dicyanomethylene-4,4'-dimethylbenzophenone | 82074-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dicyanomethylene-4,4'-dimethylbenzophenone
• 英文别名: 2-(di-p-tolylmethylene)malononitrile；<4,4'-Dimethyl-benzhydryliden>-malonsaeure-dinitril；Propanedinitrile, [bis(4-methylphenyl)methylene]-；2-[bis(4-methylphenyl)methylidene]propanedinitrile
• CAS: 82074-10-0
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: PCOLLFCUIBQUOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-庚酮 、 dicyanomethylene-4,4'-dimethylbenzophenone 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-methyl-2-n-pentyl-3,3-di(p-methylphenyl)-4-cyano-5-amino-2,3-dihydrofuran
  参考文献：
  名称：

  Facile Synthesis of Polysubstituted 2,3-Dihydrofuran and Cyclopentenylamine Derivatives Promoted by Samarium Diiodide

  摘要：

  The intermolecular reductive coupling of 1,1-diaryl-2,2-dicyanoethylenes or 1,1-diaryl-2-cyano-2-ethoxycarbonylethylenes with ketones or chalcones induced by samarium (II) iodide was studied. Functionalized 2,3-dihydrofuran and cyclopentenylamine derivatives were prepared in moderate to good yields under neutral and mild conditions.

  DOI：

  10.1081/scc-120021985
• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 、 丙二腈 在 乙酸铵 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 dicyanomethylene-4,4'-dimethylbenzophenone
  参考文献：
  名称：

  Mass spectra of dicyanomethylene derivatives of benzophenone analogs

  摘要：

  AbstractThe dicyanomethylene derivative of a benzophenone analog significantly alters the fragmentation pattern observed during electron impact ionization of the underivatized parent compound. A double bond connecting the dicyanomethylene moiety to the parent compound is cleaved during a major fragmentation pathway for many of these compounds. A mechanism involving rearrangement of two hydrogen atoms is proposed to rationalize cleavage of this double bond. Conventional mass spectra as well as collisionally activated dissociation mass spectra of selected ions of several model compounds are reported and described in support of a proposed fragmentation mechanism.

  DOI：

  10.1002/oms.1210181102

文献信息

• Synthesis of Functionalized 2,3-Dihydropyrroles Promoted by Samarium Diiodide
  作者：Xiaoliang Xu、Yongmin Zhang

  DOI：10.1081/scc-120017131

  日期：2003.1.5

  Abstract The intermolecular reductive coupling of 1,1-diaryl-2,2-dicyanoethylenes or 1,1-diaryl-2-cyano-2-ethoxycarbonylethylenes with substituted benzalazines induced by samarium diiodide was studied. Functionalized 2,3-dihydropyrroles were prepared in good yields under neutral and mild conditions.

  摘要 研究了二碘化钐诱导的1,1-二芳基-2,2-二氰基乙烯或1,1-二芳基-2-氰基-2-乙氧基羰基乙烯与取代苯扎嗪的分子间还原偶联。在中性和温和条件下以良好的收率制备了功能化的 2,3-二氢吡咯。
• Transformation of<i>gem</i>-Dicyanoethenes by Samarium: Direct Formation of Indenes or Direct Decyanation with in Situ Disilylation
  作者：Yongjun Liu、Fuqiang Zhang、Yan Qi、Yongmin Zhang、Shusheng Zhang

  DOI：10.1002/ejoc.200800258

  日期：2008.11

  Intramolecular cyclization of 1,1-diaryl-2,2-dicyanoethenes promoted by samarium metal in DMF in the presence of TMSCl allowed direct construction of the indene core, whereas 1-alkyl-1-aryl-2,2-dicyanoethenes underwent intermolecular coupling cyclization and decyanation under the same conditions. Simultaneously, disilylation occurred at the amino moiety resulting from the reduction of the cyano group

  在 TMSCl 存在下，由钐金属在 DMF 中促进的 1,1-二芳基-2,2-二氰乙烯分子内环化允许直接构建茚核，而 1-烷基-1-芳基-2,2-二氰乙烯进行分子间偶联在相同条件下进行环化和脱氰。同时，由于氰基还原，氨基部分发生二甲硅烷基化。然而，当存在微量水时，仅观察到 C=C 键的简单还原。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• Polarizing plate protective film, polarizing plate and liquid crystal display device
  申请人：Murakami Takashi

  公开号：US20080049324A1

  公开（公告）日：2008-02-28

  A polarizing plate protective film comprising a cellulose ester, and a saccharide ester compound in which all or a part of OH groups in Compound (A) or in Compound (B) are esterified, wherein Compound (A) consists of one of a furanose structure and a pyranose structure, and Compound (B) consists of two to twelve of at least one type of a furanose structure and a pyranose structure which are bonded in Compound (B); wherein the polarizing plate protective film exhibits Ro of 0-10 nm and Rt of −30 to +20 nm.

  一种极化片保护膜，包括纤维素酯和一种糖酯化合物，其中化合物（A）或化合物（B）中的全部或部分OH基团被酯化，化合物（A）由呋喃糖或吡喃糖结构中的一种组成，化合物（B）由化合物（B）中至少一种呋喃糖或吡喃糖结构的两到十二个组成，这些结构在化合物（B）中被结合；其中，极化片保护膜的Ro值为0-10 nm，Rt值为-30到+20 nm。
• Cellulose Acylate Film, Method of Producing the Same, Cellulose Derivative Film, Optically Compensatory Film Using the Same, Optically-Compensatory Film Incorporating Polarizing Plate, Polarizing Plate and Liquid Crystal Display Device
  申请人：Haruta Hiromoto

  公开号：US20090290100A1

  公开（公告）日：2009-11-26

  A method of producing a cellulose derivative film, the method comprising: forming a film with a solvent cast method from a dope including a cellulose derivative satisfying following conditions (a) and (b): (a) at least one among three hydroxyl groups included in a glucose unit of cellulose is substituted by a substituent of which a polarizability anisotropy Δα represented as following Expression (1) is 2.5×10 −24 cm 3 or higher: Expression (1): Δα=αx−(αy+αz)/2, wherein αx, αy and αz is as defined in the specification; and (b) when a substitution degree by a substituent of which Δα is 2.5×10 −24 cm 3 or higher is P A , and a substitution degree by a substituent of which Δα is lower than 2.5×10 −24 cm 3 is P B , the P A and P B satisfy following Expressions (3) and (4): Expression (3): 2P A +P B >3.0; and Expression (4): P A >0.2.

  一种生产纤维素衍生物薄膜的方法，该方法包括：使用包括满足以下条件（a）和（b）的纤维素衍生物的溶胶，通过溶剂浇铸法形成薄膜：（a）纤维素的葡萄糖单元中的三个羟基中的至少一个被取代为极化率各向异性Δα（以下表达式（1）表示）为2.5×10-24cm3或更高的取代基：表达式（1）：Δα=αx-（αy+αz）/ 2，其中αx，αy和αz如规范中定义的；并且（b）当Δα为2.5×10-24cm3或更高的取代基的取代度为PA时，Δα低于2.5×10-24cm3的取代基的取代度为PB，PA和PB满足以下表达式（3）和（4）：表达式（3）：2PA + PB> 3.0；表达式（4）：PA> 0.2。
• Meerwein Arylation of Aryl(alkyl)idenemalononitriles and Diazonium Salts for the Synthesis of 2-(Aryl(alkyl)/arylmethylene)malononitrile Derivatives
  作者：Xiaoqing Lv、Shengjun Liu、Yu Guo、Lijiu Gao、Liming Zhao、Jinpeng Zhang、Liangce Rong

  DOI：10.1021/acs.joc.3c01161

  日期：2023.9.1

  arylation reaction from aryl(alkyl)idenemalononitriles and diazonium salts for the synthesis of 2-(aryl(alkyl)/arylmethylene)malononitrile derivatives under mild conditions was well developed. Different from the general addition reactions between alkenes and diazonium salts, this study performed the traditional coupling reaction for the formation of C(sp2)–C(sp2) bond arylation products. The radical reaction

  在温和条件下，由芳基（烷基）亚甲基丙二腈和重氮盐合成2-（芳基（烷基）/芳基亚甲基）丙二腈衍生物的无金属Meerwein芳基化反应得到了很好的发展。与一般的烯烃与重氮盐之间的加成反应不同，本研究进行了传统的偶联反应，形成C(sp 2 )–C(sp 2 )键芳基化产物。自由基反应机理在对照实验中得到了很好的验证。该方法的其他优点是底物范围广和良好的群体耐受性。此外，所得产物可以很容易地转化为高价值的不对称酮和加氢反应。