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trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane

中文名称
——
中文别名
——
英文名称
trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane
英文别名
[[[(1R,2R)-2-chlorocyclohexyl]trisulfanyl]-diphenylmethyl]benzene
trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane化学式
CAS
——
化学式
C25H25ClS3
mdl
——
分子量
457.125
InChiKey
TXUWTNFDHOAQOE-DNQXCXABSA-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):
    7.9
  • 重原子数:
    29
  • 可旋转键数:
    7
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.28
  • 拓扑面积:
    75.9
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane乙酸乙酯 为溶剂, 反应 15.0h, 以65%的产率得到(1R,2R)-1-chloro-2-[[(1R,2R)-2-chlorocyclohexyl]tetrasulfanyl]cyclohexane
    参考文献:
    名称:
    Sulfenyl Chloride Chemistry. New Precursors for Diatomic Sulfur Transfer
    摘要:
    When triphenylmethanesulfenyl chloride (1) (or its thio homologue 2) are treated with various bicycles, norbornene (5), or bicyclo[2.2.2]octene (6), dithio adducts 7 and 8 were produced in good isolated yields. Final products were obtained via an episulfide intermediate. The stereochemistry of addition has been determined by X-ray analysis. Treatment of thiosulfenyl chloride 2 (or its dithio homologue 3) with other olefins, cyclopentene (10), cyclohexene (11), or 1,4-dioxene (12), leads to the formation of disulfides (13-15 from 2) and trisulfides (16 and 17 from 3) in high isolated yields (ca. 92%). The structures of 7, 8, and 13-17 were established by H-1 and C-13 NMR and elemental analysis as well as by X-ray determination. When these adducts are warmed with a 1,3-diene 42, they deliver diatomic sulfur-trapped derivatives, cyclic di-49 and tetrasulfide adducts 46. A variety of solvents, temperatures, times, and concentrations were employed to optimize the yield of 46 and 49. The tetrasulfide adduct 46 is quantitatively converted to disulfide 49 with triphenylphosphine; this affords cyclic disulfides in >50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.
    DOI:
    10.1021/jo9710792
  • 作为产物:
    描述:
    triphenylmethanedithiosulfenyl chloride环己烯 以87%的产率得到trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane
    参考文献:
    名称:
    磺酰氯化学。双原子硫转移的前体
    摘要:
    三苯基甲硫基亚硫酰氯1 [(C 6 H 5)3 CSSCl](及其二硫代同系物2 [(C 6 H 5)3 CSSSCl])与环戊烯和环己烯形成稳定的加成产物(产率约85%)。当这些加合物被二烯加热时,它们会释放出双原子的硫捕获的衍生物。用三苯基膦将这些四硫化物定量转化为相应的二硫化物3。这提供了环状二硫化物,从二烯分离出的产率为50%。此外,已经获得了涉及二硫杂环戊烷中间体4的证据。
    DOI:
    10.1016/0040-4039(94)85351-7
  • 作为试剂:
    描述:
    2,3-二甲基-1,3-丁二烯trans-2-chloro-1-(triphenylmethyltrithio)cyclohexane 作用下, 以 乙酸乙酯 为溶剂, 反应 15.0h, 以8%的产率得到1,2-二硫杂-4,5-二甲基-4-环己烯
    参考文献:
    名称:
    Sulfenyl Chloride Chemistry. New Precursors for Diatomic Sulfur Transfer
    摘要:
    When triphenylmethanesulfenyl chloride (1) (or its thio homologue 2) are treated with various bicycles, norbornene (5), or bicyclo[2.2.2]octene (6), dithio adducts 7 and 8 were produced in good isolated yields. Final products were obtained via an episulfide intermediate. The stereochemistry of addition has been determined by X-ray analysis. Treatment of thiosulfenyl chloride 2 (or its dithio homologue 3) with other olefins, cyclopentene (10), cyclohexene (11), or 1,4-dioxene (12), leads to the formation of disulfides (13-15 from 2) and trisulfides (16 and 17 from 3) in high isolated yields (ca. 92%). The structures of 7, 8, and 13-17 were established by H-1 and C-13 NMR and elemental analysis as well as by X-ray determination. When these adducts are warmed with a 1,3-diene 42, they deliver diatomic sulfur-trapped derivatives, cyclic di-49 and tetrasulfide adducts 46. A variety of solvents, temperatures, times, and concentrations were employed to optimize the yield of 46 and 49. The tetrasulfide adduct 46 is quantitatively converted to disulfide 49 with triphenylphosphine; this affords cyclic disulfides in >50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.
    DOI:
    10.1021/jo9710792
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文献信息

  • Sulfenyl chloride chemistry. Precursors for diatomic sulfur transfer
    作者:Imad A. Abu-Yousef、David N. Harpp
    DOI:10.1016/0040-4039(94)85351-7
    日期:1994.9
    [(C6H5)3CSSCl] (and its dithio homolog 2 [(C6H5)3CSSSCl]) give stable addition products (ca. 85% yield) with cyclopentene and cyclohexene. When these adducts are warmed with a diene, they deliver diatomic sulfur-trapped derivatives. These tetrasulfides are quantitatively converted to the corresponding disulfide 3 with triphenylphosphine; this affords cyclic disulfides in & 50% isolated yield from the
    三苯基甲硫基亚硫酰氯1 [(C 6 H 5)3 CSSCl](及其二硫代同系物2 [(C 6 H 5)3 CSSSCl])与环戊烯和环己烯形成稳定的加成产物(产率约85%)。当这些加合物被二烯加热时,它们会释放出双原子的硫捕获的衍生物。用三苯基膦将这些四硫化物定量转化为相应的二硫化物3。这提供了环状二硫化物,从二烯分离出的产率为50%。此外,已经获得了涉及二硫杂环戊烷中间体4的证据。
  • Sulfenyl Chloride Chemistry. New Precursors for Diatomic Sulfur Transfer
    作者:Imad A. Abu-Yousef、David N. Harpp
    DOI:10.1021/jo9710792
    日期:1998.11.1
    When triphenylmethanesulfenyl chloride (1) (or its thio homologue 2) are treated with various bicycles, norbornene (5), or bicyclo[2.2.2]octene (6), dithio adducts 7 and 8 were produced in good isolated yields. Final products were obtained via an episulfide intermediate. The stereochemistry of addition has been determined by X-ray analysis. Treatment of thiosulfenyl chloride 2 (or its dithio homologue 3) with other olefins, cyclopentene (10), cyclohexene (11), or 1,4-dioxene (12), leads to the formation of disulfides (13-15 from 2) and trisulfides (16 and 17 from 3) in high isolated yields (ca. 92%). The structures of 7, 8, and 13-17 were established by H-1 and C-13 NMR and elemental analysis as well as by X-ray determination. When these adducts are warmed with a 1,3-diene 42, they deliver diatomic sulfur-trapped derivatives, cyclic di-49 and tetrasulfide adducts 46. A variety of solvents, temperatures, times, and concentrations were employed to optimize the yield of 46 and 49. The tetrasulfide adduct 46 is quantitatively converted to disulfide 49 with triphenylphosphine; this affords cyclic disulfides in >50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.
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