1,4-二溴-2,3-环氧丁烷 | 14396-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 1,4-二溴-2,3-环氧丁烷
• 英文名称: 1,4-dibromo-2,3-epoxybutane
• 英文别名: 1,4-Dibrom-2,3-epoxybutan；2,3-bis(bromomethyl)oxirane
• CAS: 14396-64-6
• 化学式: C₄H₆Br₂O
• 分子量: 229.899
• InChiKey: RBAKDFDWMGKHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-二溴-2,3-环氧丁烷 在 sulfur tetrafluoride 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-Dibrom-2,4-difluorbutan
  参考文献：
  名称：

  Golikov,V.I. et al., Soviet progress in chemistry, 1975, vol. 41, # 5, p. 46 - 49

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到1,4-二溴-2,3-环氧丁烷
  参考文献：
  名称：

  Enhancement of Bacterial Mutagenicity of Bifunctional Alkylating Agents by Expression of Mammalian Glutathione S-Transferase

  摘要：

  Recently, we inserted the plasmid vector pKK233-2 containing rat GSH S-transferase (GST) 5-5 cDNA into Salmonella typhimurium TA1535 and found that these bacteria [GST 5-5(+)] expressed the protein and produced mutations when ethylene or methylene dihalides were added [Thier, R., Taylor, J. B., Pemble, S. E., Ketterer, B., Persmark, M., Humphreys, W. G., and Guengerich, F. P. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 8576-85803. After exposure to the known GST 5-5 substrate 1,2-epoxy-3-(4'-nitrophenoxy)propane, the GST 5-5(+) strain showed fewer mutants than the bacteria transfected with the cDNA clone in a reverse orientation [GST 5-5(-)], suggesting a protective role of GST 5-5. However, mutations were considerably enhanced in the GST 5-5(+) strain [as compared to GST 5-5(-)] when 1,2,3,4-diepoxybutane (butadiene diepoxide) or 1,2-epoxy-4-bromobutane was added. The GST 5-5(+) and GST 5-5(-) bacterial stains showed similar responses to 1,2-epoxypropane, 3,4-epoxy-1-butene, and 1,4-dibromobutane. The results suggest that some bifunctional activated butanes are transformed to mutagenic products through GSH conjugation. We also found that the GST 5-5(-) strain showed enhanced mutagenicity with 1,4-dibromo-2,3-epoxybutane, 1,2-epoxy-3-bromopropane (epibromohydrin), and (+)-1,4-dibromo-2,3-dihydroxybutane. The possibility was considered that a 5-membered thialonium ion may be involved in the mutagenicity. Model thialonium compounds were rather stable to hydrolysis in aqueous solution at pH 7.4 and slowly alkylated 4-(4-nitrobenzyl)pyridine. The presence of a hydroxyl group beta to the sulfur did not enhance reactivity. Mechanisms involving episulfonium ions are considered more likely. Potential. oxidation products of the toxic pesticide 1,2-dibromo-3-chloropropane (DBCP) were also considered in this system. DBCP itself gave rather similar results in the two strains. Others have reported that oxidation of DBCP is required for mutagenicity, along with GST-catalyzed GSH conjugation [Simula, T. P., Glancey, M. J., Soderlund, E. J., Dybing, E., and Wolf, C. R. (1993) Carcinogenesis 14, 2303-2307]. The putative oxidation product 1,2-dibromopropional did not show a difference between the two strains. However, 1,3-dichloroacetone, a model for the putative oxidation product l-bromo-3-chloroacetone, was considerably more mutagenic in the GST 5-5(+) strain.

  DOI：

  10.1021/tx00045a019

文献信息

• Intramolecular reactions of allyloxy radicals featuring six-centred transition states; Regiochemistry and stereochemistry.
  作者：Michael J. Begley、Neil Housden、Amanda Johns、John A. Murphy

  DOI：10.1016/s0040-4020(01)96183-6

  日期：1991.9

  Intramolecular free-radical reactions of allyloxy radicals to form tetrahydropyrans and cyclopentanols have been studied; the cyclopentanols form stereoselectivety with irons disposition of groups about the ring-forming bond.

  已经研究了烯丙氧基自由基形成四氢吡喃和环戊醇的分子内自由基反应。环戊醇形成立体选择性，铁在成环键周围的基团被铁取代。
• Rearrangement reactions of epoxides in the presence of 2-mercaptopyridine N-oxide sodium salt.
  作者：Christopher Lampard、John A. Murphy、Norman Lewis

  DOI：10.1016/s0040-4020(01)90235-2

  日期：1993.4

  Reaction of glycidyl bromides and tosylates with the sodium salt of mercaptopyridine N-oxide led to the formation of episulphides.

  缩水甘油基溴化物和甲苯磺酸盐与巯基吡啶N-氧化物的钠盐的反应导致表环硫化物的形成。
• 用于合成二硫代赤藓醇的中间化合物及其应 用和二硫代赤藓醇的合成方法
  申请人：新乡医学院

  公开号：CN111100096B

  公开（公告）日：2021-09-14

  本发明公开了一种用于合成二硫代赤藓醇的中间化合物及其应用和二硫代赤藓醇的合成方法，该中间化合物为2，3‑二乙酰基硫代甲基环氧乙烷，且该中间化合物的化学式为：其可通过将2，3‑二溴甲基环氧乙烷和硫代乙酸盐进行取代反应来制备。二硫代赤藓醇的合成方法包括：将该中间化合物进行水解反应。通过2，3‑二乙酰基硫代甲基环氧乙烷可直接水解得到二硫代赤藓醇，且2，3‑二乙酰基硫代甲基环氧乙烷的制备较简单，为二硫代赤藓醇的合成提供了一种新的合成思路，并且合成路线简短，操作简便，收率较高。
• Fluorodioxolane-containing alkynes [1,2]
  作者：Ming-H. Hung

  DOI：10.1016/s0022-1139(00)80132-3

  日期：1991.4

  Novel fluorinated dioxolane-containing alkyne compounds 1 and 2 were synthesized from hexafluoroacetone and either 1,4-dibromo-2-butene or propargyl alcohol.
• NOVEL AMIDE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1213281B1

  公开（公告）日：2004-02-18