(1,2-dimethoxyethane-1,1-diyl)dibenzene | 3461-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1,2-dimethoxyethane-1,1-diyl)dibenzene
• 英文别名: Benzene, 1,1'-(1,2-dimethoxyethylidene)bis-；(1,2-dimethoxy-1-phenylethyl)benzene
• CAS: 3461-40-3
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: DZVRIIUGDPGKMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为产物：
  描述：

  1,1-二苯乙烯 在 tetrabutylammonium tetrafluoroborate 、 氧气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到(1,2-dimethoxyethane-1,1-diyl)dibenzene
  参考文献：
  名称：

  Electrochemical Difunctionalization of Styrenes via Chemoselective Oxo-Azidation or Oxo-Hydroxyphthalimidation

  摘要：

  DOI：

  10.1021/acs.orglett.1c02991

文献信息

• Electrochemical Difunctionalization of Alkenes by a Four‐Component Reaction Cascade Mumm Rearrangement: Rapid Access to Functionalized Imides
  作者：Xiaofeng Zhang、Ting Cui、Xin Zhao、Ping Liu、Peipei Sun

  DOI：10.1002/anie.201913332

  日期：2020.2.24

  transfer. Inexpensive, commercially available arylethylenes, aryl or heterocyclic acids, acetonitrile, and alcohols were used as substrates. A wide range of aryl acids and alcohols were tolerated and provided imides in satisfactory yields. Subsequent hydrolysis of imides could be utilized to synthesize valuable amides and β-amino alcohol derivatives.

  电化学四组分反应级联Mumm重排的发展。它是原位生成O-酰基异酰胺用于1,3-（O→N）酰基转移的罕见例子。廉价的市售芳基乙烯，芳基或杂环酸，乙腈和醇用作底物。耐受各种芳基酸和醇，并以令人满意的产率提供酰亚胺。随后酰亚胺的水解可用于合成有价值的酰胺和β-氨基醇衍生物。
• Substrate‐Dependent Electrochemical Dimethoxylation of Olefins
  作者：Sheng Zhang、Lijun Li、Ping Wu、Pengjuan Gong、Rui Liu、Kun Xu

  DOI：10.1002/adsc.201801173

  日期：2019.2

  A general and direct electrochemical dimethoxylation of olefins is reported, which enables a divergent route to different products depending on the structure of olefins. The present protocol features mild conditions and broad substrate scope (49 examples) obviating the usage of transtion‐metals and external oxidants. More importantly, to rationalize the divergent route of the transformation, an ionic‐like

  报道了烯烃的一般和直接的电化学二甲氧基化，其使得可以根据烯烃的结构而分歧地通往不同的产物。本协议具有温和的条件和广泛的底物范围（49个实例），从而避免了使用过渡金属和外部氧化剂。更重要的是，为了合理化转化的发散途径，提出了一种涉及碳正离子中间体的离子样途径，并且多样化的产物归因于碳正离子的不同稳定性。
• ELECTROCHEMICAL OXIDATION OF AROMATIC OLEFINS. DEPENDENCE OF THE REACTION COURSE ON THE STRUCTURE OF THE OLEFINS AND ON THE NATURE OF THE ANODES
  作者：Masanobu Kojima、Hirochika Sakuragi、Katsumi Tokumaru

  DOI：10.1246/cl.1981.1707

  日期：1981.12.5

  Anodic oxidation of a series of substituted styrenes was investigated in methanol with a platinum and a graphite electrode. Use of the platinum anode gave mainly dimethoxylated monomers accompanied with one or more of three types of dimethoxylated dimers (αα-, αβ-, and ββ-dimers) depending on the substituents. Use of the graphite anode, however, afforded the ββ-dimers as the main product together with

  用铂和石墨电极在甲醇中研究了一系列取代苯乙烯的阳极氧化。根据取代基的不同，铂阳极的使用主要产生二甲氧基化单体，并伴有三种类型的二甲氧基化二聚体（αα-、αβ-和ββ-二聚体）中的一种或多种。然而，石墨阳极的使用提供了作为主要产物的 ββ-二聚体以及二甲氧基化单体。
• Photochemical Electron-transfer Reaction between Aromatic Olefins and Metal Ions. Dependence of the Reaction Course on the Structure of the Olefins
  作者：Masanobu Kojima、Hirochika Sakuragi、Katsumi Tokumaru

  DOI：10.1246/bcsj.58.521

  日期：1985.2

  To investigate the photochemical electron transfer from aromatic olefins to copper(II) or iron(III) ions, a series of substituted styrenes (1) was irradiated in the presence of copper(II) or iron(III) salts in methanol, which gave dimethoxylated monomers (2) and one or more of three types of dimethoxylated dimers [α,α- (3), α,β- (4), and β,β,-dimers (5)]. The formation of these products are reasonably

  为了研究从芳族烯烃到铜 (II) 或铁 (III) 离子的光化学电子转移，在甲醇中存在铜 (II) 或铁 (III) 盐的情况下照射一系列取代的苯乙烯 (1)，得到二甲氧基化单体(2)和三种二甲氧基化二聚体[α,α-(3)、α,β-(4)和β,β,-二聚体(5)]中的一种或多种。这些产物的形成合理地归因于通过电子从受激烯烃转移到金属离子而产生的烯烃的阳离子自由基的参与。发现底物上的取代基控制反应产物。
• The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in methanol. Homolytic cleavage versus electron-transfer pathways
  作者：Dino Mangion、Donald R. Arnold

  DOI：10.1139/cjc-77-10-1655

  日期：——

  The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6 pi-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.