(E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene | 21071-42-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene
• 英文别名: 1-[(E)-2-(2,5-dimethoxy-4-methylphenyl)ethenyl]-2,5-dimethoxy-4-methylbenzene
• CAS: 21071-42-1
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: WJICHCPOPKDEQM-BQYQJAHWSA-N

物化性质

• 沸点：
  474.2±40.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene 在 dimethyl sulfide borane 、 Orange CRET^+. 作用下， 以 二氯甲烷 为溶剂， 反应 0.3h， 以97%的产率得到1,2-bis(2,5-dimethoxy-p-tolyl)ethane
  参考文献：
  名称：

  Efficient Hydrogenation of Sterically Hindered Olefins with Borane−Methyl Sulfide Complex

  摘要：

  Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the borane-methyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the EMS complex (in the absence of a one-electron oxidant) is also carried out-in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.

  DOI：

  10.1021/jo960357e
• 作为产物：
  描述：

  2,5-二甲氧基-4-甲苯甲醛 在 titanium(III) chloride 、 lithium 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以34%的产率得到(E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene
  参考文献：
  名称：

  双（生物还原）烷基化剂：在裸鼠人癌模型中的合成和生物活性。

  摘要：

  描述了导致具有构象受限和可移动间隔区的双（生物还原）烷基化剂的化学研究。具有构象可移动的乙烯间隔基的两个靶，即2,2'-亚乙基双[6-（羟甲基）-对苯醌]二乙酸酯（3b）和2,2'-亚乙基双[6-（溴甲基）-对苯醌] [3c]，是使用已建立的上皮/伯基特淋巴瘤杂交细胞系（D98 / HR1）在体内和体外进行研究的，该系先前已显示出可在裸鼠中诱发癌症。两种测试化合物在体外均无活性，这些细胞在体外对测试药物的相对抗性，以及双（溴甲基）类似物在体内的选择性抗肿瘤特性，导致该化合物在低氧环境中经历了生物还原成烷基化反应的提议。肿瘤的核心

  DOI：

  10.1021/jm00366a004

文献信息

• Anti-cancer agents and processes for their preparation
  申请人：The Ohio State University Research Foundation

  公开号：US04683087A1

  公开（公告）日：1987-07-28

  Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are either two hydrogen atoms or together form a methylene group, and each X is a bromo, iodo or tosyloxy group and the dotted bonds indicate that the central linkage is attached to the two phenyl rings at positions which are either meta to both CH.sub.2 X groups or para to both such groups, possess anti-cancer activity. The active compounds are prepared by multi-step syntheses beginning with dimethoxymethylbenzaldehydes or di(hydroxymethyl)methoxyphenols; many of the intermediates involved are themselves novel.

  具有以下结构的化合物##STR1##其中R.sub.1和R.sub.2可以是两个氢原子，也可以一起形成一个亚甲基基团，每个X是溴、碘或对甲苯磺酰氧基团，虚线键表示中心连接部分连接到两个苯环的位置，这些位置要么是对于两个CH.sub.2 X基团，要么是对于两个这样的基团的间位，具有抗癌活性。这些活性化合物是通过多步合成制备的，起始物是二甲氧基甲基苯甲醛或二(羟甲基)甲氧基酚；其中许多中间体本身是新颖的。
• Acid Catalysis vs. Electron-Transfer Catalysis via Organic Cations or Cation-Radicals as the Reactive Intermediate. Are These Distinctive Mechanisms?
  作者：Rajendra Rathore、Jay K. Kochi、Augusto Canavesi、Larry L. Miller、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0114

  日期：——

  Proton transfer to aromatic and olefinic donors (D) lends to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide.-pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions, However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of sepal ate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories.
• US4683087A
  申请人：——

  公开号：US4683087A

  公开（公告）日：1987-07-28
• Efficient Hydrogenation of Sterically Hindered Olefins with Borane−Methyl Sulfide Complex
  作者：R. Rathore、U. Weigand、J. K. Kochi

  DOI：10.1021/jo960357e

  日期：1996.1.1

  Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the borane-methyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the EMS complex (in the absence of a one-electron oxidant) is also carried out-in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.
• Bis(bioreductive) alkylating agents: synthesis and biological activity in a nude mouse human carcinoma model
  作者：Donald T. Witiak、Prabhakar L. Kamat、Debra L. Allison、Stephen M. Liebowitz、Ronald Glaser、Jane E. Holliday、Melvin L. Moeschberger、Joseph P. Schaller

  DOI：10.1021/jm00366a004

  日期：1983.12

  hybrid cell line (D98/HR1) previously shown to induce carcinomas in nude mice. Inactivity of both test compounds in vitro, the relative resistance of these cells to test drugs in vitro, and the selective antitumor properties of the bis(bromomethyl) analogue in vivo lead to the proposal that this compound undergoes bioreduction to an alkylating species in the hypoxic core of the tumor, thereby exerting

  描述了导致具有构象受限和可移动间隔区的双（生物还原）烷基化剂的化学研究。具有构象可移动的乙烯间隔基的两个靶，即2,2'-亚乙基双[6-（羟甲基）-对苯醌]二乙酸酯（3b）和2,2'-亚乙基双[6-（溴甲基）-对苯醌] [3c]，是使用已建立的上皮/伯基特淋巴瘤杂交细胞系（D98 / HR1）在体内和体外进行研究的，该系先前已显示出可在裸鼠中诱发癌症。两种测试化合物在体外均无活性，这些细胞在体外对测试药物的相对抗性，以及双（溴甲基）类似物在体内的选择性抗肿瘤特性，导致该化合物在低氧环境中经历了生物还原成烷基化反应的提议。肿瘤的核心