N¹-(3,5-bis(trifluoromethyl)phenyl)-N²-(3-hydroxyphenyl)phthalamide | 1615737-65-9

• 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: N¹-(3,5-bis(trifluoromethyl)phenyl)-N²-(3-hydroxyphenyl)phthalamide
• CAS: 1615737-65-9
• 化学式: C₂₂H₁₄F₆N₂O₃
• 分子量: 468.355
• InChiKey: MPPBQMHKZNSIPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.43
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N¹-(3,5-bis(trifluoromethyl)phenyl)-N²-(3-hydroxyphenyl)phthalamide 、 (R)-(1,1′-联萘-2,2′-二氧)氯膦 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到N¹-(3,5-bis(trifluoromethyl)phenyl)-N²-(3-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)phenyl)phthalamide
  参考文献：
  名称：

  Enantioselective synthesis of 1-vinyltetrahydroisoquinolines through palladium-catalysed intramolecular allylic amidation with chiral PhthalaPhos ligands

  摘要：

  The PhthalaPhos ligands, chiral BINOL monophosphites endowed with a phthalamide group, have been screened in the synthesis of 1-vinyltetrahydroisoquinolines by intramolecular palladium-catalysed asymmetric allylic amidation (AAA) of achiral tosylamidocarbonates. Identification of the best ligand followed by optimisation of the reaction conditions allowed the desired product to be obtained with up to 83% ee. Remarkably, the reaction is stereoconvergent, affording the same enantiomer of the desired product regardless of the geometry of the allylic carbonate's double bond, which allows, in principle, the use of E/Z mixtures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.04.018
• 作为产物：
  描述：

  苯酐 在 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 N¹-(3,5-bis(trifluoromethyl)phenyl)-N²-(3-hydroxyphenyl)phthalamide
  参考文献：
  名称：

  Enantioselective synthesis of 1-vinyltetrahydroisoquinolines through palladium-catalysed intramolecular allylic amidation with chiral PhthalaPhos ligands

  摘要：

  The PhthalaPhos ligands, chiral BINOL monophosphites endowed with a phthalamide group, have been screened in the synthesis of 1-vinyltetrahydroisoquinolines by intramolecular palladium-catalysed asymmetric allylic amidation (AAA) of achiral tosylamidocarbonates. Identification of the best ligand followed by optimisation of the reaction conditions allowed the desired product to be obtained with up to 83% ee. Remarkably, the reaction is stereoconvergent, affording the same enantiomer of the desired product regardless of the geometry of the allylic carbonate's double bond, which allows, in principle, the use of E/Z mixtures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.04.018

文献信息

• Synthesis of a 4-Vinyltetrahydrocarbazole by Palladium-Catalyzed Asymmetric Allylic Alkylation of Indole-Containing Allylic Carbonates
  作者：Luca Pignataro、Daniele Fiorito、Vito Vece、Raffaella Ferraccioli、Cesare Gennari

  DOI：10.1002/ejoc.201500979

  日期：2015.10

  phosphite to form the Pd0 catalyst―allowed better and more reproducible results to be obtained relative to the results achieved by using [Pd2(dba)3·CHCl3] (dba = dibenzylideneacetone) and [Pd(allyl)Cl]2. A ligand screening led to identification of the best ligand [(S)-L1], which, after optimization of the reaction parameters, gave product 3 with 75 % ee. Remarkably, the reaction turned out to be stereodivergent:

  钯催化的分子内不对称烯丙基烷基化首次用于制备 4-乙烯基四氢咔唑 3。在由 Pd(OAc)2 和 Pd(OAc)2 原位形成的手性催化剂存在下合成并环化合适的含吲哚烯丙基碳酸酯PhthalaPhos 配体库（即具有邻苯二甲酸二酰胺基团的 1,1'-bi-2-naphthol-monophosphites）。使用稳定且容易获得的钯源，如 Pd(OAc)2——被亚磷酸酯原位还原形成 Pd0 催化剂——相对于使用 [Pd2(dba )3·CHCl3](dba=二亚苄基丙酮)和[Pd(烯丙基)Cl]2。配体筛选确定了最佳配体 [(S)-L1]，在优化反应参数后，得到具有 75% ee 的产物 3。值得注意的是，反应结果是立体发散的：通过使用配体 (S)-L1，发现产物 3 的绝对构型取决于底物双键 [(E)-底物 (S)-3, ( Z)-底物(R)-3]。