4(R),5(S)-benzopyrene-4,5-epoxide | 72010-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4(R),5(S)-benzopyrene-4,5-epoxide
• 英文别名: (17R,19S)-18-oxahexacyclo[10.7.2.03,8.09,20.016,21.017,19]henicosa-1,3,5,7,9(20),10,12(21),13,15-nonaene
• CAS: 72010-12-9
• 化学式: C₂₀H₁₂O
• 分子量: 268.315
• InChiKey: XGZQLNASOQVQTD-UXHICEINSA-N

物化性质

• 沸点：
  518.9±19.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

SDS

反应信息

• 作为反应物：
  描述：

  4(R),5(S)-benzopyrene-4,5-epoxide 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 43.83h， 生成 trans-4-(acetyloxy)-4,5-dihydro-5-benzopyrenamine
  参考文献：
  名称：

  On the regioselectivity in transformation of benzo[a]pyrene 4,5-oxide and 3-methylcholanthrene 11,12-oxide to the corresponding β-amino-alcohol d

  摘要：

  beta-Amino-alcohol derivatives of benzo[a]pyrene and 3-methylcholanthrene, 8, 9 and 15 which are assumed to take part in the transformation of the K-region oxides 1 and 10 to the corresponding arene imines, have been prepared. The sequence of reactions consists of nucleophilic oxirane ring opening of the epoxides by azide ion, acetylation of the separated isomeric trans-azido alcohols so formed, and palladium catalyzed hydrogenation of the resulting beta-acetyloxy azides under ambient conditions. The ratios between the isomeric azido-hydrins obtained from 1 and 10, as well as the product distribution in azide-induced oxirane ring cleavage in other carbocyclic and heterocyclic arene oxides have been shown to correlate with Huckel-type calculations of Wheland's pi-localization energies.

  DOI：

  10.1016/s0040-4020(01)85570-8
• 作为产物：
  描述：

  cis-4,5-dihydroxy-4,5-dihydrobenzo[a]pyrene 、 原乙酸三甲酯 、 三甲基氯硅烷 、 sodium methylate 生成 4(R),5(S)-benzopyrene-4,5-epoxide
  参考文献：
  名称：

  BALANI S.; BLADEREN P.; CASSIDY E.; BOYD D.; JERINA D., J. ORG. CHEM., 52,(1987) N 1, 137-144

  摘要：

  DOI：

文献信息

• Synthesis of glutathione adducts of K-region arene oxides
  作者：Oscar Hernandez、Madathil B. Gopinathan

  DOI：10.1039/c39840001491

  日期：——

  The K-region oxides of phenanthrene, pyrene, and benzo[a]pyrene react with N-trifuoroacetylglutathione dimethyl ester to give diastereoisomeric conjugates amenable to separation by chromatography.

  菲，pyr和苯并[ a ] K的K区氧化物与N-三氟乙酰乙酰谷胱甘肽二甲酯反应，得到适合通过色谱分离的非对映异构体共轭物。
• Absolute configurations of K-region epoxide enantiomers of 3-methylcholanthrene, benz[a]anthracene, and benzo[a]pyrene
  作者：Henri B. Weems、Mohammad. Mushtaq、Shen K. Yang

  DOI：10.1021/ac00149a011

  日期：1987.11.15
• WEEMS, HENRI B.;MUSHTAQ, MOHAMMAD;YANG, CHEN K., ANAL. CHEM., 59,(1987) N 22, 2679-2688
  作者：WEEMS, HENRI B.、MUSHTAQ, MOHAMMAD、YANG, CHEN K.

  DOI：——

  日期：——
• BALANI S.; BLADEREN P.; CASSIDY E.; BOYD D.; JERINA D., J. ORG. CHEM., 52,(1987) N 1, 137-144
  作者：BALANI S.、 BLADEREN P.、 CASSIDY E.、 BOYD D.、 JERINA D.

  DOI：——

  日期：——
• On the regioselectivity in transformation of benzo[a]pyrene 4,5-oxide and 3-methylcholanthrene 11,12-oxide to the corresponding β-amino-alcohol d
  作者：Jochanan Blum、Merav Setty-Fichman、Lea Efron、Sason Shaik、Ronald G. Harvey

  DOI：10.1016/s0040-4020(01)85570-8

  日期：1994.1

  beta-Amino-alcohol derivatives of benzo[a]pyrene and 3-methylcholanthrene, 8, 9 and 15 which are assumed to take part in the transformation of the K-region oxides 1 and 10 to the corresponding arene imines, have been prepared. The sequence of reactions consists of nucleophilic oxirane ring opening of the epoxides by azide ion, acetylation of the separated isomeric trans-azido alcohols so formed, and palladium catalyzed hydrogenation of the resulting beta-acetyloxy azides under ambient conditions. The ratios between the isomeric azido-hydrins obtained from 1 and 10, as well as the product distribution in azide-induced oxirane ring cleavage in other carbocyclic and heterocyclic arene oxides have been shown to correlate with Huckel-type calculations of Wheland's pi-localization energies.