(S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone | 851010-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone
• 英文别名: [(2S)-2-[hydroxy(diphenyl)methyl]pyrrolidin-1-yl]-(4-pyrrolidin-1-ylpyridin-3-yl)methanone
• CAS: 851010-73-6
• 化学式: C₂₇H₂₉N₃O₂
• 分子量: 427.546
• InChiKey: UCOBCJJFWYAFNU-VWLOTQADSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  652.0±55.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone 、 碘甲烷 以 二氯甲烷 为溶剂， 生成 3-[(S)-2-(Hydroxy-diphenyl-methyl)-pyrrolidine-1-carbonyl]-1-methyl-4-pyrrolidin-1-yl-pyridinium; iodide
  参考文献：
  名称：

  Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives

  摘要：

  开发了一类新型 4-N,N-二烷基氨基吡啶手性酰基转移催化剂，该催化剂能够利用范德华（π）和氢键相互作用，通过远程手性信息立体化学控制仲醇的动力学解析，并具有中等至卓越的选择性（s = 6-30）。由 (S)-α,α-二芳基脯氨醇衍生的催化剂大大优于没有叔羟基的类似物，并且在广泛的底物中具有高活性和高选择性。

  DOI：

  10.1039/b604632k
• 作为产物：
  描述：

  4-氯烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 30.0h， 生成 (S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone
  参考文献：
  名称：

  Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues

  摘要：

  我们报道了一种新型易制备的手性4-(吡咯烷基)-吡啶催化剂的开发，该催化剂能够利用范德华（π）和氢键相互作用，从而允许远程手性信息通过立体化学控制仲醇的动态拆分。

  DOI：

  10.1039/b419335k
• 作为试剂：
  描述：

  2-甲基-1-苯基-1-丙醇 、 乙酸酐 在 (S)-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)(4-(pyrrolidin-1-yl)pyridin-3-yl)methanone 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以26%的产率得到
  参考文献：
  名称：

  (S)-Proline-Derived Catalysts for the Acylative Kinetic Resolution of Alcohols: A Remote Structural Change Allows a Complete Selectivity Switch

  摘要：

  A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (S)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolution of secondary alcohols with the opposite sense of enantiodiscrimination to that observed when the substituent is capable of accepting hydrogen bonds.

  DOI：

  10.1055/s-0033-1339286

文献信息

• Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
  作者：Ciarán Ó Dálaigh、Stephen J. Hynes、Declan J. Maher、Stephen J. Connon

  DOI：10.1039/b419335k

  日期：——

  We report the development of a new class of readily prepared chiral 4-(pyrrolidino)-pyridine catalysts capable of exploiting both van der Waals (π) and H-bonding interactions, thus allowing remote chiral information to stereochemically control the kinetic resolution of sec-alcohols.

  我们报道了一种新型易制备的手性4-(吡咯烷基)-吡啶催化剂的开发，该催化剂能够利用范德华（π）和氢键相互作用，从而允许远程手性信息通过立体化学控制仲醇的动态拆分。
• (S)-Proline-Derived Catalysts for the Acylative Kinetic Resolution of Alcohols: A Remote Structural Change Allows a Complete Selectivity Switch
  作者：Stephen Connon、Oliver Gleeson、Yurii Gun'ko

  DOI：10.1055/s-0033-1339286

  日期：——

  A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (S)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolution of secondary alcohols with the opposite sense of enantiodiscrimination to that observed when the substituent is capable of accepting hydrogen bonds.
• Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives
  作者：Ciarán Ó. Dálaigh、Stephen J. Hynes、John E. O'Brien、Thomas McCabe、Declan J. Maher、Graeme W. Watson、Stephen J. Connon

  DOI：10.1039/b604632k

  日期：——

  The development of a new class of chiral 4-N,N-dialkylaminopyridine acyl-transfer catalysts capable of exploiting both van der Waals (π) and H-bonding interactions to allow remote chiral information to stereochemically control the kinetic resolution of sec-alcohols with moderate to excellent selectivity (s = 6–30). Catalysts derived from (S)-α,α-diarylprolinol are considerably superior to analogues devoid of a tertiary hydroxyl moiety and possess high activity and selectivity across a broad range of substrates.

  开发了一类新型 4-N,N-二烷基氨基吡啶手性酰基转移催化剂，该催化剂能够利用范德华（π）和氢键相互作用，通过远程手性信息立体化学控制仲醇的动力学解析，并具有中等至卓越的选择性（s = 6-30）。由 (S)-α,α-二芳基脯氨醇衍生的催化剂大大优于没有叔羟基的类似物，并且在广泛的底物中具有高活性和高选择性。