tert-butyl 3-[(3-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate | 1290606-72-2

• 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 3-[(3-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate
• CAS: 1290606-72-2
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: NKCKSPRBWVLYDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 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：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[(3-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate 在 四丁基溴化铵 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 82.17h， 生成
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2015.10.039

文献信息

• Synthesis, Characterization, and Reactivity of a Hypervalent‐Iodine‐Based Nitrooxylating Reagent
  作者：Roxan Calvo、Antoine Le Tellier、Thomas Nauser、David Rombach、Darryl Nater、Dmitry Katayev

  DOI：10.1002/anie.202005720

  日期：2020.9.21

  synthesis and characterization of a hypervalent‐iodine‐based reagent that enables a direct and selective nitrooxylation of enolizable C−H bonds to access a broad array of organic nitrate esters is reported. This compound is bench stable, easy‐to‐handle, and delivers the nitrooxy (‐ONO2) group under mild reaction conditions. Activation of the reagent by Brønsted and Lewis acids was demonstrated in the synthesis

  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。
• Amino-Indanol-Catalyzed Asymmetric Michael Additions of Oxindoles to Protected 2-Amino-1-nitroethenes for the Synthesis of 3,3′-Disubstituted Oxindoles Bearing α,β-Diamino Functionality
  作者：Xiong-Li Liu、Zhi-Jun Wu、Xi-Lin Du、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/jo2004378

  日期：2011.5.20

  An organocatalytic asymmetric Michael addition reaction of 3-substituted oxindoles to protected 2-amino-1-nitroethenes has been developed. The reaction is catalyzed by a simple and readily available amino-indanol derivative and affords the desired products in very high yields (up to 99%) with excellent diastereoselectivities (up to >99:1) and very good enantioselectivities (up to 90%). Significantly

  已经开发出3-取代的羟吲哚与被保护的2-氨基-1-硝基乙烯的有机催化不对称迈克尔加成反应。该反应由一种简单易得的氨基氨基茚满醇衍生物催化，以非常高的非对映选择性（高达> 99：1）和非常好的对映选择性（高达90％）以非常高的收率（高达99％）提供所需的产物。 。重要的是，这项研究为构建带有α，β-二氨基官能团的3，3′-二取代的羟吲哚以及邻近的手性季/叔立体中心提供了一种通用的催化方法。该协议的潜在效用也已通过克级反应和产物的多用途转化得到了证明。此外，根据全面的实验结果和其中一种迈克尔加合物的绝对构型，
• Organocatalytic Asymmetric Conjugate Addition of 3-Monosubstituted Oxindoles to (<i>E</i>)-1,4-Diaryl-2-buten-1,4-diones: A Strategy for the Indirect Enantioselective Furanylation and Pyrrolylation of 3-Alkyloxindoles
  作者：Yu-Hua Liao、Xiong-Li Liu、Zhi-Jun Wu、Xi-Lin Du、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1002/chem.201103293

  日期：2012.5.21

  3′‐disubstituted oxindoles—3‐furanyl‐ and 3‐pyrrolyl‐3‐alkyl‐oxindoles—in high yields and good enantioselectivities. Notably, the studies presented here sufficiently confirm that this two‐step strategy of sequential conjugate addition/Paal–Knorr cyclization is not only an attractive method for the indirect enantioselective heteroarylation of 3‐alkyloxindoles, but also opens up new avenues toward asymmetric synthesis

  3-单取代的羟吲哚的不对称共轭加成范围为（E）描述了由市售的辛可宁催化的1,4-二芳基-2-丁烯-1,4-二酮。这种有机催化不对称反应提供了范围广的3,3'-二取代的羟吲哚，这些化合物包含1,4-二羰基部分以及附近的季铵和叔立体中心，收率高至优异（高达98％），并具有出色的非对映异构体和中高对映体比例（分别高达99：1和95：5）。随后，在不同的Paal–Knorr条件下，所得迈克尔加合物中1,4-二羰基部分的环化产生了两种新型的3,3'-二取代的羟吲哚——3-呋喃基和3-吡咯基-3-烷基-氧吲哚-高收率和良好的对映选择性。尤其，
• Asymmetric tandem conjugate addition–protonation to forge chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position
  作者：San-Ni Hong、Yang Liu、Richmond Lee、Zhiyong Jiang

  DOI：10.1039/c7cc03700g

  日期：——

  strategy to construct chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position is described. Methylene 1,3-oxazolidine-2,4-diones were for the first time employed in an asymmetric reaction as viable electrophiles undergoing a tandem conjugate addition–protonation process. Using an L-amino acid-based urea–tertiary amine catalyst, the reaction with 3-substituted oxindoles

  描述了在不相邻的β位置上为季碳立体中心构建手性二级C-O键的直接策略。亚甲基1,3-恶唑烷-2,4-二酮首次在不对称反应中用作活泼的亲电子试剂，经历了串联共轭加成-质子化过程。使用基于L-氨基酸的脲-叔胺催化剂，与3-取代的羟吲哚的反应可制得有价值的质子化加合物，具有1,3-季-叔（C-O）不相邻的立体中心，并具有高收率和出色的立体选择性。该方法已成功地推广到硫亲核试剂上，用于合成具有生物活性的手性1，3-硫叔叔醇衍生物。
• Asymmetric direct α-alkylation of 2-oxindoles with Michler's hydrol catalyzed by bis-cinchona alkaloid–Brønsted acid via an SN1-type pathway
  作者：Tao Zhang、Zhen Qiao、Yan Wang、Nengjun Zhong、Li Liu、Dong Wang、Yong-Jun Chen

  DOI：10.1039/c3cc39012h

  日期：——

  An enantioselective direct α-alkylation of 2-oxindoles with Michler's hydrol via an SN1-type pathway in the non-covalent activation mode using the bis-cinchona alkaloid and Brønsted acid as a co-catalyst was developed and good to high yields and enantioselectivities were obtained.

  以双金鸡纳生物碱和 Br¸nsted 酸为助催化剂，在非共价活化模式下，通过 SN1 型途径开发了 2-oxindoles 与 Michler's hydrol 的直接δ-烷基化对映体选择性反应，并获得了很高的产率和对映体选择性。