tert-Butoxycarbonylamino-[(R)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester | 157825-42-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-Butoxycarbonylamino-[(R)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester
• 英文别名: ethyl (2E)-2-[(5R)-5-(hydroxymethyl)pyrrolidin-2-ylidene]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 157825-42-8
• 化学式: C₁₄H₂₄N₂O₅
• 分子量: 300.355
• InChiKey: OVBRSFDIGHQGDO-HNLKAFMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butoxycarbonylamino-[(R)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 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：

  benzyl (4R)-4-[(E)-5-ethoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3,5-dioxopent-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 tert-Butoxycarbonylamino-[(S)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 、 tert-Butoxycarbonylamino-[(R)-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 、 tert-Butoxycarbonylamino-[(S)-5-hydroxymethyl-pyrrolidin-(2Z)-ylidene]-acetic acid ethyl ester 、 ethyl (R)-2-(tert-butoxycarbonylamino)-2-(5-hydroxymethylpyrrolidin-2-ylidene)acetate
  参考文献：
  名称：

  A Synthetic Azinomycin Analogue with Demonstrated DNA Cross-Linking Activity: Insights into the Mechanism of Action of this Class of Antitumor Agent

  摘要：

  DOI：

  10.1002/1521-3773(20001002)39:19<3467::aid-anie3467>3.0.co;2-t

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.
• A Synthetic Azinomycin Analogue with Demonstrated DNA Cross-Linking Activity: Insights into the Mechanism of Action of this Class of Antitumor Agent
  作者：John A. Hartley、Ali Hazrati、Lloyd R. Kelland、Ruzwana Khanim、Michael Shipman、Franck Suzenet、Louise F. Walker

  DOI：10.1002/1521-3773(20001002)39:19<3467::aid-anie3467>3.0.co;2-t

  日期：2000.10.2