3-叔丁基羰基氨基-3-(4-叔丁基苯酚)-丙酸 | 185198-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-叔丁基羰基氨基-3-(4-叔丁基苯酚)-丙酸
• 英文名称: trifluoromethanesulfonic acid 8-phenylsulfonyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl ester
• 英文别名: 8-benzenesulfonyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate；[8-(benzenesulfonyl)-5-oxo-2,3-dihydro-1H-indolizin-6-yl] trifluoromethanesulfonate
• CAS: 185198-44-1
• 化学式: C₁₅H₁₂F₃NO₆S₂
• 分子量: 423.391
• InChiKey: KBYLVPLHYXIRBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-叔丁基羰基氨基-3-(4-叔丁基苯酚)-丙酸 在 甲酸 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到8-phenylsulfonyl-2,3-dihydro-1H-indolizin-5-one
  参考文献：
  名称：

  An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones

  摘要：

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.

  DOI：

  10.1021/jo9911600
• 作为产物：
  描述：

  1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 在 rhodium⁽²⁺⁾ 三乙胺 作用下， 生成 3-叔丁基羰基氨基-3-(4-叔丁基苯酚)-丙酸
  参考文献：
  名称：

  1,3-偶极环加成化学用于制备基于吲哚嗪酮的新型化合物

  摘要：

  由5-（氧代-6）-三氟甲磺酰氧基-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯开始，通过Rh（II）催化的1-（2-苯磺酰基-2）的1,3-偶极环加成反应获得（重氮基乙酰基）吡咯烷-2-酮和丙烯酸甲酯，可有效制备几种吲哚和呋喃并熔的吲哚并酮。在第一种情况下，三氟甲磺酸酯与各种取代的苯胺的钯介导的C-N偶联提供了所需的5-氧代-6-（芳基氨基）-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯高产。6-（2-溴苯基氨基）-5-氧-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯及其脱羧类似物6-（2-溴苯基氨基）-2,3-二氢-1 H-吲哚izin-5-one，以极高的产率合成，并经过分子内Heck环化反应，得到1,2,3,6-tetrahydroindolizino [6,7- b ] indol-5-ones。为了制备呋喃并稠合的吲哚嗪酮，将6-羟基-5-氧代-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯与不

  DOI：

  10.1021/jo0511492

文献信息

• A New β-Carbolinone Synthesis Using a Rh(II)-Promoted [3 + 2]-Cycloaddition and Pd(0) Cross-Coupling/Heck Cyclization Chemistry
  作者：Joel M. Harris、Albert Padwa

  DOI：10.1021/ol0356338

  日期：2003.10.1

  [reaction: see text]. A short and efficient synthesis of the beta-carbolinone ring system was achieved using a rhodium(II)-catalyzed [3 + 2]-cycloaddition, a Pd(0)-catalyzed C-N amination reaction, and a subsequent intramolecular Heck reaction as the key synthetic steps.

  [反应：请参见文字]。使用铑（II）催化的[3 + 2]-环加成反应，Pd（0）催化的CN胺化反应和随后的分子内Heck反应，可以实现β-咔啉酮环系统的短而有效的合成综合步骤。
• Pyridinones to treat and prevent bacterial infections
  申请人：Almqvist Frederic

  公开号：US06841559B1

  公开（公告）日：2005-01-11

  Novel pyridinones and their derivatives which are effective in treating or preventing Gram-negative bacterial infections are provided. The pyridinones are stable and easily derivatized; the methods by which these derivatizations occur is described. Two regioselective and functional group tolerant methods for the synthesis of the novel pyridinones are also provided. One such synthetic method involves reacting an imine and a Meldrum's acid derivative in solution. The other synthetic method is a solid phase synthesis of the pyridinones in which an imine is prepared bound to a solid support and a Meldrum's acid derivative is reacted with the imine. Novel imine intermediates useful in the solid phase and solution methods of synthesizing the pyridionones are also described.

  提供了一种治疗或预防革兰氏阴性细菌感染的新型吡啶酮及其衍生物。这些吡啶酮稳定且易于衍生化；描述了这些衍生化发生的方法。还提供了两种选择性区域和功能基容忍的合成新型吡啶酮的方法。其中一种合成方法涉及在溶液中反应亚胺和梅尔德鲁姆酸衍生物。另一种合成方法是吡啶酮的固相合成，其中亚胺被制备成固定在固体支持物上，然后梅尔德鲁姆酸衍生物与亚胺反应。还描述了在合成吡啶酮的固相和溶液方法中有用的新型亚胺中间体。
• New Synthetic Route to 2-Pyridones and Its Application toward the Synthesis of (±)-Ipalbidine
  作者：Scott M. Sheehan、Albert Padwa

  DOI：10.1021/jo961690l

  日期：1997.2.1
• PYRIDINONES TO TREAT AND PREVENT BACTERIAL INFECTIONS
  申请人：WASHINGTON UNIVERSITY

  公开号：EP1233967A1

  公开（公告）日：2002-08-28
• EP1233967A4
  申请人：——

  公开号：EP1233967A4

  公开（公告）日：2003-07-09