oxalic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester | 457612-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: oxalic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester
• 英文别名: 2-[(4,5-Dimethoxy-2-nitrophenyl)methoxy]-2-oxoacetic acid
• CAS: 457612-02-1
• 化学式: C₁₁H₁₁NO₈
• 分子量: 285.21
• InChiKey: DCHKXNYSBYPTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxybenzoin 、 oxalic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以36%的产率得到oxalic acid (4,5-dimethoxy-2-nitrobenzyl) ester (3',5'-dimethoxybenzoin) ester
  参考文献：
  名称：

  Wavelength-Controlled Orthogonal Photolysis of Protecting Groups

  摘要：

  The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3',5'-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.

  DOI：

  10.1021/jo025837m
• 作为产物：
  描述：

  6-硝基藜芦醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 oxalic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester
  参考文献：
  名称：

  Wavelength-Controlled Orthogonal Photolysis of Protecting Groups

  摘要：

  The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3',5'-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.

  DOI：

  10.1021/jo025837m