3-[(4-methylphenyl)sulfinyl]-1,1,1-trifluoro-2-(N-carbobenzoxy)-hex-5-enyl-2-amine | 219953-64-7

• 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: 3-[(4-methylphenyl)sulfinyl]-1,1,1-trifluoro-2-(N-carbobenzoxy)-hex-5-enyl-2-amine
• CAS: 219953-64-7
• 化学式: C₂₁H₂₂F₃NO₃S
• 分子量: 425.472
• InChiKey: KAUGNWSFHFLTNB-HPQBIULASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[(4-methylphenyl)sulfinyl]-1,1,1-trifluoro-2-(N-carbobenzoxy)-hex-5-enyl-2-amine 在 2,4,6-三甲基吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[(2S,3S)-3-chloro-1,1,1-trifluorohex-5-en-2-yl]-N-(4-methylphenyl)sulfanylcarbamate
  参考文献：
  名称：

  “非氧化”氯-Pummerer 反应：新型立体特异性进入邻氯胺和氮丙啶

  摘要：

  本文介绍了一种新的、有用的合成工具，即“非氧化性”氯-Pummerer 反应 (NOCPR)，它允许使用对映异构纯的 α-Li 烷基亚砜作为手性 α-氯代烷基碳负离子与 N 保护的亚胺。在该反应中，衍生自芳基-、氟烷基-和烷基亚胺的 N-烷氧基羰基-β-亚磺酰基胺的亚磺酰基在一锅反应中被氯原子取代，并在碳上进行了彻底的立体转化。通过 NOCPR 产生的几种 1,2-氯胺转化为相应的氮丙啶。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200210)2002:19<3336::aid-ejoc3336>3.0.co;2-t
• 作为产物：
  描述：

  (R)-1-(but-3-ene-1-sulfinyl)-4-methyl-benzene 在 ammonium cerium(IV) nitrate 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 3-[(4-methylphenyl)sulfinyl]-1,1,1-trifluoro-2-(N-carbobenzoxy)-hex-5-enyl-2-amine
  参考文献：
  名称：

  Stereocontrolled approaches to (+)- and (−)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere

  摘要：

  Two efficient approaches to both enantiomers of syn-gamma-triffuoromethyl gamma-amino beta-hydroxy butyric acid (gamma-Tfm-GABOB) (10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed 'non-oxidative' Pummerer reaction, by means of which ex-lithium alkyl sulfoxides are used as chiral alpha-hydroxyalkyl anion equivalents in the synthesis of beta-amino alcohols. Trifluoropyruvaldehyde-N,S-ketal (R)-11, a novel stereochemically stable synthetic equivalent of alpha-amino trifluoropropanal, is used in the second approach. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00397-8

文献信息

• Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containing peptides as inhibitors of HIV-1 protease and MMP-9
  作者：Cristina Pesenti、Alberto Arnone、Stefano Bellosta、Pierfrancesco Bravo、Monica Canavesi、Eleonora Corradi、Massimo Frigerio、Stefano V Meille、Mara Monetti、Walter Panzeri、Fiorenza Viani、Romina Venturini、Matteo Zanda

  DOI：10.1016/s0040-4020(01)00543-9

  日期：2001.7

  We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor pepstatin incorporating two γ-Tfm-γ-amino-β-hydroxybutyric acid (γ-Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-substituted precursors were tested as inhibitors of HIV-1 protease and Gelatinase B (MMP-9)

  我们描述了天冬氨酸蛋白酶抑制剂胃抑素的三氟甲基（Tfm）类似物的不对称总合成，该蛋白结合了两个γ-Tfm-γ-氨基-β-羟基丁酸（γ-Tfm-GABOB）单元而不是天然他汀类单元。测试了标题化合物以及几种Tfm取代的前体作为HIV-1蛋白酶和明胶酶B（MMP-9）的抑制剂
• The ‘non-oxidative’ chloro-Pummerer reaction: a highly stereoselective entry to β-chloro amines and aziridines
  作者：Alessandro Volonterio、Pierfrancesco Bravo、Cristina Pesenti、Matteo Zanda

  DOI：10.1016/s0040-4039(01)00651-7

  日期：2001.6

  Enantiomerically pure a-Li alkyl-sulfoxides can be used as chiral cl-chloroalkyl carbanions with N-protected imines by means of the 'non-oxidative' chloro-Pummerer reaction (NOCPR). This novel methodology allows for a one-pot displacement of a sulfinyl group by chlorine from N-alkoxycarbonyl beta -sulfinylamines derived from aryl, fluoroalkyl and alkyl imines, with clean stereoinversion at carbon. Several 1,2-chloroamines produced via NOCPR were transformed into the corresponding aziridines. (C) 2001 Elsevier Science Ltd. All rights reserved.