bicyclo<3.3.1>nonylidenebicyclo<3.3.1>nonanethiirane | 116195-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丙烷
• 英文名称: bicyclo<3.3.1>nonylidenebicyclo<3.3.1>nonanethiirane
• CAS: 116195-02-9
• 化学式: C₁₈H₂₈S
• 分子量: 276.486
• InChiKey: UUEKGDDGLNYCMC-UHFFFAOYSA-N

物化性质

• 沸点：
  407.0±14.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  bicyclo<3.3.1>nonylidenebicyclo<3.3.1>nonanethiirane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以98%的产率得到bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonanethiirane 1-oxide
  参考文献：
  名称：

  Effective Precursors for Sulfur Monoxide Formation

  摘要：

  When triphenylmethanesulfenyl chloride (12) (or its thio 13 or dithio homolog 14) are treated with hindered olefins 15 and 16, thiiranes 10 and 11, are produced in high isolated yields (ca. 94%). Treatment of 10 and 11 with m-chloroperoxybenzoic acid (m-CPBA) leads to the formation of thiirane 1-oxides 8 and 9 (99% isolated yields). The structures of 8-11 were established by H-1 and C-13 NMR, mass spectrometry as well as by X-ray. Thermal decomposition of either 8 or 9 smoothly delivers sulfur monoxide to various 1,3-dienes giving cyclic sulfoxides in good yield. A variety of conditions were employed to optimize the yield of the trapped adducts.

  DOI：

  10.1021/jo9709864
• 作为产物：
  描述：

  bis(bicyclo-<3.3.1>non-9-ylidene) 在 三苯基硫氯甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以93%的产率得到bicyclo<3.3.1>nonylidenebicyclo<3.3.1>nonanethiirane
  参考文献：
  名称：

  Effective Precursors for Sulfur Monoxide Formation

  摘要：

  When triphenylmethanesulfenyl chloride (12) (or its thio 13 or dithio homolog 14) are treated with hindered olefins 15 and 16, thiiranes 10 and 11, are produced in high isolated yields (ca. 94%). Treatment of 10 and 11 with m-chloroperoxybenzoic acid (m-CPBA) leads to the formation of thiirane 1-oxides 8 and 9 (99% isolated yields). The structures of 8-11 were established by H-1 and C-13 NMR, mass spectrometry as well as by X-ray. Thermal decomposition of either 8 or 9 smoothly delivers sulfur monoxide to various 1,3-dienes giving cyclic sulfoxides in good yield. A variety of conditions were employed to optimize the yield of the trapped adducts.

  DOI：

  10.1021/jo9709864

文献信息

• Selective sulfurization of olefins by 9,10-epidithio-9,10-dihydroanthracene: intermediacy of diatomic sulfur
  作者：Wataru Ando、Hideki Sonobe、Takeshi Akasaka

  DOI：10.1016/s0040-4020(01)87816-9

  日期：1990.1

  3-butadienes and electron-rich olefins gave 1,2-dithiins and episulfides, respectively. The reaction is explained in terms of an intermediate anthracene endodisulfide with transfer of singlet diatomic sulfur to the dienes and olefins.

  在1,3-丁二烯存在下，9,10-二氢-9,10-（1,3-二硫代-2-甲基-2-甲基-2-对甲氧基苯基-1-氧化物）丙烷蒽（3）与高氯酸的反应和富含电子的烯烃分别得到1,2-二硫精和环硫化物。用中间体蒽二硫化物来解释该反应，其中单线态双原子硫转移到二烯和烯烃上。
• Generation of Singlet Diatomic Sulfur from 9,10-Epidithio-9,10-dihydroanthracene
  作者：Wataru Ando、Hideki Sonobe、Takeshi Akasaka

  DOI：10.1016/s0040-4039(00)96937-5

  日期：——

  10-dihydroanthracene () was formed as an intermediate in the reaction of 9,10-dihydro-9,10-(1,3-epidithio-2-methano- 2-p-methoxyphenyl-1-oxide)propanoanthracene () with perchloric acid. Singlet diatomic sulfur was generated from endodisulfide and trapped with conjugated dienes.

  新型9,10-epidithio-9,10-dihydroanthracene（）作为中间体在9,10-dihydro-9,10-（1,3-epidithio-2-methano-2-2-p-甲氧基苯基）的反应中形成-1-氧化物）丙烷蒽（）与高氯酸。内二硫化物产生单重态双原子硫，并被共轭二烯捕获。
• 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.
• ANDO, WATARU;SONOBE, HIDEKI;AKASAKA, TAKESHI, TETRAHEDRON LETT., 28,(1987) N 52, 6653-6656
  作者：ANDO, WATARU、SONOBE, HIDEKI、AKASAKA, TAKESHI

  DOI：——

  日期：——