(R)-tert-butyl 3-((R)-2-nitro-1-phenylethyl)-2-oxo-3-phenylindoline-1-carboxylate | 1197418-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-tert-butyl 3-((R)-2-nitro-1-phenylethyl)-2-oxo-3-phenylindoline-1-carboxylate
• 英文别名: tert-butyl (R)-3-[(R)-2-nitro-1-phenylethyl]-2-oxo-3-phenylindoline-1-carboxylate；(3R)-tert-butyl 3-phenyl-3-[(1R)-2-nitro-1-phenylethyl]-2-oxoindoline-1-carboxylate；tert-butyl (3R)-3-[(1R)-2-nitro-1-phenylethyl]-2-oxo-3-phenylindole-1-carboxylate
• CAS: 1197418-27-1
• 化学式: C₂₇H₂₆N₂O₅
• 分子量: 458.514
• InChiKey: PNWJRLVCHZKDAR-AJTFRIOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 3-((R)-2-nitro-1-phenylethyl)-2-oxo-3-phenylindoline-1-carboxylate 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 以52%的产率得到tert-butyl (2-((3S,4S)-2-oxo-3,4-diphenylpyrrolidin-3-yl)phenyl)carbamate
  参考文献：
  名称：

  Synthesis of Lactams by Isomerization of Oxindoles Substituted at C-3 by an ω-Amino Chain

  摘要：

  Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by omega-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (3096%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams alpha-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.

  DOI：

  10.1021/jo501978j
• 作为产物：
  描述：

  β-硝基苯乙烯 、 tert-butyl 2-oxo-3-phenylindoline-1-carboxylate 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 (R)-tert-butyl 3-((R)-2-nitro-1-phenylethyl)-2-oxo-3-phenylindoline-1-carboxylate
  参考文献：
  名称：

  手性仲胺催化N-Boc保护的羟吲哚与硝基烯烃的不对称迈克尔加成反应

  摘要：

  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）。

  DOI：

  10.1002/chem.201200079

文献信息

• Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes
  作者：Wen Yang、Jingsi Wang、Da-Ming Du

  DOI：10.1016/j.tetasy.2012.06.018

  日期：2012.7

  An efficient diastereo- and enantioselective Michael addition of 3-substituted oxindoles onto nitroalkenes catalyzed by a bifunctional chiral squaramide catalyst has been developed. This organocatalytic reaction with 2 mol % of catalyst proceeded smoothly to afford 3,3-disubstituted oxindoles in high yields with good diastereoselectivities and enantioselectivities (up to 98:2 dr, 88% ee).

  已经开发了在双官能手性方酰胺催化剂催化下的3-取代的羟吲哚到硝基烯烃上的高效非对映和对映选择性迈克尔加成反应。该有机催化与2摩尔％的催化剂的反应顺利进行，以高收率提供了3,3-二取代的羟吲哚，具有良好的非对映选择性和对映选择性（最高98：2 dr，88％ee）。
• Asymmetric Michael Addition Reaction of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Alkyl- Substituted Thiourea Catalyst
  作者：Xin Li、Bo Zhang、Zhi-Guo Xi、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/adsc.200900630

  日期：2010.2.15

  A simple alkylthiourea was found to be an effective catalyst for the Michael addition reaction of 3-substituted oxindole to nitroolefins. A number of 3,3′-substituted oxindole derivatives, which have two vicinal quaternary-tertiary chiral centers were synthesized with up to 99% yield, 19:1 dr and 98% ee.

  发现简单的烷基硫脲是3-取代的羟吲哚与硝基烯烃的迈克尔加成反应的有效催化剂。合成了多个具有两个相邻的季-三级手性中心的3,3'-取代的吲哚衍生物，收率高达99％，dr为19：1和ee为98％。
• 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）。
• Chiral Bifunctional Thiosquaramides as Organocatalysts in the Synthesis of Enantioenriched 3,3-Disubstituted Oxindoles
  作者：Patricia Rodríguez-Ferrer、Daniel Naharro、Alicia Maestro、José M. Andrés、Rafael Pedrosa

  DOI：10.1002/ejoc.201901327

  日期：2019.10.17

  Four novel chiral bifunctional thiosquaramides have been prepared from cyclopentyl dithiosquarates and diamines derived from natural l‐valine and l‐tert‐leucine. The novel thiosquaramides have been tested as organocatalyst in the nitro‐Michael addition of 3‐substituted oxindoles to different β‐aryl‐substituted nitroalkenes. The reaction occurred easily in high yields and excellent stereoselectivities

  从环戊基二硫代方酸和天然l-缬氨酸和l-叔亮氨酸衍生的二胺制备了四种新型手性双官能硫代方酸酰胺。在将3-取代的羟吲哚的硝基-迈克尔加成到不同的β-芳基取代的硝基烯烃中作为有机催化剂时，已经测试了新型的硫代四氢呋喃酰胺。该反应容易以高收率和优异的立体选择性发生。
• A Base-Free Neutral Phase-Transfer Reaction System
  作者：Seiji Shirakawa、Lijia Wang、Rongjun He、Satoru Arimitsu、Keiji Maruoka

  DOI：10.1002/asia.201402194

  日期：2014.6

  phase‐transfer reaction system can be applied to highly enantioselective conjugate addition and aldol reactions under the influence of chiral bifunctional ammonium bromides as key catalysts. The structure of the chiral ammonium enolate intermediate is discussed based on the single‐crystal X‐ray structures of relevant ammonium salts and the importance of bifunctional design of catalyst is clearly explained in the

  尽管一般认为使用季铵盐催化的相转移反应需要碱添加剂，但我们发现，即使没有任何碱添加剂，在存在亲脂性季铵溴化物的情况下，在水中将3-取代的羟吲哚共轭添加到硝基烯烃中也能顺利进行。 –有机两相条件。研究了这种新型的无碱中性相转移反应体系的机理，并提出了假定的催化循环以及水和相转移催化剂的亲脂性的有趣影响。无碱中性相转移反应体系可在手性双官能溴化铵作为关键催化剂的情况下用于高对映选择性共轭加成和醛醇缩合反应。