tert-butyl (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)-2-ethynylpyrrolidine-1-carboxylate | 833473-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)-2-ethynylpyrrolidine-1-carboxylate
• 英文别名: (2S,4R)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-ethynylpyrrolidine-1-carboxylate；tert-Butyl (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)-2-ethynylpyrrolidine-1-carboxylate；tert-butyl (2S,4R)-4-[tert-butyl(diphenyl)silyl]oxy-2-ethynylpyrrolidine-1-carboxylate
• CAS: 833473-56-6
• 化学式: C₂₇H₃₅NO₃Si
• 分子量: 449.665
• InChiKey: ABRLUNULLFPOFJ-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)-2-ethynylpyrrolidine-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(2S,4R)-tert-butyl 2-ethynyl-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors

  摘要：

  A novel class of pyrrolidinyl-acetyleneic thieno[3,2-d]pyrimidines has been identified which potently inhibit the EGFR and ErbB-2 receptor tyrosine kinases. Synthetic modifications of the pyrrolidine carbamate moiety result in a range of effects on enzyme and cellular potency. In addition, the impact of the absolute stereochemical configuration on cellular potency and oral mouse pharmacokinetics is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.023
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 咪唑 、 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 tert-butyl (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)-2-ethynylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  脯氨酸衍生的氨基三唑配体：在钌催化的不对称转移加氢中的制备和使用

  摘要：

  2-三唑基和由2- triazolylmethylpyrrolidines的制备大号脯氨酸和大号-反式-4-羟基脯氨酸进行了说明，以它们作为钌催化不对称转移氢化手性配体的评价沿。还介绍了通过引入远程取代基进行配体的模块化演化，显示出对配体性能的出乎意料的重要影响。

  DOI：

  10.1002/adsc.201000678

文献信息

• [EN] KRAS G12C INHIBITORS<br/>[FR] INHIBITEURS DE KRAS G12C
  申请人：[en]FRONTIER MEDICINES CORPORATION

  公开号：WO2023081840A1

  公开（公告）日：2023-05-11

  The present disclosure provides compounds and methods useful in the treatment and suppression of cancer, for example, useful for treating or suppressing cancers characterized by KRAS G12C. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
• Synthesis and stereochemical effects of pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines as EGFR and ErbB-2 inhibitors
  作者：Kirk L. Stevens、Krystal J. Alligood、Jennifer G. Badiang Alberti、Thomas R. Caferro、Stanley D. Chamberlain、Scott H. Dickerson、Hamilton D. Dickson、Holly K. Emerson、Robert J. Griffin、Robert D. Hubbard、Barry R. Keith、Robert J. Mullin、Kimberly G. Petrov、Roseanne M. Gerding、Michael J. Reno、Tara R. Rheault、David W. Rusnak、Douglas M. Sammond、Stephon C. Smith、David E. Uehling、Alex G. Waterson、Edgar R. Wood

  DOI：10.1016/j.bmcl.2008.11.023

  日期：2009.1

  A novel class of pyrrolidinyl-acetyleneic thieno[3,2-d]pyrimidines has been identified which potently inhibit the EGFR and ErbB-2 receptor tyrosine kinases. Synthetic modifications of the pyrrolidine carbamate moiety result in a range of effects on enzyme and cellular potency. In addition, the impact of the absolute stereochemical configuration on cellular potency and oral mouse pharmacokinetics is described. (C) 2008 Elsevier Ltd. All rights reserved.
• Proline-Derived Aminotriazole Ligands: Preparation and Use in the Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation
  作者：Xacobe C. Cambeiro、Miquel A. Pericàs

  DOI：10.1002/adsc.201000678

  日期：2011.1.10

  The preparation of 2‐triazolyl‐ and 2‐triazolylmethylpyrrolidines from L‐proline and L‐trans‐4‐hydroxyproline is described, along with their evaluation as chiral ligands in ruthenium‐catalyzed asymmetric transfer hydrogenation. Modular evolution of the ligands by introduction of remote substituents is also presented, showing a surprisingly important effect on the performance of the ligands.

  2-三唑基和由2- triazolylmethylpyrrolidines的制备大号脯氨酸和大号-反式-4-羟基脯氨酸进行了说明，以它们作为钌催化不对称转移氢化手性配体的评价沿。还介绍了通过引入远程取代基进行配体的模块化演化，显示出对配体性能的出乎意料的重要影响。