3-phenyl-5,7-dimethyl-oxindole | 1351707-80-6

• 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-phenyl-5,7-dimethyl-oxindole
• 英文别名: 5,7-Dimethyl-3-phenyl-1,3-dihydroindol-2-one；5,7-dimethyl-3-phenyl-1,3-dihydroindol-2-one
• CAS: 1351707-80-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: FFERAXGSGUHQHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-5,7-dimethyl-oxindole 在 盐酸 、 C₃₀H₃₀F₆N₄OS 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 120.5h， 生成 (3S)-3-amino-5,7-dimethyl-3-phenyl-1H-indol-2-one
  参考文献：
  名称：

  偶氮二叔丁基羧酸酯对未保护的3-芳基和3-脂族取代的吲哚的有机催化不对称α-氨基化

  摘要：

  发现双功能奎宁衍生的硫脲催化剂14催化了未保护的3-芳基和脂族取代的羟吲哚与偶氮二叔丁基二羧酸酯（DBAD）的直接胺化反应，从而在羟吲哚的C-3位置构建了一个四取代的立体碳中心。优良至优异的产率和对映选择性。

  DOI：

  10.1002/adsc.201100379
• 作为产物：
  描述：

  5,7-二甲基氧化吲哚 、 氯苯 在 C₃₁H₄₃Cl₂N₄Pd 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以44%的产率得到3-phenyl-5,7-dimethyl-oxindole
  参考文献：
  名称：

  N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Oxindoles with Aryl Chlorides and Aerobic Oxidation of the Products in a One-Pot Procedure

  摘要：

  NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the alpha-arylation of unprotected oxindoles with aryl chlorides to give products 4 in 44-98% yields under a N-2 atmosphere. Furthermore, if the reactions were first performed under conditions identical to those for the alpha-arylation reaction for 12 hand then exposed to air for another 3 h, 3-aryl-3-hydroxy-2-oxindoles 5 can be obtained in 49-84% yields In a one-pot procedure.

  DOI：

  10.1021/ol400186b

文献信息

• A highly efficient thiourea catalyzed dehydrative nucleophilic substitution reaction of 3-substituted oxindoles with xanthydrols
  作者：Long Chen、Feng Zhu、Cui-Hong Wang、Jian Zhou

  DOI：10.1039/c3ra44520h

  日期：——

  We report a highly efficient thiourea catalyzed dehydrative nucleophilic substitution reaction. The Schreiner's thiourea catalyst A1 catalyzed the alkylation of 3-substituted oxindoles with xanthydrols well, to furnish quaternary oxindoles in high yield. The ESI-MS analysis confirms the interaction of 3-substituted oxindole 1 with the thiourea, which might facilitate the oxindole–hydroxindole tautomerization

  我们报告了高效硫脲催化脱水亲核取代反应。Schreiner's硫脲催化剂A 1能够很好地催化三取代羟吲哚与黄嘌呤醇的烷基化反应，从而以高收率提供季羟吲哚。ESI-MS分析证实了3-取代的oxindole 1与硫脲的相互作用，这可能有助于oxindole-hydroxindole的互变异构体进行烷基化。
• Highly Stereoselective Conjugate Addition and α-Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
  作者：Zhen Wang、Zuliang Zhang、Qian Yao、Xiaohua Liu、Yunfei Cai、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.201300816

  日期：2013.6.24

  The highly Z‐selective asymmetric conjugate addition of 3‐substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N′‐dioxides under mild conditions. The thermodynamically unstable Z‐olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic

  通过在温和条件下使用手性N，N'-二氧化物的scan络合物，已开发出3-取代的羟吲哚向炔基羰基化合物的高度Z选择性不对称共轭加成反应。热力学上不稳定的Z-烯烃衍生物以优异的收率和高的对映体和几何控制得到。还发现该催化剂在3-取代的羟吲哚的不对称炔取代反应中有效，具有出色的对映选择性。
• 10.1002/asia.202400297
  作者：Zhang, Xinxin X.、Wang, Pengkai K.、Zhang, Songlin L.

  DOI：10.1002/asia.202400297

  日期：——

  A protocol has been developed for the synthesis of α-aryl-oxindoles from isatin and Grignard reagents in the presence of diphenyl phosphite for the first time. This reaction was conveniently carried out under mild conditions in a one-pot fashion with moderate to excellent yields.

  首次开发了在亚磷酸二苯酯存在下由靛红和格氏试剂合成 α-芳基-羟吲哚的方案。该反应在温和条件下以一锅方式方便地进行，具有中等至优异的产率。
• <i>N</i>-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Oxindoles with Aryl Chlorides and Aerobic Oxidation of the Products in a One-Pot Procedure
  作者：Zheng-Kang Xiao、Hui-Ying Yin、Li-Xiong Shao

  DOI：10.1021/ol400186b

  日期：2013.3.15

  NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the alpha-arylation of unprotected oxindoles with aryl chlorides to give products 4 in 44-98% yields under a N-2 atmosphere. Furthermore, if the reactions were first performed under conditions identical to those for the alpha-arylation reaction for 12 hand then exposed to air for another 3 h, 3-aryl-3-hydroxy-2-oxindoles 5 can be obtained in 49-84% yields In a one-pot procedure.
• Organocatalytic Asymmetric α-Amination of Unprotected 3-Aryl and 3-Aliphatic Substituted Oxindoles using Di-tert-butyl Azodicarboxylate
  作者：Feng Zhou、Miao Ding、Yun-Lin Liu、Cui-Hong Wang、Cong-Bin Ji、Yi-Yu Zhang、Jian Zhou

  DOI：10.1002/adsc.201100379

  日期：2011.11

  The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.

  发现双功能奎宁衍生的硫脲催化剂14催化了未保护的3-芳基和脂族取代的羟吲哚与偶氮二叔丁基二羧酸酯（DBAD）的直接胺化反应，从而在羟吲哚的C-3位置构建了一个四取代的立体碳中心。优良至优异的产率和对映选择性。