[(1S)-1-[(2S)-2-methyloxiran-2-yl]-2-oxo-2-phenylmethoxyethyl] 5-methylnaphthalene-1-carboxylate | 783323-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(1S)-1-[(2S)-2-methyloxiran-2-yl]-2-oxo-2-phenylmethoxyethyl] 5-methylnaphthalene-1-carboxylate
• CAS: 783323-30-8
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: WQBJHRURWXHJCB-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[(2S)-2-methyloxiran-2-yl]-2-oxo-2-phenylmethoxyethyl] 5-methylnaphthalene-1-carboxylate 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-Methyl-naphthalene-1-carboxylic acid (S)-({ethoxycarbonyl-[(R)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-methyl}-carbamoyl)-((S)-2-methyl-oxiranyl)-methyl ester
  参考文献：
  名称：

  Delineating Noncovalent Interactions between the Azinomycins and Double-Stranded DNA:  Importance of the Naphthalene Substitution Pattern on Interstrand Cross-Linking Efficiency

  摘要：

  Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5' methyl group or both the C-5' methyl and C-3' methoxy groups are deleted from the naphthalene ring.

  DOI：

  10.1021/ol048653y
• 作为产物：
  描述：

  5-methyl-1-naphthoic acid 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 [(1S)-1-[(2S)-2-methyloxiran-2-yl]-2-oxo-2-phenylmethoxyethyl] 5-methylnaphthalene-1-carboxylate
  参考文献：
  名称：

  Delineating Noncovalent Interactions between the Azinomycins and Double-Stranded DNA:  Importance of the Naphthalene Substitution Pattern on Interstrand Cross-Linking Efficiency

  摘要：

  Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5' methyl group or both the C-5' methyl and C-3' methoxy groups are deleted from the naphthalene ring.

  DOI：

  10.1021/ol048653y

文献信息

• Delineating Noncovalent Interactions between the Azinomycins and Double-Stranded DNA:  Importance of the Naphthalene Substitution Pattern on Interstrand Cross-Linking Efficiency
  作者：Cyrille A. S. Landreau、Rachel C. LePla、Michael Shipman、Alexandra M. Z. Slawin、John A. Hartley

  DOI：10.1021/ol048653y

  日期：2004.9.1

  Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5' methyl group or both the C-5' methyl and C-3' methoxy groups are deleted from the naphthalene ring.