(Z)-2-tert-Butoxycarbonylamino-3-(6,7-dimethoxy-2-oxo-2H-chromen-4-yl)-acrylic acid methyl ester | 805251-82-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (Z)-2-tert-Butoxycarbonylamino-3-(6,7-dimethoxy-2-oxo-2H-chromen-4-yl)-acrylic acid methyl ester
• 英文别名: methyl (Z)-3-(6,7-dimethoxy-2-oxochromen-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]prop-2-enoate
• CAS: 805251-82-5
• 化学式: C₂₀H₂₃NO₈
• 分子量: 405.405
• InChiKey: IFYJVPGJSDSYJL-QPEQYQDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-2-tert-Butoxycarbonylamino-3-(6,7-dimethoxy-2-oxo-2H-chromen-4-yl)-acrylic acid methyl ester 在 {(1,5-cyclooctadiene)Rh(1,2-bis((2R,5R)-2,5-diethylphospholano)benzene)}triflate 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到(S)-2-tert-Butoxycarbonylamino-3-(6,7-dimethoxy-2-oxo-2H-chromen-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  An efficient synthesis of the intrinsic fluorescent peptide labels, (S)- and (R)-(6,7-dimethoxy-4-coumaryl)alanines via asymmetric hydrogenations

  摘要：

  The title compounds 1a,b are efficiently synthesized in high yields and with high enantioselectivity (>95% ee) by using a sequence in which the key step involves asymmetric hydrogenation of dehydroamino methyl ester 4 with Burk's DuPHOS-based Rh(I) catalysts. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.093
• 作为产物：
  描述：

  6,7-二甲氧基-4-甲基香豆素 在 selenium(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 5.0h， 生成 (Z)-2-tert-Butoxycarbonylamino-3-(6,7-dimethoxy-2-oxo-2H-chromen-4-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  An efficient synthesis of the intrinsic fluorescent peptide labels, (S)- and (R)-(6,7-dimethoxy-4-coumaryl)alanines via asymmetric hydrogenations

  摘要：

  The title compounds 1a,b are efficiently synthesized in high yields and with high enantioselectivity (>95% ee) by using a sequence in which the key step involves asymmetric hydrogenation of dehydroamino methyl ester 4 with Burk's DuPHOS-based Rh(I) catalysts. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.093

文献信息

• An efficient synthesis of the intrinsic fluorescent peptide labels, (S)- and (R)-(6,7-dimethoxy-4-coumaryl)alanines via asymmetric hydrogenations
  作者：Wei Wang、Hao Li

  DOI：10.1016/j.tetlet.2004.09.093

  日期：2004.11

  The title compounds 1a,b are efficiently synthesized in high yields and with high enantioselectivity (>95% ee) by using a sequence in which the key step involves asymmetric hydrogenation of dehydroamino methyl ester 4 with Burk's DuPHOS-based Rh(I) catalysts. (C) 2004 Elsevier Ltd. All rights reserved.