tert-butyl 2-oxo-3-[[4-(trifluoromethyl)phenyl]methyl]-3H-indole-1-carboxylate | 1351305-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 2-oxo-3-[[4-(trifluoromethyl)phenyl]methyl]-3H-indole-1-carboxylate
• CAS: 1351305-87-7
• 化学式: C₂₁H₂₀F₃NO₃
• 分子量: 391.39
• InChiKey: BABVLPGXXOYKMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-oxo-3-[[4-(trifluoromethyl)phenyl]methyl]-3H-indole-1-carboxylate 在 zinc perchlorate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 30.0h， 生成 (R)-ethyl 2-acetoxy-2-((R)-2-oxo-3-(4-(trifluoromethyl)benzyl)indolin-3-yl)acetate
  参考文献：
  名称：

  N -Boc-Oxindoles与聚合乙醛酸乙酯的金鸡纳生物碱催化对映选择性直接羟醛反应

  摘要：

  提出了N -Boc-羟吲哚向聚合乙醛酸乙酯的第一次对映选择性直接羟醛加成。该反应通过使用低至0.1 mol％（DHQ）2 PHAL的方法进行，并获得带有相邻仲醇和季立体中心的α-羟基羧酸酯衍生物，且非对映和对映体控制水平较高。聚合形式的乙醛酸乙酯的使用代表了合成应用的重要优势，并允许我们直接安装C 2单元，准备将其转化为有用的结构单元。由锌（CLO催化进一步的一锅煮保护/去保护序列4）2 ⋅6ħ 2O通过寄生醇催化的逆向醇醛缩合反应保留了α-羟基羧酸盐不受消旋作用。

  DOI：

  10.1002/adsc.201100499
• 作为产物：
  描述：

  4-(三氟甲基)苄醇 在 ruthenium(III) chloride trihydrate 、 sodium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 2-oxo-3-[[4-(trifluoromethyl)phenyl]methyl]-3H-indole-1-carboxylate
  参考文献：
  名称：

  基于高碘的硝基氧化试剂的合成，表征和反应性。

  摘要：

  本文报道了一种基于高价碘的试剂的合成和表征，该试剂能够使可烯醇化的CH键进行直接和选择性的硝基氧化，从而获得广泛的有机硝酸酯。该化合物在工作台上稳定，易于处理，并能释放出硝基氧基（-ONO 2）组在温和的反应条件下。在硝基氧化的β-酮酸酯，1,3-二酮和丙二酸酯的合成中证明了Brønsted和Lewis酸对试剂的激活，而在硝基氧化的吲哚的合成中则显示了其在光氧化还原催化下的活性。详细的机理研究包括脉冲辐解，斯特恩-沃尔默淬灭研究和UV / Vis光谱电化学，揭示了一种独特的单电子转移（SET）诱导的协同机理，与硝酸根自由基的产生无关。

  DOI：

  10.1002/anie.202005720

文献信息

• Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles via direct gamma-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles
  作者：Ting-Ting Feng、Xuan Huang、Xiong-Li Liu、De-Hong Jing、Xiong-Wei Liu、Feng-Ming Guo、Ying Zhou、Wei-Cheng Yuan

  DOI：10.1039/c4ob01523a

  日期：——

  The first phase transfer-catalysed direct γ-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles has been developed, which affords 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles in up to 83% yield under mild reaction conditions. Furthermore, their biological activity has been preliminarily demonstrated by in vitro evaluation against human prostate cancer

  已经开发出第一批经相转移催化的森田的Bayes-Hillman碳酸异丁酯碳酸酯与3-取代的羟吲哚的直接γ取代反应，该化合物可提供高达83％的3-烯基-羟吲哚环稠合的3,3'-二取代的羟吲哚。在温和的反应条件下收率。此外，使用基于MTT的检测方法，以市售标准药物顺铂为阳性对照，通过针对人前列腺癌细胞PC-3和人白血病细胞K562的体外评估，初步证明了其生物学活性。令人欣慰的是，化合物3aa，3ba和3ca对人前列腺癌细胞（PC-3）的体外抑制活性与顺铂相当。更重要的是，3ba对人白血病细胞K562也具有良好的抑制作用。这些结果表明3-烯基-羟吲哚环稠合的3，3′-二取代的羟吲哚类似物可能是用于进一步生物学筛选的潜在先导化合物。
• Bicyclic guanidinium-catalyzed enantioselective phase-transfer alkylation: direct access to pyrroloindolines and furoindolines
  作者：Wenchao Chen、Wenguo Yang、Lin Yan、Choon-Hong Tan、Zhiyong Jiang

  DOI：10.1039/c3cc46111d

  日期：——

  Highly enantioselective phase-transfer alkylation of 3-substituted-2-oxindoles with activated bromomethanes is disclosed with a broad substrate scope by using bicyclic guanidinium as a catalyst and a Lewis acid as the co-catalyst. The alkylation adducts are versatile intermediates to accomplish the syntheses of pyrroloindolines and furoindolines.

  本发明以双环胍为催化剂，以路易斯酸为助催化剂，实现了 3-取代-2-氧吲哚与活化溴甲烷的高对映选择性相转移烷基化反应，具有广泛的底物范围。烷基化加合物是完成吡咯吲哚和呋喃吲哚合成的多功能中间体。
• Enantioselective Nucleophilic Vinylic Substitution (S_NV) toward 3-Alkenyl-bisoxindoles Facilitated by C6′ Steric Bulk of Cinchona Alkaloid
  作者：Xingyue Wang、Guishun Bai、Ruoqi Liu、Xiaoli Zhu、Xinyi Ye、Tao Zhang、Kui Zhang、Damien Bonne、Jean Rodriguez、Hong Wang、Xiaoze Bao

  DOI：10.1021/acs.orglett.3c01964

  日期：2023.8.18

  A C6′ bulky substituted quinine-catalyzed SNV reaction between 3-substituted oxindole and (E)-3-(nitromethylene)-oxindole was developed. This enantioselective C(sp3)–C(sp2) coupling furnished bisoxindole scaffolds featuring a vinyl-substituted all-carbon quaternary stereocenter with high stereoselectivities. In addition, the gram-scale synthesis and synthetic post-transformations were conducted to

  开发了3-取代的羟吲哚和 ( E )-3-(硝基亚甲基)-羟吲哚之间的C6' 大取代奎宁催化的 SNV反应。这种对映选择性 C( sp 3 )–C( sp 2 ) 偶联提供了具有高立体选择性的乙烯基取代全碳四元立构中心的双氧吲哚支架。此外，还进行了克级合成和合成后转化以证明潜在的合成用途。
• Direct organocatalytic transfer hydrogenation and C–H oxidation: high-yielding synthesis of 3-hydroxy-3-alkyloxindoles
  作者：Pritam Roy、S. Rehana Anjum、Shyam D. Sanwal、Dhevalapally B. Ramachary

  DOI：10.1039/d3ob01264f

  日期：——

  A two-step, high-yielding transfer hydrogenation/C–H oxidation protocol has been developed for the synthesis of 3-alkyl-3-hydroxyoxindoles and medicinally important 3-cyanomethyl-3-hydroxyoxindole, and formal total synthesis of (±)-alline and (±)-CPC-I.

  我们开发了一种两步高产转移氢化/C-H 氧化方案，用于合成 3-烷基-3-羟基吲哚和具有重要药用价值的 3-氰甲基-3-羟基吲哚，以及 (±)-alline 和 (±)-CPC-I 的正式全合成。
• A facile and efficient synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process
  作者：Xiong-Li Liu、Wen-Hui Zhang、Zhen Yao、Xiong-Wei Liu、Li-Jun Peng、Zhi Zhao、Yi Lu、Ying Zhou、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2015.10.039

  日期：2015.12

  A new methodology was developed for the synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process. A wide variety of products bearing a hexahydro-1H-pyrido[2,3-b]indol-2-one core with varying degrees of substitution around it, which is a key structural skeleton found in a large number of biologically active natural products and pharmaceutical compounds, were obtained smoothly with high efficiency (up to overall yield of 67%). Furthermore, their biological activities have been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3, human lung cancer cells A549 and human leukemia cells k562 by the MU-based assays, using the commercially available standard drug Cisplatin as a positive control. These results suggested there is a trend that lipophilic groups improve the potency, and also suggested a carbonyl moiety located in the hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds is beneficial for the activity. The results also demonstrated that most of the compounds showed considerable cytotoxicities to these three cell lines K562, A549 and PC-3, and that hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds may be potential leads for further antitumor activity screenings. (C) 2015 Elsevier Ltd. All rights reserved.