(6S,9R)-6-(1-methylethyl)-9-methyl-1,4-dithiaspiro[4,5]decane | 140386-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6S,9R)-6-(1-methylethyl)-9-methyl-1,4-dithiaspiro[4,5]decane
• 英文别名: (6S,9R)-6-isopropyl-9-methyl-1,4-dithiaspiro[4.5]decane；(1R,4S)-3,3-ethylenedothiomenthane；l-menthone dithiolane；(6s,9r)-6-(1-Methylethyl)-9methyl-1,4-dithiaspiro[4,5]decane；(6S,9R)-9-methyl-6-propan-2-yl-1,4-dithiaspiro[4.5]decane
• CAS: 140386-41-0
• 化学式: C₁₂H₂₂S₂
• 分子量: 230.439
• InChiKey: DNXUKZZSEGMLQQ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6S,9R)-6-(1-methylethyl)-9-methyl-1,4-dithiaspiro[4,5]decane 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 4.0h， 以70%的产率得到(4R,5S,6S,9R)-6-isopropyl-9-methyl-1,4-dithiaspiro[4,5]decane-1,1,4-trioxide
  参考文献：
  名称：

  Asymmetrical oxidation of menthone dithiolane

  摘要：

  Asymmetrical oxidation was performed of menthone dithiolane obtained in 95-98% yield by condensation of menthone with 1,2-ethanedithiol in the presence of boron trifluoride etherate. 6-Isopropyl-9-methyl-1,4-dithiaspiro[4,5] decane-1,4-dioxide (yield 5-55%) and 6-isopropyl-9-methyl-1,4-dithiaspiro[ 4,5]-decane-1,1,4-trioxide (yield 65-70%) were synthesized. Chemical structures of compounds obtained were proved by XRD analysis, NMR and IR spectroscopy.

  DOI：

  10.1134/s1070428008070166
• 作为产物：
  描述：

  (1R,4R,6R)-1-isopropyl-4-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one 在 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 29.0h， 生成 (6S,9R)-6-(1-methylethyl)-9-methyl-1,4-dithiaspiro[4,5]decane
  参考文献：
  名称：

  Thiylation of (R)-4-Menthen-3-one and Its Derivatives

  摘要：

  研究了(R)-4-薄荷烯-3-酮及其衍生物的硫化反应。合成了新的薄荷烷系列硫化物和亚砜。

  DOI：

  10.1007/s10600-013-0766-y

文献信息

• Solvent Free Thioacetalization of Carbonyl Compounds Catalyzed by Cu(OTf)₂-SiO₂
  作者：R. Vijaya Anand、P. Saravanan、Vinod K. Singh

  DOI：10.1055/s-1999-2635

  日期：1999.4

  Aldehydes and ketones were thioacetalyzed using 1,2-ethanedithiol in the presence of a catalytic amount of Cu(OTf)2-SiO2 under solvent free conditions in excellent yields.

  醛和酮在无溶剂条件下，使用1,2-乙二硫醇，在催化量的Cu(OTf)2-SiO2存在下，进行了硫代乙酰化反应，产率极佳。
• Synthesis of several optically active menthane disulfides and thiosulfinates
  作者：E. S. Izmest′ev、D. V. Sudarikov、S. A. Rubtsova、A. V. Kuchin

  DOI：10.1007/s10600-011-9827-2

  日期：2011.3

  Symmetric and asymmetric disulfides were synthesized from mixtures of menthyl- and neomenthylthiols and were oxidized asymmetrically. Dineomenthyldisulfide, dimenthyldisulfide, and menthylneomenthyldisulfide were synthesized in yields of 47–48%, 24–25, and 29–55, respectively. Pure diastereomeric dimenthyl-, dineomenthyl-, and menthylneomenthylthiosulfinates were synthesized in yields of 85–90% and de up to 30%.

  用薄荷硫醇和新薄荷硫醇的混合物合成了对称和不对称二硫化物，并进行了不对称氧化。合成的二乙烯基二硫化物、二甲基二硫化物和薄荷基新甲基二硫化物的产率分别为 47-48%、24-25%和 29-55%。纯非对映的二甲基、二乙烯基和薄荷基新甲基硫代磺酸盐的合成率分别为 85-90%和 30%。
• H-y zeolite, an efficient catalyst for thioacetalization
  作者：Pradeep Kumar、Ravinder S. Reddy、Anand P. Singh、Bipin Pandey

  DOI：10.1016/s0040-4039(00)77725-2

  日期：1992.2

  Carbonyl compounds are thioacetalized by 1,2-ethanedithiol in presence of H-Y zeolite in almost quantitative yields (> 90%).
• Syntheses of Chiral Menthyl and Neomenthyl Sulfides, sulfoxides and sulfones
  作者：Jos� Manuel Blanco、Olga Caama�o、Franco Fern�ndez、Isabel Nieto

  DOI：10.1002/prac.199533701115

  日期：——

  Attempts to synthesize stereospecifically menthanethiol (2) and menthyl thiocyanate (3) from suitable electrophilic neomenthyl substrates (4a-c), and a variety of sulfur nucleophiles failed or predominantly led to beta-elimination products. Almost quantitative yields of mixtures of 2 and its 3-epimer (8) were obtained by reductive cleavage of (-)-3-menthone ethylene dithioacetal (7), but stereoselectivity was low (ratio of 2/8, 41:59) and the mixture could not be resolved. Recrystallization and subsequent oxidation of the dinitrophenyl sulfides of 2 and 8 allowed the isolation of the dinitrophenyl menthyl and neomenthyl sulfoxides (12 and 13, respectively), and an irresolvable mixture of the sulfones 14 and 15.