1-烯丙基-6-溴二氢吲哚-2,3-二酮 | 1020932-60-8

• 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
• 中文名称: 1-烯丙基-6-溴二氢吲哚-2,3-二酮
• 英文名称: 1-allyl-6-bromoindoline-2,3-dione
• 英文别名: N-allyl-6-bromoisatin；6-Bromo-1-prop-2-enylindole-2,3-dione
• CAS: 1020932-60-8
• 化学式: C₁₁H₈BrNO₂
• 分子量: 266.094
• InChiKey: PCSRYWQBODTWCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-烯丙基-6-溴二氢吲哚-2,3-二酮 在 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium tetrahydroborate 、 臭氧 、 N,N-二异丙基乙胺 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-苯基膦-1-萘酰基) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 54.5h， 生成 6-bromo-1-(2-hydroxyethyl)-5'-(3-hydroxypropyl)-5'-methyl-5',6'-dihydrospiro[indoline-3,4'-pyran]-2,2'(3'H)-dione
  参考文献：
  名称：

  Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

  摘要：

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.

  DOI：

  10.1021/ja2020873
• 作为产物：
  描述：

  6-溴靛红 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.17h， 生成 1-烯丙基-6-溴二氢吲哚-2,3-二酮
  参考文献：
  名称：

  Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

  摘要：

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.

  DOI：

  10.1021/ja2020873

文献信息

• Chiral Naphthyl-C2-Indole as Scaffold for Phosphine Organocatalysis: Application in Asymmetric Formal [4 + 2] Cycloaddition Reactions
  作者：Tingting He、Lei Peng、Shan Li、Fangli Hu、Chuandong Xie、Shengli Huang、Shiqi Jia、Wenling Qin、Hailong Yan

  DOI：10.1021/acs.orglett.0c02519

  日期：2020.9.4

  naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine organocatalysis for the first time, and excellent stereocontrol was achieved in two types of formal [4 + 2] cycloaddition reactions. With the optimal catalyst, a series of chiral spirooxindole and hydrodibenzofuran

  报道了一种新设计的手性萘-C2-吲哚双功能膦有机催化剂在立体选择性形式[4 + 2]环加成反应中的应用。首次将手性萘基C2-吲哚骨架引入双功能膦有机催化中，并在两种类型的正式[4 + 2]环加成反应中实现了出色的立体控制。使用最佳的催化剂，可以以中等至良好的收率和优异的立体选择性（高达> 99％ee，> 20：1 dr）生产一系列手性螺并吲哚和氢二苯并呋喃结构。
• A Deoxygenative [4+1] Annulation Involving<i>N</i>-Acyldiazenes for an Efficient Synthesis of 2,2,5-Trisubstituted 1,3,4-Oxadiazole Derivatives
  作者：Rong Zhou、Ling Han、Honghui Zhang、Rongfang Liu、Ruifeng Li

  DOI：10.1002/adsc.201700935

  日期：2017.11.23

  + 1] annulation of N-acyldiazenes with α-dicarbonyl compounds such as isatins, α-keto esters, and α-diketones is reported. The annulation reactions proceed smoothly under mild conditions to deliver a broad range of 2,2,5-trisubstituted 1,3,4-oxadiazole derivatives in moderate to excellent yields from readily available starting materials. It represents the first realization of the [4+1] annulation mode

  前所未有的，高效的三（二甲基氨基）膦[P（NMe 2）3 ]介导的N-酰基二氮烯与α-二羰基化合物（如靛红，α-酮酸酯和α-二酮）的脱氧[4 +1]环化反应报告。在温和的条件下，环化反应可顺利进行，从容易获得的起始原料中以中等至极好的收率提供各种2,2,5-三取代的1,3,4-恶二唑衍生物。它代表了[4 + 1]环化模式的第一个实现，该模式涉及N-酰基二氮烯以构建五元杂环。
• Unusual Formal [1+4] Annulation through Tandem P(NMe₂ )₃ -Mediated Cyclopropanation/Base-Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones
  作者：Rong Zhou、Kai Zhang、Ling Han、Yusong Chen、Ruifeng Li、Zhengjie He

  DOI：10.1002/chem.201505047

  日期：2016.4.18

  An unusual formal [1+4] annulation of α‐dicarbonyl compounds with 1,1‐dicyano‐1,3‐dienes has been realized, leading to facile syntheses of cyclopentenimines and cyclopentenones in a unique manner. Mechanistic investigation implies that this reaction takes place through a P(NMe2)3‐mediated cyclopropanation followed by a base‐catalyzed cyclopropane rearrangement. It therefore represents an unprecedented

  已经实现了α-二羰基化合物与1,1-二氰基-1,3-二烯的不寻常形式化[1 + 4]环合，从而以独特的方式容易地合成了环戊烯亚胺和环戊烯酮。机理研究表明，该反应是通过P（NMe 2）3介导的环丙烷化反应进行的，然后再进行碱催化的环丙烷重排反应。因此，它代表了空前的[1 + 4]环空模式，涉及库赫金-拉米雷斯加合物。
• 一种2,2,5-三取代1,3,4噁二唑衍生物及其合 成方法
  申请人：太原理工大学

  公开号：CN107445914B

  公开（公告）日：2019-12-17

  本发明公开了一种2,2,5‑三取代1,3,4‑噁二唑衍生物及其合成方法，属于有机合成技术领域。通过N‑酰基双氮杂烯烃与α‑二羰基化合物在三配位磷试剂的促进下反应得到2,2,5‑三取代1,3,4‑噁二唑衍生物。本发明的反应条件温和、底物适用范围宽、官能团容忍性好；提供了一种高效合成结构新颖的2,2,5‑三取代1,3,4‑噁二唑衍生物的合成技术；本发明为开发新的噁二唑类药物分子提供了候选化合物。
• An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones
  作者：Julien Dugal-Tessier、Elizabeth A. O'Bryan、Thomas B. H. Schroeder、Daniel T. Cohen、Karl A. Scheidt

  DOI：10.1002/anie.201201643

  日期：2012.5.14

  cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β‐unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β‐aryl enals catalyzed by an N‐heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC‐catalyzed annulation has been used for the total synthesis of maremycin B.

  α,β-不饱和醛与靛红的对映选择性正式[3+2]加成协同催化方法已被开发。由 N-杂环卡宾 (NHC) 催化的 β-芳基烯醛的均烯化环需要添加氯化锂以获得高水平的对映选择性。这种 NHC 催化的环化已用于马雷霉素 B 的全合成。