thioacetic acid S-6-(adamant-1'-yl)hexyl ester | 858972-37-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: thioacetic acid S-6-(adamant-1'-yl)hexyl ester
• 英文别名: S-[6-(1-adamantyl)hexyl] ethanethioate
• CAS: 858972-37-9
• 化学式: C₁₈H₃₀OS
• 分子量: 294.502
• InChiKey: CBGZEILTPYFRTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±11.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  thioacetic acid S-6-(adamant-1'-yl)hexyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以86%的产率得到6-(adamant-1'-yl)hexanethiol
  参考文献：
  名称：

  Immobilization of Rhodium Complexes at Thiolate Monolayers on Gold Surfaces:  Catalytic and Structural Studies

  摘要：

  Chiral rhodium-diphosphine complexes have been incorporated into self-assembled thiolate monolayers (SAMS) on gold colloids. Catalysts of this type are of interest because they combine properties of homogeneous and heterogeneous systems. In addition, it should be possible to influence the catalytic properties of the metal center by the neighboring thiolate molecules. Colloids with a diameter of ca. 3 nm, coated with a mixed monolayer of n-octanethiolates and thiolates with chiral rhodium-PYRPHOS end groups, were studied as hydrogenation catalysts. With methyl a-acetamido-cinnamate as substrate, virtually the same enantioselectivities (up to 93% ee) and full conversion were obtained as with the corresponding homogeneous [Rh(COD)(PYRPHOS)]BArF catalyst. The colloids were easily recovered by filtration and reused as catalysts three times without loss of enantioselectivity. STM studies of analogous SAMS on Au(111) gave a detailed picture of the structure and dynamics of mixed monolayers of this type. The STM images showed that the catalyst-bearing thiolates are distributed statistically on the surface and that the ordered structure of the n-octanethiolate SAM can be retained during incorporation of the catalyst-bearing thiols using the place-exchange methodology.

  DOI：

  10.1021/ja0500714
• 作为产物：
  描述：

  1-(2-溴乙基)金刚烷 在 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 thioacetic acid S-6-(adamant-1'-yl)hexyl ester
  参考文献：
  名称：

  Immobilization of Rhodium Complexes at Thiolate Monolayers on Gold Surfaces:  Catalytic and Structural Studies

  摘要：

  Chiral rhodium-diphosphine complexes have been incorporated into self-assembled thiolate monolayers (SAMS) on gold colloids. Catalysts of this type are of interest because they combine properties of homogeneous and heterogeneous systems. In addition, it should be possible to influence the catalytic properties of the metal center by the neighboring thiolate molecules. Colloids with a diameter of ca. 3 nm, coated with a mixed monolayer of n-octanethiolates and thiolates with chiral rhodium-PYRPHOS end groups, were studied as hydrogenation catalysts. With methyl a-acetamido-cinnamate as substrate, virtually the same enantioselectivities (up to 93% ee) and full conversion were obtained as with the corresponding homogeneous [Rh(COD)(PYRPHOS)]BArF catalyst. The colloids were easily recovered by filtration and reused as catalysts three times without loss of enantioselectivity. STM studies of analogous SAMS on Au(111) gave a detailed picture of the structure and dynamics of mixed monolayers of this type. The STM images showed that the catalyst-bearing thiolates are distributed statistically on the surface and that the ordered structure of the n-octanethiolate SAM can be retained during incorporation of the catalyst-bearing thiols using the place-exchange methodology.

  DOI：

  10.1021/ja0500714