adamantylideneadamantanethiirane | 62281-75-8

• 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: adamantylideneadamantanethiirane
• 英文别名: 2,2'-epithio-2-(2'-adamantyl)adamantane
• CAS: 62281-75-8
• 化学式: C₂₀H₂₈S
• 分子量: 300.508
• InChiKey: IULDRVGQUIRUGM-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  9.0
• 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：

  adamantylideneadamantanethiirane 在 碘甲烷 作用下， 反应 16.0h， 以100%的产率得到2-(2-adamantylidene)adamantane
  参考文献：
  名称：

  Reaction of sulfur halides with unsaturated compounds

  摘要：

  DOI：

  10.1007/bf00955982
• 作为产物：
  描述：

  2-(2-adamantylidene)adamantane 在 xenon fluoride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 adamantylideneadamantanethiirane
  参考文献：
  名称：

  尝试通过硫属元素镧和噻吨鎓盐的脱烷基化反应合成硫杂环丁烷，硒杂环戊烷和硫杂环丁烷。

  摘要：

  Thiiranium盐[AD 2 SR] + X - （5，8，9，11，12 ; X - = TF 2 Ñ -铁蛋白（Tf = CF 3 SO 2），的SbCl 6 - ）和seleniranium盐[AD 2 SER] + X - （14，16，17，23 - 25 ; X - = TF 2 ñ -，BF 4 -，CHB 11氯11 - ，的SbCl 6 - ）从应变烯烃二（金刚烷基）（合成1）。二硫化物和diselenides（ME 3 SICH 2 CH 2 E）2（4，13），（吨BuMe 2 SICH 2 CH 2 E）2（7，22），和（NCCH 2 CH 2 E）2（10，15 ; E = S，Se）已被使用。ii盐[吨卜2 c ^ 2 SR] + X - （34）和[AD 2 c ^ 2 SR] + X - （35，36）从所制备的双-叔-butylacetylene（2）和双-金刚烷基乙炔（3）

  DOI：

  10.1002/chem.202003461

文献信息

• A novel method for thiiranation of alkenes with 1,1′-dithiobis(1H-1,2,4-triazole)
  作者：Yoshiaki Sugihara、Kaoru Onda、Miho Sato、Takahito Suzuki

  DOI：10.1016/j.tetlet.2010.05.138

  日期：2010.8

  1′-dithiobis(1H-1,2,4-triazole) 4 at −15 °C to form the corresponding thiiranes in moderate to good yields. The thiiranations of anti- and syn-9,9′-bibenzonorbornenylidenes and cis- and trans-cyclooctenes with 4 proceeded with retention of configuration of the starting alkenes.

  八个烯烃在-15°C下与1,1'-二硫代双（1 H -1,2,4-三唑）4反应，以中等至良好的产率形成相应的噻喃。的thiiranations抗和-顺式- bibenzonorbornenylidenes -9,9'-和顺-和反式与-cyclooctenes 4进行与起始烯烃的结构的保持。
• Synthesis of Isolable Thiirane 1-Imides and Their Stereospecific Ring-enlargement to 1,2-Thiazetidines
  作者：Yoshiaki Sugihara、Yui Aoyama、Haruki Okada、Juzo Nakayama

  DOI：10.1246/cl.2008.658

  日期：2008.6.5

  The isolation of thiirane 1-imides was achieved via imination of anti- and syn-9,9′-bibenzonorbornenylidene sulfides by Chloramine T at room temperature, followed by crystallization of the reaction mixture at −18 °C. Allowing CD2Cl2 solutions of the thiirane 1-imides stand at room temperature or heating their crystals to around 120 °C led to the formation of the corresponding 1,2-thiazetidines with retention of the configuration of the thiirane 1-imides.

  通过在室温下用氯胺T进行反式和顺式9,9'-双苯并诺布尔烯腈硫化物的重氮化反应，成功隔离了噻吡喃1-亚胺，随后在-18°C下对反应混合物进行结晶。让噻吡喃1-亚胺的CD2Cl2溶液在室温下静置或将它们的晶体加热至约120°C，会导致相应的1,2-噻唑烷形成，同时保留噻吡喃1-亚胺的立体构型。
• A useful precursor for sulfur monoxide transfer
  作者：Imad A. Abu-Yousef、David N. Harpp

  DOI：10.1016/0040-4039(94)02247-9

  日期：1995.1

  adamantylideneadamantane (11), adamantylideneadamantane thiirane (12) is produced (92%). Compound 12 was treated with m-chloroperoxybenzoic acid (m-CPBA) forming adamantylideneadamantane thiirane 1-oxide (13) in 99% isolated yield. The structures of 12 and 13 were established by 1H and 13C NMR, mass spectrometry as well as by X-ray analysis. Sulfoxide 13 decomposes smoothly to deliver sulfur monoxide in good yield

  当将三苯基甲亚磺酰氯（8）（或其硫代9和二硫代10的同系物）用金刚烷金刚烷（11）处理时，产生金刚烷金刚烷硫杂烷（12）。用间氯过氧苯甲酸（m-CPBA）处理化合物12，以99％的分离产率形成金刚烷内金刚烷噻吩基1-氧化物（13）。通过1 H和13 C NMR，质谱以及X射线分析确定12和13的结构。亚砜13顺利分解，以高收率将一氧化硫输送到各种二烯。
• Reaction of singlet oxygen with thiirane: Implication for a spirodioxathiirane intermediate
  作者：Wataru Ando、Hideki Sonobe、Takeshi Akasaka

  DOI：10.1016/s0040-4039(00)84982-5

  日期：1986.1

  oxygenation of biadamantylidene thiirane afforded, in addition to the corresponding thiirane oxide, the desulfurization products i.e., biadamantylidene and its oxidized products, dioxetane and oxirane, via a spirodioxathiirane intermediate.

  除了相应的硫杂氧杂环丁烷氧化物之外，双金刚烷硫杂环丁烷的光敏氧化还提供了经由螺二氧杂环丁烷中间体的脱硫产物，即金刚烷及其氧化产物，二氧杂环丁烷和环氧乙烷。
• 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.