文名称
trans-1-Fluoro-2-(methylthio)cyclododecane
英文别名
(1R,2R)-1-fluoro-2-methylsulfanylcyclododecane
trans-1-Fluoro-2-(methylthio)cyclododecane化学式
CAS
122895-31-2
化学式
C13H25FS
mdl
——
分子量
232.406
InChiKey
HLTWZCNLCKRJKC-CHWSQXEVSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.8
  • 重原子数:
    15
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    25.3
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

  • 作为产物:
    描述:
    环十二碳烯 、 dimethyl(methylthio)sulfonium tetrafluoroborate 在 triethylamine tris-hydrofluoride 作用下, 生成 trans-1-Fluoro-2-(methylthio)cyclododecane
    参考文献:
    名称:
    Formal addition of methanesulfenyl fluoride to unsaturated substrates
    摘要:
    DOI:
    10.1016/s0040-4039(00)86045-1
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文献信息

  • Formal addition of methanesulfenyl fluoride to unsaturated substrates
    作者:Günter Haufe、Gérard Alvernhe、Daniel Anker、André Laurent、Christine Saluzzo
    DOI:10.1016/s0040-4039(00)86045-1
    日期:1988.1
  • HAUFE, GUNTER;ALVERNHE, GERARD;ANKER, DANIEL;LAURENT, ANDRE;SALUZZO, CHRI+, TETRAHEDRON LETT., 29,(1988) N 19, 2311-2314
    作者:HAUFE, GUNTER、ALVERNHE, GERARD、ANKER, DANIEL、LAURENT, ANDRE、SALUZZO, CHRI+
    DOI:——
    日期:——
  • Synthesis of fluoroalkyl methyl thioethers by formal addition of methanesulfenyl fluoride to alkenes
    作者:Gunter Haufe、Gerard Alvernhe、Daniel Anker、Andre Laurent、Christine Saluzzo
    DOI:10.1021/jo00028a056
    日期:1992.1
    The electrophilic anti-1,2-addition of the elements of methanesulfenyl fluoride to carbon-carbon double bonds by a one-pot reaction of dimethyl(methylthio)sulfonium tetrafluoroborate and triethylamine trishydrofluoride with various types of alkenes is used for the synthesis of beta-fluoroalkyl methyl thioethers. This reaction is stereospecific: starting from cis-cycloalkenes (1) trans-1-fluoro-2-(methylthio)cycloalkanes (2) are formed, while trans-cyclododecene (3) gives the cis product 4 everytime in good yields. With unsymmetrical alkenes these reactions proceed regioselectively to produce Markovnikov-oriented fluoro thioethers. With 2,6-norbornadiene (26) exclusive exo attack on one double bond and subsequent transannular participation of the second pi-bond gives rise to two isomeric 3,5-disubstituted nortricyclanes, 28 and 29, while starting from the medium-sized cis,cis-1,5-cyclooctadiene (10) no transannular pi-participation is observed: the trans-1,2-addition product to one of the two double bonds in 11 is isolated. In contrast, in the reaction of the monoepoxide 30 of this diene in addition to the simple 1,2-adduct 31 a transannular oxygen participation occurs producing three oxa bicyclic compounds 32-34. The oxidation of 1-fluoro-2-(methylthio)cyclooctane (2a) by sodium periodate yields the expected mixture of two diastereomeric 1-fluoro-2-(methylsulfinyl)cyclooctanes (36) which on pyrolysis give 3-fluorocyclooctene (37).
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