tert-butyl (S)-1-oxo-2-(trifluoromethyl)-2,3-dihydro-1H-indene-2-carboxylate | 1383273-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tert-butyl (S)-1-oxo-2-(trifluoromethyl)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: tert-butyl (2S)-3-oxo-2-(trifluoromethyl)-1H-indene-2-carboxylate
• CAS: 1383273-98-0
• 化学式: C₁₅H₁₅F₃O₃
• 分子量: 300.278
• InChiKey: HOFPOJYNUWWNQO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 在 C₃₃H₂₉F₆N₂O⁽¹⁺⁾*Br^(1-) 、 二正丁基氧化锡 、 caesium carbonate 作用下， 以 氯苯 、 甲苯 、 叔丁醇 为溶剂， 反应 64.0h， 生成 tert-butyl (S)-1-oxo-2-(trifluoromethyl)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters

  摘要：

  The visible-light-driven, phase-transfer-catalyzed, enantioselective perfluoroalkylation and trifluoro-methylation of cyclic beta-ketoesters is described. The photo-organocatalytic process, which occurs at ambient temperature and under visible light illumination, is triggered by the photochemical activity of in situ-generated electron donor-acceptor complexes, arising from the association of chiral enolates and perfluoroalkyl iodides. Preliminary mechanistic studies are reported.

  DOI：

  10.1021/jacs.5b03243

文献信息

• Lanthanum‐Catalyzed Enantioselective Trifluoromethylation by Using an Electrophilic Hypervalent Iodine Reagent
  作者：Albert Granados、Iván Rivilla、Fernando P. Cossío、Adelina Vallribera

  DOI：10.1002/chem.201900598

  日期：2019.6.21

  A highly enantioselective catalytic method for the synthesis of quaternary α‐trifluoromethyl derivatives of 3‐oxo esters is described. The reaction uses lanthanum(III) triflate and chiral PyBOX‐type C2‐symmetric ligands to generate intermediate LaIII complexes that incorporate an enolate moiety of the starting 3‐oxo ester and the trifluoromethylation transfer reagent. The enantioselectivity of the

  描述了一种高对映选择性催化方法，用于合成3-氧代酯的季α-三氟甲基衍生物。该反应使用三氟甲磺酸镧（III）和手性PyBOX型C 2对称配体生成中间体La III配合物，该配合物结合了起始3-氧代酸酯和三氟甲基化转移试剂的烯醇部分。该反应的对映选择性源于一个单元的C 2对称配体对La III烯醇前手性表面之一的有效阻断。
• Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters
  作者：Qing-Hai Deng、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/ja3039773

  日期：2012.7.4

  Enantioselective Cu-catalyzed trifluoromethylation of β-ketoesters using commercially available trifluoromethylating reagents is reported. A number of α-CF(3) β-ketoesters are obtained with up to 99% ee. The trifluoromethylated products were then transformed diastereoselectively to α-CF(3) β-hydroxyesters with two adjacent quaternary stereocenters via a Grignard reaction.

  报道了使用市售三氟甲基化试剂对 β-酮酯进行对映选择性 Cu 催化的三氟甲基化。获得了许多具有高达 99% ee 的 α-CF(3) β-酮酯。然后通过格氏反应将三氟甲基化产物非对映选择性地转化为具有两个相邻季立体中心的 α-CF(3) β-羟基酯。
• Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines
  作者：Shun Noritake、Norio Shibata、Yoshinori Nomura、Yiyong Huang、Andrej Matsnev、Shuichi Nakamura、Takeshi Toru、Dominique Cahard

  DOI：10.1039/b909641h

  日期：——

  Chiral nonracemic guanidines act as Brønsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of β-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60–70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination

  手性非外消旋胍充当布朗斯台德碱，通过以下方法生成β-酮酯的对映选择性亲电子三氟甲基化胍基烯醇盐。 S-（三氟甲基）二苯并噻吩四氟硼酸盐（梅本试剂）具有良好的对映选择性，范围为60–70％。尽管仍然可以改善ee的事实，但这项工作中报道的模型仍可以激发化学家的想象力，以设计新的手性碱来改善立体化学结果。