5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid bis(2-diphenylphosphanyl-ethyl)amide | 66561-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid bis(2-diphenylphosphanyl-ethyl)amide
• 英文别名: N,N-Bis<2-(diphenylphosphino)ethyl>biotinamide；5-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid bis-(2-diphenylphosphanyl-ethyl)-amide；N,N-Bis(2-diphenylphosphinoethyl)biotinamid；biotin bis-(2-diphenylphosphanyl-ethyl)-amide；1H-Thieno[3, N,N-bis[2-(diphenylphosphino)ethyl]hexahydro-2-oxo-；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N,N-bis(2-diphenylphosphanylethyl)pentanamide
• CAS: 66561-97-5
• 化学式: C₃₈H₄₃N₃O₂P₂S
• 分子量: 667.792
• InChiKey: YQGVXWZSNIQEOR-IWQNTTPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯基膦 在 盐酸 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid bis(2-diphenylphosphanyl-ethyl)amide
  参考文献：
  名称：

  Synthesis of functional chelating diphosphines containing the bis[2-(diphenylphosphino)ethyl]amino moiety and the use of these materials in the preparation of water-soluble diphosphine complexes of transition metals

  摘要：

  DOI：

  10.1021/jo00327a005
• 作为试剂：
  描述：

  2-乙酰氨基丙烯酸 在 acetate buffer 、 S₁₁₂G streptavidin mutant bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoic acid bis(2-diphenylphosphanyl-ethyl)amide 作用下， 以 二甲基亚砜 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 24.0h， 生成 N-乙酰-D-丙氨酸
  参考文献：
  名称：

  Artificial Metalloenzymes:  (Strept)avidin as Host for Enantioselective Hydrogenation by Achiral Biotinylated Rhodium−Diphosphine Complexes

  摘要：

  We report on the generation of artificial metalloenzymes based on the noncovalent incorporation of biotinylated rhodium-diphosphine complexes in (strept)avidin as host proteins. A chemogenetic optimization procedure allows one to optimize the enantioselectivity for the reduction of acetamidoacrylic acid (up to 96% ee (R) in streptavidin S112G and up to 80% ee (S) in WT avidin). The association constant between a prototypical cationic biotinylated rhodium-diphosphine catalyst precursor and the host proteins was determined at neutral pH: log K-a = 7.7 for avidin (pl = 10.4) and log K-a = 7.1 for streptavidin (pl = 6.4). It is shown that the optimal operating conditions for the enantioselective reduction are 5 bar at 30 degreesC with a 1% catalyst loading.

  DOI：

  10.1021/ja0476718

文献信息

• Bis(2-diphenylphosphinoethyl)amine. A flexible synthesis of functionalized chelating diphosphines
  作者：Michael E. Wilson、Ralph G. Nuzzo、George M. Whitesides

  DOI：10.1021/ja00475a069

  日期：1978.3
• Synthesis of functional chelating diphosphines containing the bis[2-(diphenylphosphino)ethyl]amino moiety and the use of these materials in the preparation of water-soluble diphosphine complexes of transition metals
  作者：Ralph G. Nuzzo、Sharon L. Haynie、Michael E. Wilson、George M. Whitesides

  DOI：10.1021/jo00327a005

  日期：1981.7