tert-butyl 3-[(4-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate | 1229652-47-4

• 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-[(4-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate
• CAS: 1229652-47-4
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: UHRTWPNUCSZHBG-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-[(4-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 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 34.17h， 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
• 作为产物：
  描述：

  在 二氢吡啶 作用下， 以 二氯甲烷 为溶剂， 以86 %的产率得到tert-butyl 3-[(4-methylphenyl)methyl]-2-oxo-3H-indole-1-carboxylate
  参考文献：
  名称：

  Direct organocatalytic transfer hydrogenation and C–H oxidation: high-yielding synthesis of 3-hydroxy-3-alkyloxindoles

  摘要：

  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。

  DOI：

  10.1039/d3ob01264f

文献信息

• Microfluidic Visible‐Light Paternò–Büchi Reaction of Oxindole Enol Ethers
  作者：Pietro Franceschi、Javier Mateos、Alberto Vega‐Peñaloza、Luca Dell'Amico

  DOI：10.1002/ejoc.202001057

  日期：2020.11.22

  From oxindole with flow: Oxindole enol ethers are engaged in microfluidic visible‐light Paternò–Büchi processes, allowing the concomitant C2‐C3 functionalisation of the biorelevant heterocyclic core, in high yield and selectivity.

  从具有流动性的羟吲哚开始：羟吲哚烯醇醚参与了微流体可见光Paternò–Büchi过程，从而以高收率和高选择性将生物相关杂环核心的C2-C3功能化。
• Asymmetric Michael Addition of <i>N</i> ‐Boc‐Protected Oxindoles to Nitroalkenes Catalyzed by a Chiral Secondary Amine
  作者：Chuan Wang、Xuena Yang、Dieter Enders

  DOI：10.1002/chem.201200079

  日期：2012.4.16

  New mission for prolinol ethers: A secondary‐amine‐catalyzed Michael addition of N‐Boc‐protected oxindoles to nitroalkenes through a Brønsted base activation mode has been developed, furnishing the products in excellent yields (88–98 %), diastereoselectivities (d.r.=98:2–>99:1) and high to excellent enantioselectivities (82–>99 % ee; see scheme).

  脯氨醇醚的新任务：开发了通过Brønsted碱活化模式将N -Boc保护的羟吲哚在仲胺催化的Michael加成至硝基烯烃的过程中，提供了优异的收率（88–98％），非对映选择性（dr = 98：2–> 99：1）和高至出色的对映选择性（82–> 99％  ee；请参见方案）。
• 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，
• Highly Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Binaphthyl-Modified Tertiary Amines
  作者：Dae Kim、Hyun Lee、Seung Kang

  DOI：10.1055/s-0030-1260770

  日期：2011.7

  The enantioselective conjugate addition reaction of 3-substituted oxindoles with 1,1-bis(benzenesulfonyl)ethylene by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at C3 position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 99% ee).

  研究了联萘修饰的双功能有机催化剂对 3-取代羟吲哚与 1,1-双（苯磺酰基）乙烯的对映选择性共轭加成反应。相应的迈克尔加合物，在羟吲哚的 C3 位置包含一个四元中心，通常以高产率获得，具有出色的对映选择性（高达 99% ee）。
• Chiral iminophosphoranes organocatalyzed asymmetric hydroxylation of 3-substituted oxindoles with oxaziridines
  作者：Baocheng Li、Zhen-Jiang Xu、Jianwei Han

  DOI：10.1016/j.tetlet.2018.05.018

  日期：2018.6

  Enantioselective hydroxylation of N-protected 3-substituted oxindoles has been developed via chiral iminophosphorane catalysis with oxaziridines as oxidants. As such, a variety of optically active 3-substituted-3-hydroxy-2-oxindoles were obtained in excellent yields (91–99%) and moderate to excellent level of enantiomeric excess (up to 94% ee).

  N-保护的3-取代的羟吲哚的对映选择性羟基化已经通过手性亚氨基正膦催化并以恶二吡啶为氧化剂进行了开发。因此，以优异的收率（91–99％）和中等至出色的对映体过量水平（高达94％ee）获得了各种旋光的3-取代-3-羟基-2-羟基吲哚。