1,2-二乙烯基苯 | 91-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-二乙烯基苯
• 英文名称: 1,2-divinylbenzene
• 英文别名: divinylbenzene；o-divinylbenzene；1,2-bis(ethenyl)benzene
• CAS: 91-14-5
• 化学式: C₁₀H₁₀
• mdl: MFCD00010654
• 分子量: 130.189
• InChiKey: MYRTYDVEIRVNKP-UHFFFAOYSA-N

物化性质

• 熔点：
  30.2 °C
• 沸点：
  175.9°C (rough estimate)
• 密度：
  0.9325
• 物理描述：
  Divinyl benzene appears as a water-white to straw colored liquid. Slightly less dense than water and insoluble in water. Vapors may be toxic. Used in making rubber.
• 颜色/状态：
  Pale, straw-colored liquid.
• 闪点：
  57 °C (Cleveland open-cup) /DVB-22/
• 溶解度：
  In water, 52 mg/l @ 25 °C /Estimated/
• 蒸汽密度：
  Relative vapor density (air = 1): 4.48
• 蒸汽压力：
  VP: 0.579 mm Hg @ 25 °C /m-Divinylbenzene/ /Extrapolated/
• 自燃温度：
  500 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes
• 聚合：
  Hazardous polymerization may occur. ... Usually contains inhibitors to prevent polymerization. Uninhibited monomer vapor may form polymer in vents and other confined spaces.
• 气味阈值：
  As with other styrene monomers, the odor can be detected by humans at levels below dangerous concn, ie, 10-60 ppm.
• 保留指数：
  1102

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

乙烯基苯在结构上与苯乙烯相似，很可能会通过相同的代谢途径进行生物转化。

Divinyl benzene is structurally similar to styrene and is likely to be biotransformed by the same metabolic pathways.

来源:Hazardous Substances Data Bank (HSDB)

代谢

雌性Wistar大鼠单次腹腔注射二乙烯基苯（DEB）300mg/kg。二乙烯基苯被广泛氧化成亲电环氧环，该环被谷胱甘肽攻击形成结合物，这些结合物通过巯基酸途径进一步代谢生成巯基酸。另一个重要的途径涉及环氧水解酶催化的环氧环的水合作用，形成一种糖醇，该糖醇进一步氧化代谢成乙烯基扁桃酸、乙醛酸和苯甲酸。一个次要的代谢途径涉及环氧环重排为乙烯基苯乙醛。单次腹腔注射1,4-二乙烯基苯的大鼠将近5.6%的剂量以甘氨酸结合物形式排出，无论给予的剂量如何。随着初始剂量的增加，总硫醚分数显著降低，在100、200和300mg/kg剂量时分别占剂量的23、17和12%。

... Female Wistar-rats were given a single intraperitoneal (ip) dose of diethenylbenzene (DEB) at 300mg/kg. Diethenylbenzene was extensively oxidized to an electrophilic oxirane which was attacked by glutathione forming conjugates which were further metabolized through the mercapturic-acid pathway to form mercapturic acids. Another important pathway involved the epoxide-hydrolase catalyzed hydration of the oxirane forming a glycol which was further oxidatively metabolized to ethenyl mandelic, glyoxylic and benzoic acids. A minor metabolic pathway involved the rearrangement of the oxirane to an ethenyl phenylacetaldehyde. Rats given a single ip dose of 1,4-diethenylbenzene excreted nearly 5.6 percent of the dose as the glycine conjugate, regardless of the dose given. The total thioether fraction decreased significantly with increasing initial doses accounting for 23, 17, and 12 percent of the doses at 100, 200, and 300mg/kg, respectively.

来源:Hazardous Substances Data Bank (HSDB)

代谢

... 成年雌性Wistar大鼠通过腹腔注射100、200或300mg/kg的diethenylbenzene (DEB)。... 主要识别出的代谢物是3-ethenylphenylglyoxylic acid（3-乙烯基苯甲酸）、3-ethenylmandelic acid（3-乙烯基扁桃酸）、N-acetyl-S-(2-(3-ethenylphenyl)-2-hydroxyethyl)-L-cysteine（N-乙酰-S-(2-(3-乙烯基苯基)-2-羟基乙基)-L-半胱氨酸）和N-acetyl-S-(1-(3-ethenylphenyl)-2-hydroxyethyl)-L cysteine（N-乙酰-S-(1-(3-乙烯基苯基)-2-羟基乙基)-L-半胱氨酸）。... 以剂量的百分比表示的总硫醚排泄量在100mg/kg后为32.5%，在200mg/kg后为25.3%，在300mg/kg DEB后为27.1%。

... Adult female Wistar-rats were injected intraperitoneally with 100, 200, or 300mg/kg diethenylbenzene (DEB). ... The major identified metabolites were 3-ethenylphenylglyoxylic-acid, 3-ethenylmandelic-acid, N-acetyl-S-(2-(3-ethenylphenyl)-2-hydroxyethyl)-L-cysteine, and N-acetyl-S-(1-(3-ethenylphenyl)-2-hydroxyethyl)-L cysteine. ... Total thioether excretion expressed as a percentage of the dose was 32.5% after 100mg/kg, 25.3% after 200mg/kg, and 27.1% after 300mg/kg DEB.

来源:Hazardous Substances Data Bank (HSDB)

代谢

关于二乙烯苯的潜在致癌性存在担忧，因为它可以被细胞色素P450氧化成苯乙烯-7,8-环氧化物。

There is concern about the potential carcinogenicity of divinyl benzene because it can be oxidized by cytochrome P450 to styrene-7,8-epoxide.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该物质可以通过吸入其蒸气被身体吸收。

The substance can be absorbed into the body by inhalation of its vapour.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，吞食，皮肤和/或眼睛接触

inhalation, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛、皮肤、呼吸系统刺激；皮肤烧伤；在动物中：中枢神经系统抑制

irritation eyes, skin, respiratory system; skin burns; In Animals: central nervous system depression

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 吸入症状

咳嗽。喉咙痛。

Cough. Sore throat.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

红色。

Redness.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,2-二乙烯基苯 在 吡啶 、 copper diacetate 、 potassium tert-butylate 、 溴 作用下， 生成 4b,5,5a,6,10b,11,11a,12-octahydro-indeno[1,2-b]fluorene
  参考文献：
  名称：

  722.大环炔化合物。第二部分 1,2：7,8-二苯并环十二烷基-1,7-二烯-3,5,9,11-丁炔

  摘要：

  DOI：

  10.1039/jr9600003614
• 作为产物：
  描述：

  2-[2-(2-羟基乙基)苯基]乙醇 在 氢氧化钾 作用下， 185.0 ℃ 、8.0 kPa 条件下， 生成 1,2-二乙烯基苯
  参考文献：
  名称：

  o-Phenylenediacetimide and other Compounds Related to 3, 1H-Benzazepine

  摘要：

  DOI：

  10.1021/jo50012a012
• 作为试剂：
  描述：

  在 1,2-二乙烯基苯 、 硫酸 作用下， 生成 1,3-二乙酰基苯 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Molecular recognition on synthetic amorphous surfaces. The influence of functional group positioning on the effectiveness of molecular recognition

  摘要：

  DOI：

  10.1021/ja00265a046

文献信息

• Metal-Free-Catalyzed Synthesis of Allyl Nitriles via C_sp²–C_sp³ Coupling between Olefins and Azobis (Alkyl-carbonitrile)
  作者：Zhong-zhong Cao、Zhiwen Nie、Tonglin Yang、Miaodong Su、Hui Li、Wei-ping Luo、Qiang Liu、Can-Cheng Guo

  DOI：10.1021/acs.joc.9b03127

  日期：2020.3.6

  The metal-free-catalyzed synthesis of allyl nitriles from Csp2-Csp3 coupling between olefins and azobis was carried out. Key on this work was that the synthesis of allyl nitriles directly using olefin as a starting material was considered to be more efficient and economical than the alkyne, alkynyl carboxylic acid, or cinnamic acid used in previous works. Moreover, in this reaction, iodine served as

  由烯烃和偶氮二之间的Csp2-Csp3偶联进行了无金属催化的烯丙基腈的合成。这项工作的关键在于，直接使用烯烃作为起始原料合成烯丙基腈被认为比先前工作中使用的炔烃，炔基羧酸或肉桂酸更有效，更经济。此外，在该反应中，碘是唯一的促进剂，偶氮二bis是氰化试剂，N2是唯一的无毒副产物，可以避免利用金属催化剂和有毒的腈试剂并避免产生有毒废物。在最佳条件下，已经以良好至极好的收率合成了30多种所需产物，包括芳族和脂族腈。根据对照实验和文献数据，
• Visible-Light-Mediated Annulation of Electron-Rich Alkenes and Nitrogen-Centered Radicals from <i>N</i>-Sulfonylallylamines: Construction of Chloromethylated Pyrrolidine Derivatives
  作者：Lorène N. S. Crespin、Andreas Greb、David C. Blakemore、Steven V. Ley

  DOI：10.1021/acs.joc.7b02146

  日期：2017.12.15

  A visible-light-mediated annulation of N-sulfonylallylamines and olefins is reported. Rapid access to highly functionalized chloromethylated pyrrolidines can be achieved using mild conditions for the generation of nitrogen-centered radicals. Both a transition-metal-based catalyst and an organic dye can be used as photosensitizers with 0.5 mol % loading. The reaction was found to be applicable to a

  报道了N-磺酰基烯丙基胺和烯烃的可见光介导的环化。使用温和条件生成氮中心自由基可以快速获得高度官能化的氯甲基化吡咯烷。过渡金属基催化剂和有机染料都可以用作具有0.5 mol％负载量的光敏剂。发现该反应适用于多种富电子和电子中性的烯烃。
• Ultrasound-assisted tandem synthesis of tri- and tetra-substituted pyrrole-2-carbonitriles from alkenes, TMSCN and N,N-disubstituted formamides
  作者：Qing-Wen Gui、Fan Teng、Sheng-Neng Ying、Yang Liu、Tao Guo、Jian-Xin Tang、Jin-Yang Chen、Zhong Cao、Wei-Min He

  DOI：10.1016/j.cclet.2020.07.017

  日期：2020.12

  An energy-saving and eco-friendly method for the efficient construction of various tri- and tetra-substituted pyrrolecarbonitriles through ultrasound-assisted multicomponent tandem reaction of readily available alkenes, TMSCN and N,N-disubstituted formamides within 40 min under metal-, solvent-free and mild conditions was developed. The dual role of iodine (catalyst and oxidant) notably simplified the

  摘要一种通过节能，环保的方法，通过在金属，开发了无溶剂和温和的条件。碘（催化剂和氧化剂）的双重作用显着简化了反应条件并减少了产生的化学废物
• Efficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO₂ and TEMPO
  作者：Soham Maity、Srimanta Manna、Sujoy Rana、Togati Naveen、Arijit Mallick、Debabrata Maiti

  DOI：10.1021/ja311942e

  日期：2013.3.6

  common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations

  硝基烯烃是一种常见且用途广泛的试剂。它从烯烃合成通常受到顺式和反式化合物混合物的形成的限制。在这里，我们报告亚硝酸银 (AgNO2) 与 TEMPO 一起可以促进范围广泛的烯烃的区域和立体选择性硝化。这项工作公开了一种新的有效方法，其中从烯烃开始，硝基烷烃自由基形成和随后的转化以立体选择性方式导致所需的硝基烯烃。
• The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem Three-Component Reaction
  作者：Xue-Qing Mou、Zheng-Liang Xu、Li Xu、Shao-Hua Wang、Bang-Hong Zhang、Di Zhang、Jie Wang、Wei-Ting Liu、Wen Bao

  DOI：10.1021/acs.orglett.6b01883

  日期：2016.8.19

  N-disubstituted formamide, has been developed to give a series of multisubstituted pyrroles in moderate to good yields with high regioselectivities. This reaction not only reveals a new reaction mode for α-aminonitriles, but also provides a new and efficient cyclization pattern for the synthesis of multisubstituted pyrroles as well as their derivatives, which might facilitate related biological studies

  已经开发出空前的碱性化学物质的亲核加成/环化/芳构化级联，即芳族烯烃/炔烃，三甲基甲硅烷基氰化物和N，N-二取代甲酰胺，以中等收率和良好收率和高区域选择性提供了一系列多取代吡咯。该反应不仅揭示了α-氨基腈的新反应方式，而且为多取代吡咯及其衍生物的合成提供了新的有效的环化模式，这可能有助于相关的生物学研究。