N-(3,5-dimethylbenzyl)isatin | 1178327-20-2

• 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: N-(3,5-dimethylbenzyl)isatin
• 英文别名: 1-[(3,5-Dimethylphenyl)methyl]indole-2,3-dione
• CAS: 1178327-20-2
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: GMRULDKHUTXONW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3,5-dimethylbenzyl)isatin 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium carbonate 、 caesium carbonate 、 双(2-二苯基磷苯基)醚 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  两性离子π-炔丙基钯物种实现的亚甲基亚吲哚啉酮与钯催化的亚乙烯基环丙烷-二酯的发散环加成反应

  摘要：

  公开了通过亚乙烯基亚环丙烷-二酯与亚甲基吲哚满酮的环加成反应，钯与五元或六元环稠合的螺硫醇的发散合成。该协议的特点是在环加成反应中原位生成的前所未有的两性离子π-炔丙基钯物种以及通过改变膦配体在（3 + 2）和（4 + 2）环加成之间可切换的过程。

  DOI：

  10.1039/d1cc01453f
• 作为产物：
  描述：

  3,5-二甲基溴苄 、 靛红 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3,5-dimethylbenzyl)isatin
  参考文献：
  名称：

  通过Morita-Baylis-Hillman反应构建手性季碳：对3-取代的3-羟基羟吲哚衍生物的对映选择性方法

  摘要：

  已经证明了一种新的对映选择性方法，该方法通过催化不对称Morita-Baylis-Hillman反应获得在羟吲哚C3位置的四取代手性中心。该反应可提供3-取代的3-羟基-2-氧吲哚，其收率和ee值都非常好，并且可以很容易地转化为药学上更有趣的化合物。

  DOI：

  10.1002/chem.201002240

文献信息

• Asymmetric Allylation by Chiral Organocatalyst‐Promoted Formal Hetero‐Ene Reactions of Alkylgold Intermediates
  作者：Guizhi Dong、Ming Bao、Xiongda Xie、Shikun Jia、Wenhao Hu、Xinfang Xu

  DOI：10.1002/anie.202012678

  日期：2021.1.25

  form, and which are otherwise impossible to access. Mechanistic evidence reveals the presence of an alkylgold intermediate, and an X‐ray crystal structure of the allylgold species illuminates its unique stability and reactivity. An asymmetric formal hetero‐ene reaction of this gold intermediate, involving a dearomatization process, is enabled with assistance of a quinine‐derived squaramide catalyst. This

  据报道，金和手性有机催化剂的协同催化策略可实现前所未有的伊斯汀和伊斯汀衍生的酮亚胺催化不对称烯丙基化反应。此方法可快速访问主要包含光学纯净形式的，包含邻位立体异构中心的手性2,5-二取代的亚烷基恶唑啉，否则无法访问。机理证据表明存在烷基金中间体，烯丙基金物种的X射线晶体结构阐明了其独特的稳定性和反应性。在奎宁衍生的方酰胺催化剂的辅助下，该金中间体的不对称形式的杂烯反应涉及脱芳香化过程。这一新发现扩展了金络合物的合成应用和金催化的多功能性。
• Facile and Convenient Synthesis of Functionalized Aryl-Containing Isoindigo Derivatives via Substituted Indolin-2-one Carbene Dimerization
  作者：Andrei V. Bogdanov、Vladimir F. Mironov、Lenar I. Musin、Rashid Z. Musin、Dmitry B. Krivolapov、Igor A. Litvinov

  DOI：10.1080/00397911.2011.558232

  日期：2012.8.15

  reaction of substituted benzyl-, aroylmethyl-, or 1-phenetylisatins with hexaethyltriaminophosphine has been shown to lead to the formation of a library of 3,3′-biindolinylidene-2,2′-diones with functionalized benzyl-, aroylmethyl-, and 1-phenetyl fragments at the nitrogen atom. GRAPHICAL ABSTRACT

  摘要 取代的苄基-、芳酰基甲基-或 1- 苯基染色素与六乙基三氨基膦的反应已被证明可形成 3,3'-二二吲哚亚基-2,2'-二酮与功能化的苄基-、芳酰基甲基-、和氮原子上的 1-苯基碎片。图形概要
• ChCl:Urea deep eutectic solvent as a green media for one-pot, three-component catalyst-free synthesis of spiro-benzoxazole derivatives
  作者：Fatemeh Asilpour、Dariush Saberi、Alireza Hasaninejad

  DOI：10.1016/j.molliq.2024.125537

  日期：2024.9

  An efficient catalyst-free procedure is reported for the one-pot three-component synthesis of novel spiro-benzoxazole derivatives via the condensation reaction of isatins, dihydrobenzoxazole compounds, and malono derivatives in ChCl:Urea deep eutectic solvent, as a green reaction medium. Spiro-benzoxazoles were easily extracted from the reaction mixture, by adding water, and isolated in good to excellent

  报道了一种高效的无催化剂程序，用于通过菖蒲素、二氢苯并恶唑化合物和马洛诺衍生物在 ChCl：尿素 深共熔溶剂中作为绿色反应介质进行一锅法三组分合成新型螺并恶唑衍生物。通过加水，很容易从反应混合物中提取螺-苯并恶唑，并以良好到极好的产量分离。
• X-ray crystallographic study of diversely substituted isatin derivatives
  作者：E.V. Mironova、A.V. Bogdanov、D.B. Krivolapov、L.I. Musin、I.A. Litvinov、V.F. Mironov

  DOI：10.1016/j.molstruc.2014.09.021

  日期：2015.1

  A series of isatin derivatives were synthesized and studied by XRD. For the first time the peculiarities of the molecule structure and crystal packing effects were analyzed. Indoline heterocycles are planar in all the investigated structures. The molecules bearing the sterically hindered substituents at nitrogen atom of indoline heterocycle have the maximum deviations of two oxygen atoms from the indoline plane. The substituent nature at nitrogen atom does not effect on the bond lengths of indoline moiety. The value of endocyclic bond angle at nitrogen not so strongly depends on the substituent and is almost equal to the one in unsubstituted isatin. In contrast to the unsubstituted isatin, where the system of classical hydrogen N-H center dot center dot center dot O-bonds is realized, in crystals of investigated compounds there is no opportunity to reveal ones, and the crystal structure is stabilized by C-H center dot center dot center dot O- and pi-pi-interactions. (C) 2014 Elsevier B.V. All rights reserved.
• Asymmetric [4+2] Annulations of Isatins with But-3-yn-2-one
  作者：Qiang Wang、Zhong Lian、Qin Xu、Min Shi

  DOI：10.1002/adsc.201300583

  日期：2013.11.25

  AbstractThe catalytic asymmetric [4+2] annulations of isatins with but‐3‐yn‐2‐one catalyzed by the Cinchona alkaloids‐derived oragnocatalyst (DHQD)2PHAL have been developed in the presence of 3.0 equivalents of D‐diethyl tartrate in the mixed solvent (diphenyl ether/diethyl ether=1/1) or a slightly modified one, affording the corresponding substituted spiro[indoline‐3,2′‐pyran]‐2,4′(3′H)‐diones in good to excellent yields with high enantioselectivities under mild conditions.magnified image