S-11-(tert-butoxycarbonyl)undecylethanethioate | 858972-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-11-(tert-butoxycarbonyl)undecylethanethioate
• CAS: 858972-38-0
• 化学式: C₁₈H₃₅NO₃S
• 分子量: 345.547
• InChiKey: IEZIAEGOULGKBA-UHFFFAOYSA-N

物化性质

• 沸点：
  447.1±18.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  S-11-(tert-butoxycarbonyl)undecylethanethioate 在 肼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到tert-butyl 11-mercaptoundecylcarbamate
  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：

  氨甲酸,(11-羟基十一烷基)-,1,1-二甲基乙基酯 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 36.0h， 生成 S-11-(tert-butoxycarbonyl)undecylethanethioate
  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

文献信息

• An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates
  作者：Slawomir Lach、Sebastian Demkowicz、Dariusz Witt

  DOI：10.1016/j.tetlet.2013.10.056

  日期：2013.12

  We have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives 1 with functionalized alkyl thiolate anions, generated in situ from thioacetates 2 and sodium methoxide or butylamine. The developed

  我们已经开发了在温和条件下以非常高的收率合成功能化不对称二烷基二硫化物的便捷方法。设计的方法基于（5,5-二甲基-2-硫代氧杂1,3,2-二氧杂磷酰氨基-2-基）-二硫烷基衍生物1与硫代乙酸酯2和钠的原位生成的官能化硫代烷基磺酸盐的反应甲醇或丁胺。所开发的方法允许制备带有其他羟基，羧基，氨基，叠氮基，生物素或马来酰亚胺官能团的不对称二硫键。
• Inkless Microcontact Printing on Self-Assembled Monolayers of Fmoc-Protected Aminothiols
  作者：Alexander A. Shestopalov、Robert L. Clark、Eric J. Toone

  DOI：10.1021/ja076226k

  日期：2007.11.1

  Here we describe a new microcontact printing technique (mu CP), based on a catalytic reaction between an Fmoc-protected self-assembled monolayer (SAM) of aminothiols chemisorbed on a gold surface and an elastomeric stamp bearing covalently attached piperidine. The elastomeric stamp was used to selectively cleave Fmoc groups from the surface of a SAM on gold in the places of conformal contact. The technique permits nanoscale pattern fabrication with edge resolution less than 50 nm, avoiding problems of conventional microcontact printing associated with diffusion of chemical "ink", and provides a simple method for the chemical modification of SAMs.