3-benzoylmethylidene-2-oxindole | 31541-36-3

• 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-benzoylmethylidene-2-oxindole
• 英文别名: 3-(2-oxo-2-phenylethylidene)indolin-2-one；3-phenacylideneoxindole；3-phenacylidene-1H-indol-2-one
• CAS: 31541-36-3
• 化学式: C₁₆H₁₁NO₂
• mdl: MFCD00652991
• 分子量: 249.269
• InChiKey: HYHFPMWIIOXTBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 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：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  3-benzoylmethylidene-2-oxindole 在 双氧水 作用下， 生成 spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one
  参考文献：
  名称：

  Ultrasound promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water

  摘要：

  An aqueous mediated novel synthesis of substituted 2'amino-4'benzoyl-2'-methyl spiro[indole 3,5'-[1,3]oxathiolane]-2(1H)-ones (2a-f) was carried out from the reaction of spiro [indole-3,2'-oxiranes] (1a-f) with thioacetamide in the presence of LiBr as catalyst. The reaction was carried out under both microwaves and sonication and results were also compared with conventional method. in general, improvement in rate and yields observed when reaction was carried out under sonication as compared to microwave irradiation and conventional method. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.08.003
• 作为产物：
  描述：

  3-羟基-3-(2-氧代-2-苯基乙基)-1,3-二氢-2H-吲哚-2-酮 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以86%的产率得到3-benzoylmethylidene-2-oxindole
  参考文献：
  名称：

  Synthesis of Spiro Heterocyclic Compounds

  摘要：

  异色酮与苯乙酮衍生物反应生成3-羟基-3-苯乙酰基氧吲哚衍生物<粗体>(II)，<粗体>(II)的脱水反应生成3-苯乙酰亚甲基-2-吲哚酮衍生物<粗体>(III)。将<粗体>(III)与水合肼、苯肼和苯硫脲缩合，分别得到新的螺环吡唑啉<粗体>(IV和V)和螺环嘧啶硫脲<粗体>(VI)。最终产物的结构经过物理和光谱手段得到确认。

  DOI：

  10.1155/2010/604549

文献信息

• Stereoselective Synthesis of Tetrahydroindolizines through the Catalytic Formation of Pyridinium Ylides from Diazo Compounds
  作者：Jonathan Day、Ben McKeever-Abbas、James Dowden

  DOI：10.1002/anie.201511047

  日期：2016.5.4

  compounds, pyridines, and electrophilic alkenes to give alkaloid‐inspired tetrahydroindolizidines in high yield with high diastereoselectivity. Hitherto, the catalytic formation of versatile pyridinium ylides from metal carbenes has been poorly developed; the broad utility demonstrated herein sets the stage for the invention of further multicomponent reactions in future.

  市售的铁（III）和铜（I）配合物催化重氮化合物，吡啶和亲电烯烃之间的多组分环加成反应，从而以高收率和高非对映选择性提供了生物碱启发的四氢吲哚并咪唑。迄今为止，由金属卡宾催化形成多用途吡啶鎓叶立德的反应还很不发达。本文证明的广泛用途为将来进一步的多组分反应的发明奠定了基础。
• 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。
• Catalytic Asymmetric <i>exo′</i> ‐Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin‐3,3′‐oxindole]s
  作者：Atsuko Awata、Takayoshi Arai

  DOI：10.1002/chem.201201249

  日期：2012.7.2

  The first catalytic asymmetric exo′‐selective [3+2] cycloaddition of methyleneindolinones with iminoesters was achieved for construction of novel diastereomers of spiro[pyrrolidin‐3,3′‐oxindole]. By using the imidazoline–aminophenol‐ligand complex [Ni(OAc)2–(L1)], the reaction proceeds in the stepwise Michael–Mannich reaction to give the exo′ adducts as stable isomers (see scheme).

  第一催化不对称 外切'与iminoesters methyleneindolinones的-选择性[3 + 2]环加成物用于建筑螺新颖非对映体[吡咯烷-3,3'-吲哚]的实现。通过使用咪唑啉-氨基苯酚-配体配合物[Ni（OAc）2-（L1）]，该反应以逐步的Michael-Mannich反应进行，得到了exo'加合物，为稳定的异构体（参见方案）。
• Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles
  作者：Ling-Ling Wu、Gao H. Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2017.02.035

  日期：2017.4

  The Rose Bengal sensitized intermolecular [2 + 2]-cycloaddition of 3-ylideneoxindoles for the synthesis of spirocyclic oxindoles was developed successfully under visible light irradiation conditions. The cycloaddition products were obtained in good yields (up to 93%) with excellent diastereoselectivity and regioselectivity by using a low loading of Rose Bengal (0.125 mol%) as a triplet sensitizer.

  在可见光照射条件下，成功开发了玫瑰孟加拉敏化的3-亚硝基氧吲哚的分子间[2 + 2]-环加成反应，用于合成螺环内的羟吲哚。通过使用少量的玫瑰红（0.125mol％）作为三重态敏化剂，以良好的非对映选择性和区域选择性以良好的产率（高达93％）获得了环加成产物。这项工作证明了玫瑰红在可见光催化中的潜在益处。
• 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。