(2RS,4RS)-4-(叔丁基)-2-(甲硫基)环己酮 | 108920-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2RS,4RS)-4-(叔丁基)-2-(甲硫基)环己酮
• 英文名称: cis-4-tert-Butyl-2-(methylthio)cyclohexanone
• 英文别名: (2R,4R)-4-tert-butyl-2-methylsulfanylcyclohexan-1-one
• CAS: 108920-15-6
• 化学式: C₁₁H₂₀OS
• 分子量: 200.345
• InChiKey: ARPKFFQSQVKRIG-PSASIEDQSA-N

物化性质

• 沸点：
  286.8±33.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2RS,4RS)-4-(叔丁基)-2-(甲硫基)环己酮 生成 (2R,4R)-4-tert-Butyl-1-methylene-2-methylsulfanyl-cyclohexane
  参考文献：
  名称：

  VEDEJS, E.;DENT, W. H., J. AMER. CHEM. SOC., 111,(1989) N7, C. 6861-6862

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基硫代磺酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 trans-4-tert-Butyl-2-(methylthio)cyclohexanone 、 (2RS,4RS)-4-(叔丁基)-2-(甲硫基)环己酮
  参考文献：
  名称：

  Axial/equatorial proportions for 2-substituted cyclohexanones

  摘要：

  Axial-equatorial conformational proportions have been measured for 2-substituted cyclohexanones in chloroform by the Eliel method for F, Cl, Br, I, MeO, MeS, Me2N, MeSe, and Me. For the first seven of these, at least five experimentally independent measurables were used and the resulting conformational preferences appear to be accurate to within 10%. Systematic errors degraded the results for MeSe and Me. For Me2N, the conformational preference also was measured for the first time at slow exchange in the low-temperature C-13 spectrum in several solvents. In chloroform, steric and polar effects contribute to the conformational preferences, with steric effects dominant for large groups such as I and MeS.

  DOI：

  10.1021/jo00079a035

文献信息

• Rhodium-catalyzed α-methylthiolation reaction of unactivated ketones using 1,2-diphenyl-2-methylthio-1-ethanone for the methylthio transfer reagent
  作者：Mieko Arisawa、Fumihiko Toriyama、Masahiko Yamaguchi

  DOI：10.1016/j.tet.2011.01.071

  日期：2011.3

  RhH(PPh3)4, 1,2-bis(diphenylphosphino)ethane (dppe), and dimethyl disulfide, ketones without α-activating groups were α-methylthiolated with 1,2-diphenyl-2-methylthio-1-ethanone giving α-methylthio ketones. The reaction of unsymmetrical ketones proceeded at the more substituted carbons. The initial formation of kinetic α-methylthiolated products followed by their rearrangement to thermodynamic products was

  在催化量的RhH的（PPH的存在3）4，1,2-双（二苯基膦基）乙烷（dppe），和二甲基二硫醚，没有α-活化基团进行了酮α-methylthiolated用1,2-二苯基-2-甲硫基-1-乙酮生成α-甲硫基酮。不对称酮的反应在更多取代的碳上进行。在α-苯基酮的反应中观察到了动力学α-甲基硫醇化产物的最初形成，然后重排为热力学产物。在这些条件下，醛，苯乙酸酯和苯乙腈也被α-甲基硫醇化。
• Rhodium-Catalyzed Methylthio Transfer Reaction between Ketone α-Positions: Reversible Single-Bond Metathesis of C−S and C−H Bonds
  作者：Mieko Arisawa、Katsunori Suwa、Masahiko Yamaguchi

  DOI：10.1021/ol802619e

  日期：2009.2.5

  ophenone giving α-phenylthio-α-methylthio ketones. The methylthio transfer reaction between the ketone α-positions was reversible and at equilibrium, and the methylthio group was transferred in preference to the phenylthio group. The reaction of tertiary alkyl methylthiomethyl ketones proceeded in high yields; the reaction of diastereomeric 4-(tert-butyl)-2-phenylthiocyclohexanones gave an axial 2-methylthiolated

  在催化量的RhH（PPh 3）4和1,2-双（二苯基正膦）乙烷（dppe）存在下，将α-苯硫酮与对氰基-α-甲基硫代苯乙酮进行甲硫醇化，得到α-苯硫基-α-甲硫基酮。酮α-位之间的甲硫基转移反应是可逆的，并且处于平衡状态，甲硫基优先于苯硫基转移。叔烷基甲硫基甲基酮的反应产率高。非对映异构体4-（叔丁基）-2-苯基硫代环己酮的反应得到轴向的2-甲基硫醇化产物。
• Studies on the stereoselectivity of hydride reductions on 2-(methylthio)- and 2-(methylsulfonyl)cyclohexanones
  作者：M. Carmen Carreno、Enrique Dominguez、Jose L. Garcia-Ruano、Almudena Rubio

  DOI：10.1021/jo00392a022

  日期：1987.8
• VEDEJS, E.;DENT, W. H., J. AMER. CHEM. SOC., 111,(1989) N7, C. 6861-6862
  作者：VEDEJS, E.、DENT, W. H.

  DOI：——

  日期：——
• CARRENO, M. CARMEN;DOMINGUEZ, ENRIQUE;GARCIA-RUANO, JOSE L.;RUBIO, ALMUDE+, J. ORG. CHEM., 52,(1987) N 16, 3619-3625
  作者：CARRENO, M. CARMEN、DOMINGUEZ, ENRIQUE、GARCIA-RUANO, JOSE L.、RUBIO, ALMUDE+

  DOI：——

  日期：——