adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester methyl ester | 457612-25-8

• 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: adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester methyl ester
• 英文别名: 6-O-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-O-methyl hexanedioate
• CAS: 457612-25-8
• 化学式: C₁₆H₂₁NO₈
• 分子量: 355.345
• InChiKey: PEDKNASXHZLFBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  471.3±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester methyl ester 以 乙醇 、 正己烷 、 乙腈 、 苯 为溶剂， 反应 25.0h， 生成 己二酸二甲酯
  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 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 正己烷 、 氯仿 、 苯 为溶剂， 反应 27.0h， 生成 adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester methyl 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

文献信息

• Clean and Easy Photochemistry
  作者：Claire-Lise Ciana、Christian G. Bochet

  DOI：10.2533/chimia.2007.650

  日期：——

  In this paper we try to convince you that the usual prejudices against photochemistry are not always well founded, supported by examples from the literature and from our own work. In fact, photochemistry can be a very powerful tool, for example in some elegant total syntheses which use key photochemical steps. Furthermore, the exploitation of chromatic orthogonality which allows wavelength-selective reactions, and recent strategies opening the possibility of enantioselective catalysis in photochemical reactions, expand the scope of this versatile synthetic tool. Finally, state-of-art LED-technology has allowed the development of small and easy-to-use photoreactors.

  在这篇论文中，我们试图通过文献和我们自己的工作的例子来证明，对于光化学的通常偏见并不总是有根据的。事实上，光化学可以是一个非常强大的工具，例如在一些优雅的全合成中使用关键的光化学步骤。此外，利用色差正交性，实现波长选择性反应的开发，以及最近的策略开辟了光化学反应中对映选择性催化的可能性，扩展了这种多功能合成工具的范围。最后，最先进的LED技术使得小型和易于使用的光反应器的开发成为可能。
• Wavelength-Controlled Orthogonal Photolysis of Protecting Groups
  作者：Aurélien Blanc、Christian G. Bochet

  DOI：10.1021/jo025837m

  日期：2002.8.1

  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.