2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester | 574735-09-4

• 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: 2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester
• CAS: 574735-09-4
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: HHBUIHNQNVUWGQ-ZDUSSCGKSA-N

物化性质

• 沸点：
  489.3±45.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester 在 lithium hydroxide 、 二苯基二硒醚 、 水 、 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-(3-羟基-4-甲氧基苯基)-L-丙氨酸
  参考文献：
  名称：

  Synthesis of tyrosine derivatives for saframycin MX1 biosynthetic studies

  摘要：

  Saframycin MX1 and structural relatives are natural anticancer agents isolated from bacteria and marine invertebrates. For biosynthetic studies and to make a library of modified natural products, a series of tyrosine derivatives were synthesized in a concise manner. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.112
• 作为产物：
  描述：

  N-[(1,1-dimethylethoxy)carbonyl]-3-(3-formyl-4-hydroxyphenyl)-L-alanine 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以86%的产率得到2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of tyrosine derivatives for saframycin MX1 biosynthetic studies

  摘要：

  Saframycin MX1 and structural relatives are natural anticancer agents isolated from bacteria and marine invertebrates. For biosynthetic studies and to make a library of modified natural products, a series of tyrosine derivatives were synthesized in a concise manner. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.112

文献信息

• A general approach to l-tyrosine porphyrins
  作者：Hong Chen、Xue-Bin Shao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/s0040-4020(03)00487-3

  日期：2003.5

  A novel and general approach has been developed to prepare L-tyrosine-containing porphyrins. The key intermediates, 2-tert-butoxycarbonylamino-3-(3-formyl-4-hexyloxy-phenyl)-propionic acid bexyl ester and 2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester, were prepared by the Reimer-Tiemann reaction of Boc-protected L-tyrosine, which was followed by esterification and alkylation of the phenol hydroxide. A number of novel chiral L-tyrosine porphyrins were obtained from the reactions of 2-tert-butoxycarbonylamino-3-(3-formyl-4-alkoxy-phenyl)-propionic acid ester with different dipyrrolylmethanes and the reaction of 5-(4-trifluoromethylphenyl)pyrromethane afforded the highest yield. The tyrosine porphyrins could be readily deprotected to afford the corresponding diacid or diamine derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.