3-(2-(4-fluorophenyl)-2-oxoethylidene)indolin-2-one | 98711-39-8

• 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
• 英文名称: 3-(2-(4-fluorophenyl)-2-oxoethylidene)indolin-2-one
• 英文别名: 2H-Indol-2-one, 3-[2-(4-fluorophenyl)-2-oxoethylidene]-1,3-dihydro-；3-[2-(4-fluorophenyl)-2-oxoethylidene]-1H-indol-2-one
• CAS: 98711-39-8
• 化学式: C₁₆H₁₀FNO₂
• 分子量: 267.259
• InChiKey: DLUFVMJZPFKJCP-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C(Solv: methanol (67-56-1))
• 沸点：
  485.4±45.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-(4-fluorophenyl)-2-oxoethylidene)indolin-2-one 在 双氧水 、 十六烷基三甲基溴化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.2h， 以96%的产率得到(3R,3'R)-3'-(4-fluorobenzoyl)spiro[1H-indole-3,2'-oxirane]-2-one
  参考文献：
  名称：

  Facile stereoslective synthesis of spiro[indole-oxiranes] by combination of phase transfer catalyst and ultrasound irradiation and their bioassay

  摘要：

  An alternative and environmentally benign pathway for diastereoslective synthesis of fluorinated spiro[indole-3,2'-oxirane]-3'-benzoyl-2(1H)-ones (2a-g) is reported. The spiro[indole-3.2'-oxiranes] derivatives were obtained in 90-97% yield exclusively via the epoxidation of 3-aroylmethylene indole-2-ones with 30% aqueous hydrogen peroxide using cetyltrimethyl ammonium bromide as a phase transfer catalyst under ultrasound irradiation. The lead compounds have been tested for their antimicrobial activity and antioxidant properties. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2010.12.010
• 作为产物：
  描述：

  4-氟苯乙酮 在 盐酸 、 溶剂黄146 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-(2-(4-fluorophenyl)-2-oxoethylidene)indolin-2-one
  参考文献：
  名称：

  Joshi, Krishna C.; Jain, Renuka; Arora, Seema, Heterocycles, 1987, vol. 26, # 7, p. 1835 - 1839

  摘要：

  DOI：

文献信息

• Unexpected isocyanide-based cascade cycloaddition reaction with methyleneindolinone
  作者：Jian Li、Shikuan Su、Mengyuan Huang、Boyi Song、Chunju Li、Xueshun Jia

  DOI：10.1039/c3cc46237d

  日期：——

  An unprecedented cascade reaction of isocyanide and methyleneindolinone has been established, which represents a novel and different reaction mode. This present transformation involves the ring-opening of methyleneindolinone and the construction of two other new rings simultaneously in an atom-economic manner.

  已经建立了前所未有的异氰酸酯与亚甲基吲哚酮的级联反应，它代表了一种新颖而又不同的反应模式。该当前的转化涉及以原子经济的方式同时打开亚甲基吲哚酮的开环和同时构建另外两个新的环。
• Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles
  作者：Ke Chen、Ting Xu、Jian Liang、Meng Zhou、Jie Zhang、Wen-Juan Hao、Jianyi Wang、Shu-Jiang Tu、Bo Jiang

  DOI：10.1039/c9cc08762a

  日期：——

  A Lewis acid-catalyzed insertion of unsymmetrical alkynes into electron-deficient alkenes was developed for the first time, and used to produce 34 hitherto unreported pentacyclic benzo[5,6]chromeno[2,3-b]indoles with generally good yields and complete stereoselectivity. A Yb(OTf)3-catalyzed reaction between o-alkynylnaphthols and 3-methyleneindolin-2-ones proceeded efficiently, and provided a simple

  首次开发了路易斯酸催化的不对称炔烃插入缺电子烯烃中的方法，该方法用于生产34例迄今未报道的五环苯并[5,6] chromeno [2,3-b]吲哚，收率通常较高，而且完全立体选择性。Yb（OTf）3催化的邻炔基萘和3-亚甲基吲哚-2-酮之间的反应有效地进行，并通过无氧化剂的CC双键断裂/重排为炔烃双官能化提供了一个简单且收敛的方案。通过进行系统的理论计​​算，得出了该多米诺过程的机械细节。
• BF₃·OEt₂ Mediated Regioselective Reaction of Electron-Rich Arenes with 3-Ylidene Oxindoles
  作者：Nitika Sharma、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.6b02395

  日期：2017.1.20

  A BF3·OEt2 mediated novel and regioselective protocol for the construction of a C–C bond between 3-ylidene oxindoles and electron-rich arenes has been successfully accomplished. The reaction was compatible with a wide variety of electron-rich arenes. A cascade reaction of 3-ylidene oxindoles with phenols and β-naphthol resulted in 2,3-difunctionalized benzofuran and lactone bearing indoline-2-one scaffolds

  已经成功完成了由BF 3 ·OEt 2介导的新颖的和区域选择性的方案，用于在3-亚甲基氧吲哚和富电子芳烃之间建立C–C键。该反应与多种富电子芳烃相容。在相同条件下，3-亚甲基羟吲哚与酚和β-萘酚的级联反应产生带有2,3-二官能化的苯并呋喃和内酯的二氢吲哚-2-酮骨架。
• A New [2+2+1] Heterocyclization for the Synthesis of 2,3,5-Trisubstituted Thiophenes under Microwave Irradiation
  作者：Bo Jiang、Shu-Jiang Tu、Hai-Wei Xu、Guan-Hua Ma

  DOI：10.1055/s-0033-1339917

  日期：——

  Abstract A new three-component strategy for the efficient synthesis of 2,3,5-trisubstituted thiophene derivatives through a [2+2+1] heterocyclization between 3-(2-aryl-2-oxoethylidene)-2-oxindoles and α-thiocyanato ketones under microwave irradiation is described. The bond-forming efficiency, accessibility, and generality of this synthesis make it highly valuable to assemble thiophene scaffolds. A new three-component

  摘要 通过3-（2-芳基-2-氧代亚乙基）-2-氧吲哚和α-硫氰酸根的[2 + 2 + 1]杂环有效合成2,3,5-三取代噻吩衍生物的新的三组分策略描述了在微波辐射下的酮。这种合成方法的成键效率，可及性和通用性使得组装噻吩支架具有很高的价值。 通过3-（2-芳基-2-氧代亚乙基）-2-氧吲哚和α-硫氰酸根的[2 + 2 + 1]杂环有效合成2,3,5-三取代噻吩衍生物的新的三组分策略描述了在微波辐射下的酮。这种合成方法的成键效率，可及性和通用性使得组装噻吩支架具有很高的价值。
• Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine E
  作者：De-Feng Li、Kun Liu、Yi-Xuan Jiang、Yan Gu、Jing-Ru Zhang、Li-Ming Zhao

  DOI：10.1021/acs.orglett.8b00045

  日期：2018.2.16

  development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available prenyl bromide using inexpensive CeCl3 as the catalyst. The new transformation tolerates a wide range of 3-acylidene-oxindoles, providing easy access to a variety

  描述了用简单的试剂快速，高效，一锅合成C3-α-戊烯基化的吲哚的方法。该方法基于使用便宜的CeCl 3作为催化剂，用市售的异戊烯基溴与锌介导的3-丙叉基-氧吲哚的α-区域选择性烯丙基化。新的转化方法可耐受各种3-丙炔基-羟吲哚，可轻松获得各种功能化的3-烯丙基化的羟吲哚。该方法的合成效用通过氟他胺家族生物碱（±）-去溴氟胺E的形式合成得到证实。