3-(3-methoxybenzyl)-1,3-dihydro-2H-indol-2-one

• 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: 3-(3-methoxybenzyl)-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-(3-methoxybenzyl)-1,3-dihydroindol-2-one；3-(3-methoxybenzyl)indolin-2-one；3-[(3-Methoxyphenyl)methyl]-2,3-dihydro-1H-indol-2-one；3-[(3-methoxyphenyl)methyl]-1,3-dihydroindol-2-one
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: HTCZUIWPAZEALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-methoxybenzyl)-1,3-dihydro-2H-indol-2-one 在 C₇₂H₇₂N₈O₆^(2-)*2F₆P^(1-)*2Co⁽³⁺⁾*2C₂H₃O₂^(1-) 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 37.0h， 生成 (R,R)-tert-butyl-3-(3-methoxybenzyl)-3-(-1-(tert-butoxycarbonyl)-2,5-dioxopyrrolidin-3-yl)-2-oxoindolin-1-carboxylate
  参考文献：
  名称：

  多功能双-路易斯-酸/双-三唑鎓催化剂，用于在马来酰亚胺上立体选择性地加成1,2-辛二酮1,4

  摘要：

  在不典型地高酶底物特异性的情况下，实现类似酶的催化活性和立体选择性是开发用于不对称合成的人工催化剂的一个挑战。多官能催化剂被认为是实现优异催化效率的有前途的工具。开发了一种多官能催化剂系统，该系统结合了两个路易斯酸性/布朗斯台德碱性钴中心以及三唑鎓部分，三唑鎓部分对于在将吲哚直接1,4加成到马来酰亚胺中的高反应性和出色的立体选择性至关重要。催化剂通过点击化学进行组装，并且通过利用其装料通过沉淀易于回收。动力学研究支持协同作用方式。

  DOI：

  10.1002/anie.201814453
• 作为产物：
  描述：

  (E)-6-chloro-3-(3-methoxy-benzylidene)-1,3-dihydro-indol-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 30.0 ℃ 、344.75 kPa 条件下， 反应 16.0h， 以84%的产率得到3-(3-methoxybenzyl)-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity

  摘要：

  Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventive potential. To investigate this possibility, we have synthesized and evaluated a series of functionalized 3-benzylidene-indolin-2-ones for induction of NQO1 in murine Hepa1c1c7 cells as well as antiproliferative activity against two human cancer cell lines (MCF-7, HCT116). The benzylideneindolinones were found to be good inducers of NQO1 activity, with 85% of test compounds able to increase basal NQO1 activity by more than twofold at concentrations of <= 10 mu M. By contrast, fewer compounds (11%) tested at the same concentration were able to reduce cell viability by more than 50%. Structure activity relationships showed that the nitrogen linked Michael acceptor moiety was an essential requirement for both activities. This common feature notwithstanding, substitution of the 3-benzylidene-indolin-2-one core structure affected NQO1 induction and antiproliferative activities in dissimilar ways, underscoring different structural requirements for these two activities. Nonetheless, promising compounds ( 10, 42, 45-48) were identified that combine selective induction of NQO1 with potent antiproliferative activity. A potential advantage of such agents would be the ability to provide added protection to normal cells by the up-regulation of NQO1 and other phase II enzymes while simultaneously targeting neoplastic cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.052

文献信息

• Ruthenium-Catalyzed Alkylation of Oxindole with Alcohols
  作者：Thomas Jensen、Robert Madsen

  DOI：10.1021/jo900341w

  日期：2009.5.15

  An atom-economical and solvent-free catalytic procedure for the mono-3-alkylation of oxindole with alcohols is described. The reaction is mediated by the in situ generated catalyst from RuCl3·xH2O and PPh3 in the presence of sodium hydroxide. The reactions proceed in good to excellent yields with a wide range of aromatic, heteroaromatic, and aliphatic alcohols.

  描述了用于羟吲哚与醇的单-3-烷基化的原子经济且无溶剂的催化方法。该反应由RuCl 3 · x H 2 O和PPh 3在氢氧化钠存在下原位生成的催化剂介导。使用多种芳族，杂芳族和脂族醇，反应可以以良好的收率进行，收率很高。
• Transition-Metal-Free C–H Hydroxylation of Carbonyl Compounds
  作者：Moreshwar B. Chaudhari、Yogesh Sutar、Shreyas Malpathak、Anirban Hazra、Boopathy Gnanaprakasam

  DOI：10.1021/acs.orglett.7b01616

  日期：2017.7.7

  and reductant free α-C(sp3)–H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation

  据报道，过渡金属和无还原剂的羰基化合物的α-C（sp3）–H羟基化。此方法由市售的廉价KO- t- Bu和室温下的大气氧化剂作为促进剂。这种统一的策略对于各种羰基化合物衍生物的羟基化以极好的收率获得季羟基化合物也非常容易。初步的机械研究得到了同位素标记和计算研究的支持，表明过氧化物键的形成及其通过原位生成的烯醇盐的裂解。
• New One-Pot Synthesis of 3-Alkyl- and 3-(ψ-Hydroxyalkyl)oxindoles from Isatins
  作者：Balázs Volk、Gyula Simig

  DOI：10.1002/ejoc.200300219

  日期：2003.10

  A new and efficient one-pot procedure has been developed for the synthesis of 3-alkyl- and 3-(ψ-hydroxyalkyl)oxindoles from isatins by treatment with alcohols and diols in the presence of Raney nickel, under hydrogen atmosphere. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  已开发出一种新的高效单锅法，用于在氢气气氛下，在阮内镍存在下，用醇和二醇处理，从靛红合成 3-烷基-和 3-（ψ-羟烷基）羟吲哚。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality
  作者：Jianlin Zhang、Yulong Zhang、Lili Lin、Qian Yao、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c5cc03203b

  日期：——

  The asymmetric Michael addition/desymmetrization reaction catalyzed by a N,N′-dioxide-Sc(iii) complex was realized, leading to the succinimides with two kinds of stereogenic elements—atom chirality and axial chirality in up to 99% yield, 99% ee and >19 : 1 d.r.

  由一个N,N'-二氧化物-Sc(iii)配合物催化的不对称Michael加成/去对称化反应已被实现，导致琥珀酰亚胺产率高达99％，对映异构体纯度为99％，且具有两种立体异构元素 - 原子手性和轴向手性，d.r.> 19:1。
• Regio- and enantioselective conjugate addition of β-nitro α,β-unsaturated carbonyls to construct 3-alkenyl disubstituted oxindoles
  作者：Changli He、Xiaoxue Tang、Xin He、Yuqiao Zhou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.cclet.2022.05.001

  日期：2023.1

  Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to β-nitroenones or β-nitroacrylates was established with chiral scandium catalysts. It enabled the construction of functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups in excellent yields and ee values.

  使用手性钪催化剂建立了3-取代羟吲哚与β-硝基烯酮或β-硝基丙烯酸酯催化不对称共轭加成的区域选择性逆转。它能够以优异的产率和ee值构建官能化的 3,3-二取代羟吲哚，包括末端和内部乙烯基。