1-benzyl-5-methyl-3-phenylindolin-2-one | 1394951-53-1

• 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: 1-benzyl-5-methyl-3-phenylindolin-2-one
• 英文别名: 1-benzyl-5-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one；1-benzyl-5-methyl-3-phenyl-3H-indol-2-one
• CAS: 1394951-53-1
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: DAGLYELLUOXLTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-methyl-3-phenylindolin-2-one 在 吡啶 、 碘苯二乙酸 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到3-azido-1-benzyl-5-methyl-3-phenylindolin-2-one
  参考文献：
  名称：

  Metal-Free C(sp³)–H Azidation in a Radical Strategy for the Synthesis of 3-Azido-2-oxindoles at Room Temperature

  摘要：

  A novel and environmentally attractive C-(sp(3))-H azidation of 2-oxindoles involving the formation of a C-N bond was developed. This methodology achieved for the first time 3-azido-2-oxindole construction under metal-free conditions at room temperature via a radical strategy. PhI(OAc)(2) was used as the oxidant and Et3N was used as the additive in this transformation. Furthermore, the mechanistic study indicated that this azidation involved a radical process.

  DOI：

  10.1021/acs.joc.8b01678
• 作为产物：
  描述：

  在 水 作用下， 以 二氯甲烷 为溶剂， 以109 mg的产率得到1-benzyl-5-methyl-3-phenylindolin-2-one
  参考文献：
  名称：

  BF3·OEt2催化重氮酰胺与芳基醛的脱羰芳基化/C-H官能化：取代3-芳基吲哚的合成

  摘要：

  开发了一种无金属BF 3 ·OEt 2催化重氮酰胺与易于获得的芳基醛在露天气氛下直接脱羰基芳基化反应，通过1,2-芳基迁移以高选择性得到3-芳基吲哚。该反应为重氮酰胺在相对温和的条件下进行 3-芳基化提供了一条有效的途径，显示出对给电子基团和吸电子基团都具有高水平的官能团耐受性和广泛的底物范围。3-芳环吲哚也通过未受保护的水杨醛衍生物的取代基控制的化学和位点选择性 C-H 键官能化获得。

  DOI：

  10.1039/d2ob00003b

文献信息

• Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement–Palladium-Catalyzed Cross-Coupling Sequence
  作者：Masahiro Terada、Azusa Kondoh、Akira Takei

  DOI：10.1055/s-0035-1561859

  日期：——

  A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin

  开发了一种从靛红衍生物有效合成 3-芳基吲哚的新方法。该方法涉及在布朗斯台德碱催化下通过[1,2]-磷酸-布鲁克重排形成在C-3位具有磷酸酯部分的羟吲哚，然后是钯催化的与芳基硼试剂的交叉偶联。还描述了从靛红衍生物中一锅法合成 3-芳基羟吲哚。
• 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。
• Highly Enantioselective Organocatalytic Sulfenylation of 3-Aryloxindoles
  作者：Zhiqiang Han、Wenchao Chen、Sheng Dong、Caiyun Yang、Hongjun Liu、Yuanhuang Pan、Lin Yan、Zhiyong Jiang

  DOI：10.1021/ol3021176

  日期：2012.9.7

  An organocatalytic asymmetric sulfenylation of 3-aryloxindoles with N-(sulfanyl)succinimides has been developed by using commercially available (DHQD)2PHAL as catalyst. Various chiral 3-benzylthio-, alkylthio-, and arylthio-substituted oxindoles, containing 3,3-disubstituted quarternary carbon stereocenters, could be obtained in high enantioselectivities (85–97% ee). Furthermore, the opposite enantiomers

  通过使用可商购的（DHQD）2 PHAL作为催化剂，开发了具有N-（亚硫烷基）琥珀酰亚胺的3-芳基羟吲哚的有机催化不对称亚硫基化反应。可以高对映选择性（85-97％ee）获得各种手性的3-苄硫基，烷硫基和芳硫基取代的羟吲哚，它们含有3,3-二取代的季碳立体中心。此外，通过用（DHQ）2 PHAL代替催化剂，可以轻松获得亚磺酰化产物的相反对映异构体，具有同等的优异对映选择性（86-95％ee）。
• Bicyclic guanidinium-catalyzed enantioselective phase-transfer alkylation: direct access to pyrroloindolines and furoindolines
  作者：Wenchao Chen、Wenguo Yang、Lin Yan、Choon-Hong Tan、Zhiyong Jiang

  DOI：10.1039/c3cc46111d

  日期：——

  Highly enantioselective phase-transfer alkylation of 3-substituted-2-oxindoles with activated bromomethanes is disclosed with a broad substrate scope by using bicyclic guanidinium as a catalyst and a Lewis acid as the co-catalyst. The alkylation adducts are versatile intermediates to accomplish the syntheses of pyrroloindolines and furoindolines.

  本发明以双环胍为催化剂，以路易斯酸为助催化剂，实现了 3-取代-2-氧吲哚与活化溴甲烷的高对映选择性相转移烷基化反应，具有广泛的底物范围。烷基化加合物是完成吡咯吲哚和呋喃吲哚合成的多功能中间体。