3-phenyl-5-fluoro-oxindole | 1235862-80-2

• 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-fluoro-oxindole
• 英文别名: 5-fluoro-3-phenylindolin-2-one；5-Fluoro-3-phenyl-1,3-dihydroindol-2-one；5-fluoro-3-phenyl-1,3-dihydroindol-2-one
• CAS: 1235862-80-2
• 化学式: C₁₄H₁₀FNO
• 分子量: 227.238
• InChiKey: TVTKVFGQICBYPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-fluoro-oxindole 在 air 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以62%的产率得到5-fluoro-3-hydroxy-3-phenylindolin-2-one
  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
• 作为产物：
  描述：

  5-氟靛红 在 盐酸 、 sodium hydride 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 3-phenyl-5-fluoro-oxindole
  参考文献：
  名称：

  对映体富集的C简便合成γ经由不对称亲核加成/质子化级联-Tetrasubstitutedα氨基酸衍生物

  摘要：

  已经描述了3-取代的羟吲哚和2-邻苯二甲酰亚胺基丙烯酸乙酯的不对称亲核加成/质子化反应。这种策略可以给予至C直接访问γ -tetrasubstitutedα氨基酸衍生物轴承1,3-不相邻的立体中心具有高达98％的收率，94：6 DR，和> 99％ee的。提出了在过渡态下的双重活化，并且可以简单地通过将辛可尼丁衍生的催化剂改变为辛可宁类似物来获得相反的对映异构体。

  DOI：

  10.1021/ol200550y

文献信息

• Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins
  作者：Miao Ding、Feng Zhou、Zi-Qing Qian、Jian Zhou

  DOI：10.1039/c004037a

  日期：——

  Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.

  奎尼丁业已发现以高产率和中等至良好的非对映选择性催化将未保护的3-取代的羟吲哚的迈克尔加成到硝基烯烃上。双功能奎尼丁 衍生的 硫脲催化剂10可以催化该反应以提供最多85％ee的主要非对映异构体。
• 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。
• Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
  作者：Jin-Sheng Yu、Feng Zhou、Yun-Lin Liu、Jian Zhou

  DOI：10.3762/bjoc.8.157

  日期：——

  We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD)₂PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.

  我们报道了第一个无保护的3-丙基氧吲哚1与1,4-萘醌进行有机催化Michael加成的例子。发现喹啉衍生物(DHQD)₂PYR能够催化该反应，使得产物的对映选择性高达83%，收率从中等到极好。这种方法可以用于合成对映富集的3,3-二芳基氧吲哚，而且这种催化合成方法是前所未有的。
• 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。
• Chiral Calcium Phosphate-Catalyzed Enantioselective Amination of 3-Aryl-2-oxindoles with Dibenzyl Azodicarboxylate
  作者：Zhenwei Wu、Suvratha Krishnamurthy、K. S. Satyanarayana Tummalapalli、Jon C. Antilla

  DOI：10.1021/acs.joc.2c00432

  日期：2022.6.17

  A chiral calcium phosphate-catalyzed enantioselective amination of 2-oxindoles with dibenzyl azodicarboxylate has been developed, affording the products in consistently high yields and excellent enantioselectivity. This synthetic method features low catalyst loading and a high catalytic efficiency. Moreover, the practical value of this process is well demonstrated by a scale-up experiment and a trial

  已经开发了一种手性磷酸钙催化的 2-羟吲哚与偶氮二甲酸二苄酯的对映选择性胺化，以始终如一的高产率和优异的对映选择性提供产物。该合成方法具有催化剂负载量低、催化效率高的特点。此外，该工艺的实用价值通过放大实验和催化剂回收再利用的试验得到了很好的证明。