2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile | 135643-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile
• 英文别名: 2-[3-oxoisobenzofuran-1(3H)-ylidene]malononitrile；2-(3-oxo-2-benzofuran-1-ylidene)propanedinitrile
• CAS: 135643-48-0
• 化学式: C₁₁H₄N₂O₂
• 分子量: 196.165
• InChiKey: FHFLYMLDQHIJEO-UHFFFAOYSA-N

物化性质

• 沸点：
  341.3±42.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile 、 二聚氰胺 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到N-(6'-amino-5'-cyano-3-oxo-1'H,3H-spiro(isobenzofuran-1,4'-pyrimidine)-2'-yl)cyanamide
  参考文献：
  名称：

  由 2-(3-oxoisobenzofuran-1(3H)-ylidene)丙二腈和双亲核试剂合成螺杂环系统

  摘要：

  由邻苯二甲酸酐和丙二腈生成的 2-(3-oxoisobenzofuran-1(3H)-ylidene)丙二腈与不同的双亲核试剂的反应导致以良好的产率形成具有邻苯二甲醚环系统的螺杂环。

  DOI：

  10.3184/174751917x14944355549159
• 作为产物：
  描述：

  在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以84%的产率得到2-(3-oxoisobenzofuran-1(3H)-ylidene)malononitrile
  参考文献：
  名称：

  A new anhydride analog

  摘要：

  A novel imide-forming reaction is described in which 3-(dicyanomethylidene) phthalide (pseudoanhydride) reacts with amines at room temperature. The pseudoanhydride was synthesized by condensation of phthalic anhydride with malononitrile followed by treatment with phosphrous oxychloride.

  DOI：

  10.1016/0040-4039(91)80803-e

文献信息

• Reactions of Heterocyclic Ketene Aminals with 2-[3-Oxoisobenzofuran-1(3H)-ylidene]malononitrile: Synthesis of Novel Polyfunctionalized 1,4-Dihydropyridine-Fused 1,3-Diazaheterocycles
  作者：Jing-Kui Yang、Zhi-Tang Huang、Chu-Yi Yu、Wen-Yuan Xu、Yue-Mei Jia

  DOI：10.1055/s-0029-1220126

  日期：2010.7

  An efficient method has been developed for the synthesis of a novel kind of polyfunctionalized 1,4-dihydropyridine-fused 1,3-diazaheterocycles via the reactions of heterocyclic ketene aminals (HKAs) with 2-[3-oxoisobenzofuran-1(3H)-ylidene]malono­nitrile.

  通过杂环烯酮胺（HKAs）与 2-[3-氧代异苯并呋喃-1(3H)-亚基]丙二腈的反应，开发了一种合成新型多官能度 1,4- 二氢吡啶融合 1,3- 二氮杂环的有效方法。
• 一种ITIC衍生物的新型合成方法
  申请人：武汉理工大学

  公开号：CN108864142A

  公开（公告）日：2018-11-23

  本发明提供一种ITIC衍生物的新型合成方法，包括如下步骤：步骤1、取一个干净的烧瓶，将适量IDTT‑DM‑CHO溶解于氯仿溶液中；步骤2、向步骤1所得混合液中加入INCN衍生物，缓慢滴加一定量的吡啶，用氮气鼓泡20‑30min；步骤3、将鼓泡完的混合液密封，80℃回流12‑14h，将溶剂旋干得到粗产物；步骤4、向粗产物中加入二氯甲烷溶解，加硅胶旋干，用柱色谱法分离，随后用甲醇洗涤分离产物，得到ITIC衍生物。本发明方法采用一锅法，实验操作过程简单，副反应较少，反应程度比较彻底，粗产物纯度高，提纯过程简单，溶剂消耗较小，复合绿色化学的理念。
• Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs
  作者：Nan-Yang Chen、Li-Ping Ren、Min-Ming Zou、Zhi-Ping Xu、Xu-Sheng Shao、Xiao-Yong Xu、Zhong Li

  DOI：10.1016/j.cclet.2013.12.004

  日期：2014.2

  Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with Spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper. (C) 2013 Xu-Sheng Shao and Zhong Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• A synthesis of functionalized spiro isobenzofuran-1,6′-[1,3] thiazines from phthalic anhydride-malononitrile adduct and ammonium carbamodithioates
  作者：Mohammad Hadi Diyanatizadeh、Issa Yavari

  DOI：10.1080/17415993.2015.1089439

  日期：2016.1.2

  The reaction of 2-[3-oxo-isobenzofuran-1(3H)-ylidene]malononitrile, generated from phthalic anhydride and malononitrile, with ammonium alky(aryl)carbamodithioates, leading to the formation of functionalized spiro isobenzofuran-1,6'-[1,3] thiazine systems, in good yields, is reported.[GRAPHICS]Highlights The reaction of 2-[3-oxo-isobenzofuran-1(3H)-ylidene]malononi trile, with ammonium alky(aryl)carbamodithioates, leads to the formation of functionalized spiro isobenzofuran-1,6'-[1,3]thiazine systems, in good yields.
• ORGANIC SEMICONDUCTING COMPOUNDS
  申请人：FLEXENABLE LTD

  公开号：US20220131078A1

  公开（公告）日：2022-04-28

  The invention relates to novel organic semiconducting compounds containing a polycyclic unit, to methods for their preparation and educts or intermediates used therein, to compositions, polymer blends and formulations containing them, to the use of the compounds, compositions and polymer blends as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photodetectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD, OFET and OLED devices comprising these compounds, compositions or polymer blends.