tert-butyl (1-benzyl-2-oxo-7-(trifluoromethyl)indolin-3-ylidene)carbamate | 1426931-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (1-benzyl-2-oxo-7-(trifluoromethyl)indolin-3-ylidene)carbamate
• CAS: 1426931-88-5
• 化学式: C₂₁H₁₉F₃N₂O₃
• 分子量: 404.389
• InChiKey: NKAYREKQFGVVGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-benzyl-2-oxo-7-(trifluoromethyl)indolin-3-ylidene)carbamate 在 3-[[（（1R，2R）-2-（1-哌啶基）环己基]氨基]-4-[[4-（三氟甲基）苯基]氨基]-3-环丁烯-1,2-二酮 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以89%的产率得到tert-butyl N-[(3S)-1-benzyl-3-hydroperoxy-2-oxo-7-(trifluoromethyl)indol-3-yl]carbamate
  参考文献：
  名称：

  Asymmetric Catalytic 1,2-Hydroperoxidation of Isatin-Derived Ketimine with Hydrogen Peroxide in the Crowding Environment of PEGs

  摘要：

  The first enantioselective catalytic 1,2-hydroperoxidation has been achieved in the presence of PEG-600 using an acid base bifunctional chiral squaramide as the organocatalyst, affording a range of enantioenriched alpha-N-substituted hydroperoxides bearing an oxindole moiety with excellent stereoselectivities (up to 99% ee).

  DOI：

  10.1021/acs.orglett.7b00032
• 作为产物：
  描述：

  N-benzyl-7-trifluoromethylisatin 、 alkaline earth salt of/the/ methylsulfuric acid 以 1,4-二氧六环 为溶剂， 生成 tert-butyl (1-benzyl-2-oxo-7-(trifluoromethyl)indolin-3-ylidene)carbamate
  参考文献：
  名称：

  用于合成具有手性季碳中心的 3-取代-3-氨基吲哚的不对称催化 aza-Morita-Baylis-Hillman 反应†

  摘要：

  已经通过使用手性氨基和膦基催化剂建立了靛红衍生的酮亚胺与 MVK的不对称催化aza -Morita-Baylis-Hillman ( aza -MBH) 反应。该反应产生了生物医学上重要的 3-取代 3-氨基-2-羟吲哚，收率良好（大多数情况下>80%）和优异的对映选择性（90-99% ee）。已在方便的系统下检查了 28 个由手性四元立体中心组装的病例。

  DOI：

  10.1039/c3ob27495k

文献信息

• An L-tert-leucine derived urea catalyzed asymmetric synthesis of acylclic N, N′-ketals derived from aryl amines and isatin-derived ketimines
  作者：Shuo Liu、Jingdong Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1016/j.tet.2021.132206

  日期：2022.1

  An asymmetric synthesis of N,N′-ketal compounds derived from isatin-derived ketimines and aryl amines has been developed using an inexpensive and readily available L-tert-leucine derived urea catalyst. Using this asymmetric catalytic synthetic method, a series of 3-substituted 3-amino-2-oxoindole derivatives containing an N,N′-ketal motif were obtained in high yields with high enantioselectivities

  已经使用廉价且容易获得的L-叔亮氨酸衍生尿素催化剂开发了衍生自靛红衍生的酮亚胺和芳胺的N,N'-缩酮化合物的不对称合成。使用这种不对称催化合成方法，以高产率和高对映选择性获得了一系列含有N,N'-缩酮基序的 3-取代 3-氨基-2-氧代吲哚衍生物。
• 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。
• Highly Enantioselective Synthesis of Acyclic <i>N</i>,<i>N</i>′-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines
  作者：Yuxin Liu、Jingdong Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1021/acs.orglett.9b02098

  日期：2019.7.19

  N,N′-Acetals are sensitive compounds, and the challenging asymmetric synthesis of acyclic N,N′-acetals by the general addition of amines to ketimines has never been reported so far. In this study, highly enantioselective addition of aryl amines to isatin-derived ketimines catalyzed by chiral urea derived from quinine was developed. A series of new acyclic N,N′-acetals were constructed by this protocol

  N，N'-缩醛是敏感化合物，迄今为止尚未报道过通过向酮亚胺中一般添加胺来挑战性地合成无环N，N'-缩醛的挑战性。在这项研究中，开发了由对苯二酚衍生的手性尿素催化的对映体衍生的酮亚胺中高度对映体选择性的芳基胺加成反应。通过该方案，以高至优异的收率（78–99％）和高至优异的对映选择性（76–96％ee）构建了一系列新的无环N，N'-乙缩醛。
• Copper/guanidine-catalyzed asymmetric alkynylation of isatin-derived ketimines
  作者：Quangang Chen、Lihua Xie、Zhaojing Li、Yu Tang、Peng Zhao、Lili Lin、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/c7cc08920a

  日期：——

  Isatin-derived ketimines undergo enantioselective alkynylation reactions in the presence of copper iodide and easily accessible guanidine-amides. The corresponding 3-alkynyl-3-aminooxyindoles are obtained in up to 95% yield and 96% ee. The guanidine plays a role in the formation of copper acetylide and the enantiodetermining step and the basic additive is excluded.

  伊斯兰衍生的酮亚胺在碘化铜和容易获得的胍酰胺存在下进行对映选择性炔基化反应。以高达95％的收率和96％的ee获得相应的3-炔基-3-氨基氧基吲哚。胍在乙炔铜的形成和对映体确定步骤中起作用，并且不包括碱性添加剂。
• Direct enantio- and diastereoselective Mannich reactions of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine
  作者：Yuxin Liu、Jingdong Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1039/c8ob02595a

  日期：——

  A highly diastereo- and enantioselective Mannich reaction of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine has been developed. A series of 3-substituted 3-amino-oxindoles containing assembled bicyclic rings linked by a C–C bond were constructed by this protocol in excellent yields (92–99%) with high enantioselectivities (85–99% ee) and

  已经开发了由衍生自氢醌的手性硫脲催化的衍生自靛红的酮亚胺与氧代-茚满羧酸酯的高度非对映和对映选择性的曼尼希反应。通过该方案可构建一系列包含通过CC键连接的组装双环的3-取代的3-氨基-羟吲哚，并具有优异的收率（92-99％），高对映选择性（85-99％ee）和非对映选择性（向上到> 99：1博士）。