2-(1-benzyl-6-chloro-2-oxoindolin-3-ylidene)malononitrile | 1613309-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(1-benzyl-6-chloro-2-oxoindolin-3-ylidene)malononitrile
• CAS: 1613309-20-8
• 化学式: C₁₈H₁₀ClN₃O
• 分子量: 319.75
• InChiKey: CFUBUGFWYQEDOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-indolin-2-one 、 2-(1-benzyl-6-chloro-2-oxoindolin-3-ylidene)malononitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以32%的产率得到5'-amino-1''-benzyl-6''-chloro-1-methyl-2,2''-dioxodispiro[indoline-3,2'-furan-3',3''-indoline]-4'-carbonitrile
  参考文献：
  名称：

  DBU催化3-羟基羟吲哚与异亚丙基丙二腈的Michael-Pinner-异构化级联反应：进入含有完全取代的二氢呋喃基序的高度官能化的bispirooxindoles †

  摘要：

  开发了第一个DBU催化的3-氢氧吲哚与异亚丙基丙二腈的Michael / Pinner /异构化级联反应，并以高达92％的收率获得了相应的含有完全取代的二氢呋喃基序的高度官能化的bispirooxindoles。该方案还提供了一种合成α-氰基-γ-丁内酯双螺并恶唑的有效方法。另外，进行了一锅三组分级联反应。同样，获得了级联反应的不对称形式。

  DOI：

  10.1039/c6ob02254e

文献信息

• Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles
  作者：Fang-Le Hu、Yin Wei、Min Shi

  DOI：10.1002/adsc.201301070

  日期：2014.3.10

  enantioselective formal [4+2] tandem cyclizations between isatylidenemalononitriles and activated dienes catalyzed by bifunctional chiral phosphine catalysts have been developed, yielding multistereogenic spirocyclic oxindoles in high yields and excellent optical purity. This reaction is accomplished via a tandem Rauhut–Currier/Michael/Rauhut–Currier reaction sequence.

  已开发出双功能手性膦催化剂催化的异亚乙基丙二腈和活化的二烯之间的第一个高度对映选择性的正式[4 + 2]串联环化反应，可高收率和出色的光学纯度产生多立体异构螺环式吲哚。该反应是通过串联的Rauhut-Currier / Michael / Rauhut-Currier反应序列完成的。
• Asymmetric synthesis of spirooxindole–pyranoindole products <i>via</i> Friedel–Crafts alkylation/cyclization of the indole carbocyclic ring
  作者：Yuan Gao、Xiaonan Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1039/d0nj00074d

  日期：——

  An efficient enantioselective Friedel–Crafts alkylation/cyclization tandem reaction of the indole carbocyclic ring with isatylidene malononitriles has been performed successfully by using a new bifunctional tertiary amine-urea catalyst. A series of chiral spirooxindole–pyranoindole products were obtained in excellent yields (up to 98% yield) with moderate to good enantioselectivities (up to 85% ee)

  通过使用新型双功能叔胺-脲催化剂，已成功进行了吲哚碳环与异亚丙基丙二腈的高效对映选择性Friedel-Crafts烷基化/环化串联反应。以优异的收率（最高98％的收率）和中等至良好的对映选择性（最高85％ee）获得了一系列手性螺氧基吲哚-吡喃并吲哚产品。
• Synthesis of optically active 2-amino-1′-benzyl-2′,5-dioxo-5<i>H</i>-spiro[indeno[1,2-<i>b</i>]pyran-4,3′-indoline]-3-carbonitriles catalyzed by a bifunctional squaramide derived from quinine
  作者：Yuanyuan Wang、Zhonglin Wei、Jungang Cao、Dapeng Liang、Yingjie Lin、Haifeng Duan

  DOI：10.1039/d0nj06092e

  日期：——

  The first organocatalytic asymmetric reaction of propylene malononitrile with oxoindole and 1,3-indandione for the synthesis of chiral indeno-spiro compounds has been developed. Under bifunctional squaramide catalysis, a wide range of optically active 5H-spiro[indeno[1,2-b]pyran-4,3′-indoline] derivatives were obtained in excellent yields (up to 95%) with moderate to good enantioselectivities (up to 82%)

  已经开发了丙烯丙二腈与氧代吲哚和1，3-茚满二酮的第一有机催化不对称反应，用于合成手性茚并-螺环化合物。在双功能方酰胺催化下，以优异的收率（高达95％）和中等至良好的对映选择性获得了多种旋光的5 H-螺[茚并[1,2 - b ]吡喃-4,3'-二氢吲哚]衍生物（高达82％）。通过大多数产品的简单重结晶过程即可达到90-99％的对映选择性。这些茚并螺化合物是药物发现和生物化学的有希望的候选者。
• Asymmetric Synthesis of Multicyclic Spirooxindole Derivatives Bearing Stereogenic Quaternary Carbon Atoms
  作者：Xiaoyi Li、Zihao Li、Rong Zhang、Zhen Zhou、Yonghui Zhang、Yi Xia、Weijun Yao、Zhen Wang

  DOI：10.1021/acs.orglett.3c00705

  日期：2023.4.21

  organocatalyzed stereoselective domino reaction as a facile approach to multicyclic spirooxindole derivatives bearing two stereogenic quaternary carbon atoms is reported. The alkyl-substituted chiral thiourea catalyst was efficient for the reaction to tolerate a wide range of substrates, furnishing a new class of spirooxindole derivatives bearing an O,O-acetal-fused tricyclic skeleton or tetrahydroxanthone moiety

  报道了一种有机催化的立体选择性多米诺骨牌反应，作为一种简便的方法来制备带有两个立体异构季碳原子的多环螺吲哚衍生物。烷基取代的手性硫脲催化剂对于耐受各种底物的反应是有效的，以中等到良好的收率和良好到优异的性能提供一类带有 O，O-缩醛稠合三环骨架或四氢氧杂蒽酮部分的新型螺氧吲哚衍生物选择性。这种方法产生的产品具有很好的抗癌活性。
• Ultrafast and Diastereoselective Synthesis of 3-Spirocyclopropyl-2-oxindoles Bearing Three Continuous All-Carbon Quaternary Centers
  作者：Yong Zhu、Tao Lu、Aixin Geng、Hao Cui、Liyuan Zhang

  DOI：10.3987/com-19-14078

  日期：——

  Synthesis of 3-spirocyclopropyl-2-oxindoles bearing three continuous all-carbon quaternary centers by the domino Michael-alkylation reaction between 3-chlorooxindole and isatylidenemalononitrile is described. Remarkably, the reaction proceeded in exceptionally high efficiency (up to 99% yield within 2 min) and excellent diastereoselectivity (>25:1 dr for all the examples).