2-bromomethyl-3-phenyloxirane | 155728-88-4

• 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: 2-bromomethyl-3-phenyloxirane
• 英文别名: 2-[bromo(phenyl)methyl]oxirane
• CAS: 155728-88-4
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: BUKROXWCJIXKMO-UHFFFAOYSA-N

物化性质

• 沸点：
  260.1±20.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-bromomethyl-3-phenyloxirane 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以50%的产率得到3-苯基丙-2-烯-1-醇
  参考文献：
  名称：

  Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

  摘要：

  A combination of sodium borohydride and a catalytic amount of indium(Ill) chloride in acetonitrile reduces 2,3-epoxy-bromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C-O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.120
• 作为产物：
  描述：

  (1-bromoallyl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-bromomethyl-3-phenyloxirane
  参考文献：
  名称：

  Ganesh; Krupadanam, G.L. David, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 1, p. 34 - 38

  摘要：

  DOI：

文献信息

• A Novel Synthesis of 2-Hydroxymethyl-3-Phenyl-1, 4-Benzodioxanes
  作者：T. Ganesh、G. L. David Krupadanam

  DOI：10.1080/00397919808004893

  日期：1998.8

  The reaction of 3,4-dihydroxybenzaldehyde (4a), methyl-(3,4-dihydroxy) benzoate (4b), ethyl-(3,4-dihydroxy) benzoate (4c), 3,4-dihydroxybenzonitrile (4d), 2,3-dihydroxynitrobenzene (4e) with 2-bromomethyl-3-phenyl oxirane (3) in acetone-K2CO3 medium gave six membered heterocycles, 2-hydroxymethyl-3-phenyl-1,4-benzodioxanes (5a-e) regioselectively.
• A New Synthesis of 4-Phenylquinolines by Reaction of 2-(a-Bromobenzyl)oxiranes with Aniline Derivatives
  作者：Michinori Karikomi、Hiroshi Tsukada、Takashi Toda

  DOI：10.3987/com-01-9234

  日期：——

  Several 4-phenylquinoline derivatives were synthesized by reaction of (2R*,1 'R*)-2-(alpha -bromobenzyl)oxiranes (1a) with aniline derivatives, and the following treatment of the formed 3-hydroxy-4-phenyl-1,2,3,4-tetrahydroquinolines (2) with the Rydon reagent, and potassium t-butoxide and air oxidation.
• Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system
  作者：Brindaban C. Ranu、Subhash Banerjee、Arijit Das

  DOI：10.1016/j.tetlet.2004.09.120

  日期：2004.11

  A combination of sodium borohydride and a catalytic amount of indium(Ill) chloride in acetonitrile reduces 2,3-epoxy-bromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C-O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction. (C) 2004 Elsevier Ltd. All rights reserved.
• Ganesh; Krupadanam, G.L. David, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 1, p. 34 - 38
  作者：Ganesh、Krupadanam, G.L. David

  DOI：——

  日期：——