3-Allyl-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one | 206064-06-4

• 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: 3-Allyl-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one
• 英文别名: 1-[(4-methoxyphenyl)methyl]-3-prop-2-enyl-3H-indol-2-one
• CAS: 206064-06-4
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: ZOEFCUMHSVVKQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[甲氧基(二苯基)甲基]-1-[(E)-2-硝基乙烯基]吡咯烷 、 3-Allyl-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one 在 正丁基锂 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 4.0h， 以87%的产率得到(S)-3-Allyl-1-(4-methoxy-benzyl)-3-((E)-2-nitro-vinyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Enantioselective Creation of Quaternary Carbon Centers through Addition- Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles

  摘要：

  Nitroolefination of 3-substituted 2-oxindoles with nitroenamine (5) afforded the corresponding products having quaternary carbon centers with high ee in good yield. Application of this method to concise syntheses of (-)-esermethole (24) and (-)-pseudophrynaminol (28) is described.

  DOI：

  10.3987/com-97-s(n)107
• 作为产物：
  描述：

  1-(4-methoxybenzyl)indolin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 3-Allyl-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Catalytic Asymmetric Hydroxylation of Oxindoles by Molecular Oxygen Using a Phase-Transfer Catalyst

  摘要：

  The highly enantioselective catalytic hydroxylation of 3-substituted oxindoles was achieved by using a phase-transfer catalyst with molecular oxygen as an oxidant. The product then was converted to an optically active compound 8, which was a synthetic precursor of alkaloid CPC-1.

  DOI：

  10.1021/ol800260r

文献信息

• Enantioselective Synthesis of Quaternary Carbon Stereocenters: Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Pentanidiums
  作者：Lili Zong、Shubo Du、Kek Foo Chin、Chao Wang、Choon-Hong Tan

  DOI：10.1002/anie.201503844

  日期：2015.8.3

  3‐alkyloxindoles to phenyl vinyl sulfone has been demonstrated. This approach allows the construction of 3,3‐dialkyl‐substituted oxindole frameworks with high yield and excellent enantioselectivity (up to 99 %) under simple phase‐transfer conditions. A variety of oxindoles bearing all‐carbon quaternary stereogenic centers were obtained in the presence of 0.25 mol % pentanidium. Meanwhile, practicality was

  证明了戊烷催化的3-烷基氧吲哚向苯乙烯基砜的高对映选择性共轭加成反应。这种方法允许在简单的相转移条件下以高收率和出色的对映选择性（高达99％）构建3,3-二烷基取代的羟吲哚骨架。在0.25摩尔％的戊ani存在下，获得了各种带有全碳四元立体异构中心的羟吲哚。同时，通过两个3,3-二烷基取代的羟吲哚的克级不对称合成说明了实用性。生成的加合物可以通过短合成路线顺利转化为天然产物类似物。
• Pentanidium catalyzed enantioselective hydroperoxidation of 2-oxindole using molecular oxygen
  作者：Shun Zhou、Lin Zhang、Chun Li、Yuanhu Mao、Jianta Wang、Ping Zhao、Lei Tang、Yuanyong Yang

  DOI：10.1016/j.catcom.2016.04.016

  日期：2016.7

  Pentanidium catalyzed enantioselective 3-hydroperoxidation of 2-oxindoles with molecular oxygen has been established. Various 3-hydroperoxy-2-oxindoles were achieved in good ee and yield.

  已建立了戊氧鎓催化2-氧吲哚与分子氧的对映选择性3-氢过氧化反应。以良好的ee和收率获得了各种3-氢过氧-2-氧吲哚。
• Bui, Tommy; Candeias, Nuno R.; Barbas, Carlos F. III, Journal of the American Chemical Society, 2010, vol. 132, p. 5574 - 5575
  作者：Bui, Tommy、Candeias, Nuno R.、Barbas, Carlos F. III

  DOI：——

  日期：——
• Pentanidium–Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen
  作者：Yuanyong Yang、Farhana Moinodeen、Willy Chin、Ting Ma、Zhiyong Jiang、Choon-Hong Tan

  DOI：10.1021/ol302030v

  日期：2012.9.21

  Pentanidium-catalyzed alpha-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxicle oxindole via reduction with enolates generated from the oxindoles.
• Phase-Transfer Catalyzed Sulfenylation of 3-Substituted-2-oxindoles
  作者：Takashi Itoh、Kazuhiro Nagata、Daisuke Sano、Osamu Aoyama、Takuya Kanemitsu、Michiko Miyazaki、Yuki Odanaka、Ayano Machida

  DOI：10.3987/com-16-13414

  日期：——

  Optically active 3-sulfenyl-2-oxindoles were synthesized by a asymmetric substitution with a chiral phase-transfer catalyst. The reaction was suggested to proceed in a radical mechanism.