tert-butyl 11-mercaptoundecylcarbamate | 478691-27-9

• 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: tert-butyl 11-mercaptoundecylcarbamate
• 英文别名: tert-butyl N-(11-sulfanylundecyl)carbamate
• CAS: 478691-27-9
• 化学式: C₁₆H₃₃NO₂S
• 分子量: 303.51
• InChiKey: QQNYPGOHICVHIU-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  409.4±18.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 11-mercaptoundecylcarbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以99%的产率得到巯基-十一胺盐酸盐
  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：

  11-aminoundecan-1-ol 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 三苯基膦 、 肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 50.0h， 生成 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

文献信息

• DDQ-mediated synthesis of functionalized unsymmetrical disulfanes
  作者：Mateusz Musiejuk、Tomasz Klucznik、Janusz Rachon、Dariusz Witt

  DOI：10.1039/c5ra04173b

  日期：——

  good yields. The designed method is based on the reaction of bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfane with thiols in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The developed method allows the preparation of unsymmetrical disulfanes bearing additional hydroxy, carboxy, or amino functionalities.

  我们开发了一种简单有效的方法，可在温和条件下以高收率合成功能化的不对称二硫烷。设计的方法基于在2,3-二氯-5,6-存在下双（5,5-二甲基-2-硫代氧杂1,3,2-二氧杂磷酰氨基-2-基）二硫醚与硫醇的反应。双氰基苯醌（DDQ）。所开发的方法允许制备带有额外的羟基，羧基或氨基官能团的不对称二硫烷。
• Efficient Synthesis of Functionalized Unsymmetrical Dialkyl Trisulfanes
  作者：Dariusz Witt、Slawomir Lach

  DOI：10.1055/s-0033-1338966

  日期：——

  We have developed a convenient method for the synthesis of functionalized unsymmetrical dialkyl trisulfanes 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 with alkyl disulfanyl anions generated in situ from S-acetyl disulfanyl derivatives and sodium methoxide. The developed method

  我们开发了一种方便的方法，可以在温和的条件下以非常好的收率合成功能化的不对称二烷基三硫烷。所设计的方法基于 (5,5-二甲基-2-硫代-1,3,2-二氧杂膦基-2-基)-二硫烷基衍生物与 S-乙酰二硫烷基衍生物和钠原位生成的烷基二硫烷基阴离子的反应。甲醇。所开发的方法允许制备在三硫烷官能团两侧带有额外羟基、羧基或氨基官能团的不对称三硫烷。
• 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。
• Novel and Efficient Synthesis of Unsymmetrical Trisulfides
  作者：Dariusz Witt、Slawomir Lach、Magdalena Sliwka-Kaszynska

  DOI：10.1055/s-0030-1259033

  日期：2010.12

  We have developed a convenient method for the synthesis of unsymmetricaltrisulfides under mild conditions in very good yields. The designedmethod is based on the straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecanefrom readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane,sulfur dichloride (SCl 2 ) and dodecane-1-thiol. The

  我们开发了一种在温和条件下以非常好的产率合成不对称三硫化物的简便方法。设计的方法基于从容易获得的 5,5-二甲基-2-硫烷基中直接制备 1-[(5,5-二甲基-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane- 2-thioxo-1,3,2-dioxaphosphorinane、二氯化硫 (SCl 2 ) 和十二烷-1-硫醇。不对称三硫化物也可以从脂肪族、芳香族硫醇和 L-半胱氨酸衍生物中获得。
• A Novel and Efficient Synthesis of Unsymmetrical Disulfides
  作者：Dariusz Witt、Sylwia Antoniow

  DOI：10.1055/s-2007-965873

  日期：2007.2

  method for the synthesis of unsymmetrical trisulfides under mild conditions in very good yields. The designed method is based on the straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane, sulfur dichloride (SCl 2 ) and dodecane-1-thiol. The unsymmetrical trisulfides can

  我们开发了一种在温和条件下以非常好的收率合成不对称三硫化物的简便方法。所设计的方法基于从容易获得的 5,5-二甲基-2-直接制备 1-[(5,5-二甲基-2-硫代-1,3,2-二氧磷环-2-基)三硫基]十二烷。 sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane、二氯化硫 (SCl 2 ) 和十二烷-1-硫醇。不对称三硫化物也可以从脂肪族、芳香族硫醇和 L-半胱氨酸衍生物中获得。