3-hydroxy-3-(2-oxocycloheptyl)indolin-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-hydroxy-3-(2-oxocycloheptyl)indolin-2-one
• 英文别名: 3-hydroxy-3-(2-oxocycloheptyl)-1H-indol-2-one
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: WRDAYOGORAQJTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 环庚酮 在 C₄₂H₇₀O₃₅*C₁₄H₁₉NO₅ 作用下， 以 水 为溶剂， 反应 48.0h， 以98%的产率得到3-hydroxy-3-(2-oxocycloheptyl)indolin-2-one
  参考文献：
  名称：

  超声辅助的基于d-氨基葡萄糖的β-CD包合物的合成及其在水多相有机催化体系中的应用。

  摘要：

  首次为非对称催化应用在基于碳水化合物的分子和β-环糊精（CD）疏水腔之间构建了一种包合物。这种新颖的基于d-氨基葡萄糖的包合物已经通过创新和熟练的空化技术高收率合成，并通过各种技术进行了很好的表征，例如红外光谱，核磁共振光谱，紫外可见光谱，热重分析，扫描电子显微镜和其他光谱技术。据观察，包含一个的d-氨基葡萄糖衍生物进入β-CD的疏水腔增加了其表面积和热稳定性。该催化体系在水中直接进行羟醛缩合反应时​​效果很好，以高收率和非对映选择性和对映选择性提供了优异的收率。

  DOI：

  10.1021/acs.joc.0c00420

文献信息

• Development of <i>C</i>₂-Symmetric Chiral Bifunctional Triamines: Synthesis and Application in Asymmetric Organocatalysis
  作者：Santiago Cañellas、Pedro Alonso、Miquel À. Pericàs

  DOI：10.1021/acs.orglett.8b01957

  日期：2018.8.17

  The synthesis and application of a newly designed C2-symmetric chiral bifunctional triamine family (C2-CBT) is reported. These enantiopure chiral triamine scaffolds can be accessed in multigram amounts from simple amino acids while avoiding chromatographic purification. As a proof of principle, C2-CBT has been studied in the aldol reaction of cyclic ketones with isatins, with the target tertiary alcohols

  报道了新设计的C 2对称手性双官能三胺三胺家族（C 2 -CBT）的合成和应用。这些对映体纯的手性三胺支架可以从简单氨基酸中以数克的量获得，同时避免色谱纯化。作为原理的证明，已经在环状酮与靛红的醛醇缩合反应中研究了C 2 -CBT，并以高效的方式形成了目标叔醇。已经通过简单的提取技术回收了催化剂，并随后进行了再利用。
• Potential Anticonvulsants VI: Condensation of Isatins with Cyclohexanone and other Cyclic Ketones
  作者：Hossein Pajouhesh、Randy Parson、Frank D. Popp

  DOI：10.1002/jps.2600720330

  日期：1983.3

  Abstract □ Cyclohexanone, substituted cyclohexanones, and other cycloalkanones have been condensed with isatin and substituted isatins to give a series of new 3-hydroxy-3-substituted oxindoles. A number of these 3-hydroxyoxindoles possess anticonvulsant activity.

  摘要□环己酮，取代的环己酮和其他环烷酮已与Isatin和取代的Isatins缩合，制得一系列新的3-羟基-3-取代的羟吲哚。这些3-羟基羟吲哚中的许多具有抗惊厥活性。
• <i>In Situ</i>Formed Bifunctional Primary Amine-Imine Catalyst: Application to the Construction of Chiral Tertiary Alcohols through Asymmetric Aldol-Type Reaction
  作者：Zhijie Mao、Xi Zhu、Aijun Lin、Weipeng Li、Yan Shi、Haibin Mao、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/adsc.201300108

  日期：2013.7.8

  An in situ formation method to obtain chiral bifunctional primary amine‐imine catalysts from the C2‐symmetric chiral diimines has been developed. The efficiency of this method in the construction of chiral tertiary alcohols which are valuable pharmaceutical intermediates is proved by its application to the asymmetric aldol‐type reaction of cyclic ketones with other activated ketone compounds as the

  一个原位形成方法从获得的手性双官能伯胺-亚胺催化剂Ç 2 -对称的手性二亚胺已经研制成功。通过将该方法用于环状酮与其他活化酮化合物作为烯胺受体（即β，γ-不饱和α）的不对称醛醇型反应，证明了该方法在构建有价值的医药中间体手性叔醇中的有效性。 -酮酸酯和靛红。通常，具有良好的非对映选择性和对映选择性（β，γ-不饱和α-酮酸酯的最高96/4 dr，96％ee，以及91/9 dr的最高94 / ee，94％ee（对于isatins）。通过ESI-MS分析可以证明反应过程中的伯胺-亚胺的催化活性和烯胺中间体的活性。
• Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
  作者：Giacomo Filippini、Francesco Amato、Cristian Rosso、Giulio Ragazzon、Alberto Vega-Peñaloza、Xavier Companyó、Luca Dell’Amico、Marcella Bonchio、Maurizio Prato

  DOI：10.1016/j.chempr.2020.08.009

  日期：2020.11

  Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory of the surface reactive groups of amine-rich carbon dots (NCDs-1). As a result, NCDs-1 provide a multi-functional nano-platform that is able to covalently activate carbonyl groups, form iminium-ions and enamine intermediates, and efficiently promote diverse aminocatalytic transformations in water. Remarkably, the catalytic activity of carbon dots can also govern the stereoselectivity in the bond-forming event. Indeed, the use of chiral carbon dots (NCDs-7) as catalysts affords the final aldol products with significant enantiomeric excess. The successful implementation of carbon nanostructures into chemical roles so far restricted to molecular systems opens new avenues for advanced applications where the nanoscale and the molecular realms will merge and complement each other.
• 2-Azanorbornane-based amine organocatalyst for enantioselective aldol reaction of isatins with ketones
  作者：Ayumi Ogasawara、U.V. Subba Reddy、Chigusa Seki、Yuko Okuyama、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1016/j.tetasy.2016.08.013

  日期：2016.11

  Optically active 2-azanorbornane-based organocatalysts were designed and synthesized, and the catalytic activity of these catalysts in enantioselective aldol reactions of isatins with ketones was investigated. Among these catalysts, 2-azanorbornylmethanol showed the best catalytic activity to afford the corresponding aldol product in excellent chemical yield (up to 95%) and with moderate stereoselectivity (up to 64% ee, up to syn:anti = 36:64). (C) 2016 Elsevier Ltd. All rights reserved.