(S)-ethyl 2-(((S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)amino)-4-methylpentanoate | 1141929-15-8

• 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)-ethyl 2-(((S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)amino)-4-methylpentanoate
• 英文别名: (S)-ethyl 2-{[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]amino}-4-methylpentanoate；N-[(S)-1-(4-Bromophenyl)-2,2,2-trifluoroethyl]-L-leucine ethyl ester；ethyl (2S)-2-[[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]amino]-4-methylpentanoate
• CAS: 1141929-15-8
• 化学式: C₁₆H₂₁BrF₃NO₂
• 分子量: 396.247
• InChiKey: ADTBBEUUZHJCOH-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-亮氨酸乙酯 、 (1R)-1-(4-bromophenyl)-2,2,2-trifluoroethyl trifluoromethanesulfonate 在 potassium carbonate 作用下， 以 环己烷 为溶剂， 反应 12.0h， 以94%的产率得到(S)-ethyl 2-(((S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)amino)-4-methylpentanoate
  参考文献：
  名称：

  非外消旋α-三氟甲基苄基三氟甲磺酸的亲核取代

  摘要：

  提出了通过对映体富集的α-三氟甲基苄基三氟甲磺酸酯的亲核置换引入手性α-三氟甲基苄基部分的有效方案。通过测量置换产物的非对映异构体或对映体过量，研究了底物电子学，溶剂极性，温度和碱的影响，这些置换产物是通过将各种α-三氟甲基苄基三氟甲磺酸酯与一系列亲核试剂（包括胺，羧酸盐，硫醇和丙二酸酯。还报道了初步研究以阐明亲核取代反应中苄基中心立体化学完整性的丧失所涉及的机制。

  DOI：

  10.1016/j.tet.2008.12.064

文献信息

• A Practical Enantioselective Synthesis of Odanacatib, a Potent Cathepsin K Inhibitor, via Triflate Displacement of an α-Trifluoromethylbenzyl Triflate
  作者：Paul D. O’Shea、Cheng-yi Chen、Danny Gauvreau、Francis Gosselin、Greg Hughes、Christian Nadeau、Ralph P. Volante

  DOI：10.1021/jo8020314

  日期：2009.2.20

  An enantioselective synthesis of the Cathepsin K inhibitor odanacatib (MK-0822) 1 is described. The key step involves the novel stereospecific S(N)2 triflate displacement of a chiral alpha-trifluoromethylbenzyl triflate 9a with (S)-gamma-fluoroleucine ethyl ester 3 to generate the required alpha-trifluoromethylbenzyl amino stereocenter. ne triflate displacement is achieved in high yield (95%) and minimal loss of stereochemistry. The overall synthesis of I is completed in 6 steps in 61% overall yield.
• [EN] PHOTOCHEMICAL PROCESS FOR THE FLUORINATION OF AN ORGANIC COMPOUND HAVING AN UNACTIVATED SP3 C-H BOND<br/>[FR] PROCÉDÉ PHOTOCHIMIQUE DE FLUORATION D'UN COMPOSÉ ORGANIQUE PRÉSENTANT UNE LIAISON C-H SP3 NON ACTIVÉE
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2015000076A9

  公开（公告）日：2015-08-06
• [EN] PHOTOCHEMICAL PROCESS FOR THE FLUORTNATION OF AN ORGANIC COMPOUND HAVING AN UNACTIVATED SP3 C-H BOND<br/>[FR] PROCÉDÉ PHOTOCHIMIQUE DE FLUORATION D'UN COMPOSÉ ORGANIQUE PRÉSENTANT UNE LIAISON C-H SP3 NON ACTIVÉE
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2015000076A1

  公开（公告）日：2015-01-08

  The application provides a photochemical process for the chemoselective fluorination of an organic compound by combining a carbon-containing compound having an unactivated sp3 C-H bond with a reagent system comprised of a fluorinating agent, and a photocatalyst, in the presence of a light source. Provided as fluorinating agent is N-fluorobenzenesulfonimide (NFSI) or 1-chloromethy1-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™), as photocatalyst is tetrabutylammonium decatungstate (TBADT), and as light source is a 365 nm UV lamp. The reactions conditions result in the C-H bond being replaced by a C-F bond, to provide a fluorinated carbon-containing compound.