ethyl (E)-2-(5-bromo-2-oxoindolin-3-ylidene)acetate | 887130-97-4

• 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: ethyl (E)-2-(5-bromo-2-oxoindolin-3-ylidene)acetate
• 英文别名: (E)-ethyl 2-(5-bromo-2-oxoindolin-3-ylidene)acetate；ethyl (2E)-2-(5-bromo-2-oxo-indolin-3-ylidene)acetate；ethyl (2E)-2-(5-bromo-2-oxo-1H-indol-3-ylidene)acetate
• CAS: 887130-97-4
• 化学式: C₁₂H₁₀BrNO₃
• 分子量: 296.12
• InChiKey: AJEDMQSDWJQCSG-RMKNXTFCSA-N

物化性质

• 沸点：
  467.1±45.0 °C(Predicted)
• 密度：
  1.636±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-(5-bromo-2-oxoindolin-3-ylidene)acetate 在 劳森试剂 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part I

  摘要：

  A novel oxindole was discovered as an HIV non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Systematic structural modifications were carried out to establish its SAR. These modifications led to the identification of oxindoles with low nanomolar potency for inhibiting HIV replication. These novel and potent oxindoles could serve as advanced leads for further optimizations. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.073
• 作为产物：
  描述：

  5-溴靛红 在 吡啶 、 三乙烯二胺 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 1.25h， 生成 ethyl (E)-2-(5-bromo-2-oxoindolin-3-ylidene)acetate
  参考文献：
  名称：

  威蒂希产品的Morita–Baylis–Hillman途径：硝基亚烷基氧杂吲哚的一锅法转化为亚氧杂环丁二烯-羧酸盐

  摘要：

  在Morita–Baylis–Hillman（MBH）条件（DABCO / CH 3 CN）下，硝基亚烷基新吲哚与选定的活化羰基化合物的反应导致了Wittig型产物的意外形成。尽管前两个步骤涉及MBH途径（迈克尔加成反应和羟醛反应），但此一锅法过程中的后续步骤可能是分子内取代和消除。

  DOI：

  10.1002/ejoc.202000852

文献信息

• When Ethyl Isocyanoacetate Meets Isatins: A 1,3-Dipolar/Inverse 1,3-Dipolar/Olefination Reaction for Access to 3-Ylideneoxindoles
  作者：Wen-Kui Yuan、Tao Cui、Wei Liu、Li-Rong Wen、Ming Li

  DOI：10.1021/acs.orglett.8b00217

  日期：2018.3.16

  A new CuI/1,10-phen-catalyzed reaction for the synthesis of 3-ylideneoxindoles from readily available isatins and ethyl isocyanoacetate, in which ethyl isocyanoacetate acts as a latent two-carbon donor like the Wittig reagent, is reported. A tandem procedure including 1,3-dipolar cycloaddition/inverse 1,3-dipolar ring opening/olefination allows the preparation of 3-ylideneoxindoles with broad functional

  据报道，一种新的CuI / 1,10-phen催化的反应可从易得的靛红和异氰基乙酸乙酯合成3-亚苄基吲哚，其中异氰基乙酸乙酯像Wittig试剂一样是潜在的二碳供体。串联程序包括1,3-偶极环加成反应/ 1,3-偶极反环开环反应/烯化反应，可以制备具有宽泛的官能团耐受性的3-亚硝基氧吲哚。
• An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann–Ohira reagent with methyleneindolinones
  作者：Anil M. Shelke、Gurunath Suryavanshi

  DOI：10.1039/c5ob01020a

  日期：——

  regioselective synthesis of racemic 3,3′-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann–Ohira reagent (BOR) & methyleneindolinones has been developed. The synthesis affords the highly functionalized pyrazole scaffolds in good yields with excellent regioselectivity under mild reaction conditions within

  通过一锅，从Bestmann-Ohira试剂（BOR）和亚甲基吲哚满酮原位生成的1-重氮甲基膦酸二烷基酯的原位生成的阴离子的1,3-偶极环加成反应，可以高度区域选择性地合成外消旋3,3'-螺代-膦酰基吡唑-恶吲哚发达。在温和的反应条件下，在短的反应时间内，该合成以良好的产率提供了高官能度的吡唑支架，具有出色的区域选择性。
• Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions
  作者：Bo‐Liang Zhao、Da‐Ming Du

  DOI：10.1002/adsc.201900218

  日期：2019.7.11

  three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction

  开发了一种双官能方胺催化的一锅式三锅Michael / Mannich-Michael /环化顺序级联反应，用于构建双螺新恶唑-螺新恶多，并具有良好的立体选择性（高达> 20：1 dr，99％ee）。一系列原始的肉桂酰基-3-亚硝基氧吲哚已首次应用于此顺序级联策略。这一新策略为具有7个立体中心的双螺毒素-螺毒素的对映选择性构建提供了一个过程，其中三个是四价螺立体中心。
• Steric-Hindrance-Induced Diastereoselective Radical Nitration of 3-Alkylidene-2-oxindoles Followed by Tosylhydrazine-Mediated Sulfonation
  作者：Sayan Pramanik、Pinaki Saha、Prasanta Ghosh、Chhanda Mukhopadhyay

  DOI：10.1021/acs.joc.2c01523

  日期：2023.3.17

  Metal-free radical nitration of the β C–H bond of 3-alkylidene-2-oxindoles with tert-butyl nitrite (TBN) has been explored. Interestingly, (E)-3-(2-(aryl)-2-oxoethylidene)oxindole and (E)-3-ylidene oxindole give different diastereomers on nitration. The mechanistic investigation revealed that the diastereoselectivity was controlled by the size of the functional group. Another transformation of 3-(nitroalkylidene)

  已经探索了 3-alkylidene-2-oxindoles 的 β C-H 键与亚硝酸叔丁酯 (TBN)的金属自由基硝化反应。有趣的是，( E )-3-(2-(aryl)-2-oxoethylidene)oxindole 和 ( E )-3-ylidene oxindole 在硝化时给出不同的非对映异构体。机理研究表明，非对映选择性受官能团大小的控制。通过金属和无氧化剂的甲苯磺酰肼介导的磺化作用，将 3-(硝基亚烷基) 羟吲哚转化为 3-(甲苯磺酰亚烷基) 羟吲哚。这两种方法都具有起始材料容易获得和操作简单的优点。
• Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
  作者：Chada Narsimha Reddy、V. Lakshma Nayak、Geeta Sai Mani、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Ram Awatar Maurya、Ahmed Kamal

  DOI：10.1016/j.bmcl.2015.08.056

  日期：2015.10

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.