2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester | 157670-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester
• 英文别名: (Z)-methyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate；methyl (Z)-2-azido-3-(3,4-dimethoxyphenyl)acrylate；methyl (Z)-2-azido-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 157670-07-0
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: HSEXHHIJISLSJF-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 在 三溴化硼 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 4.25h， 生成 5,6-Dihydroxy-indol-2-carbonsaeure-methylester
  参考文献：
  名称：

  具有潜在抗病毒活性的超支化分子结构：5,6-二羟基吲哚-2-羧酸衍生物

  摘要：

  在寻找新的 HIV-1 整合酶 (IN) 抑制剂的过程中，我们合成了一系列多聚体 5,6-二羟基吲哚-2-羧酸 (DHICA) 衍生物。初步结果表明，超支化结构可能代表开发新的抗病毒先导化合物的特殊分子必需品。

  DOI：

  10.3390/11120968
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 3,4-二甲氧基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  具有潜在抗病毒活性的超支化分子结构：5,6-二羟基吲哚-2-羧酸衍生物

  摘要：

  在寻找新的 HIV-1 整合酶 (IN) 抑制剂的过程中，我们合成了一系列多聚体 5,6-二羟基吲哚-2-羧酸 (DHICA) 衍生物。初步结果表明，超支化结构可能代表开发新的抗病毒先导化合物的特殊分子必需品。

  DOI：

  10.3390/11120968

文献信息

• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。
• Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C−H Amination
  作者：Julien Bonnamour、Carsten Bolm

  DOI：10.1021/ol2004066

  日期：2011.4.15

  A practical iron-catalyzed intramolecular C−H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.

  提出了一种实用的铁催化分子内胺化反应及其在吲哚衍生物合成中的应用。作为催化剂，使用可商购的三氟甲磺酸铁（II）。
• Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks
  作者：Paul B. Huleatt、Sze Shiong Choo、Sheena Chua、Christina L.L. Chai

  DOI：10.1016/j.tetlet.2008.06.080

  日期：2008.9

  The synthesis of 3-, 4-, 7-bromo and 4,7-dibrominated 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives is reported. Hemetsberger and Bartoli indole syntheses were investigated and expedient routes to the desired compounds were developed. These indoles are valuable substrates for elaboration using transition metal-mediated cross-coupling chemistry. (C) 2008 Elsevier Ltd. All rights reserved.
• Effects of Indole Fatty Alcohols on the Differentiation of Neural Stem Cell Derived Neurospheres
  作者：Djalil Coowar、Julien Bouissac、Mazen Hanbali、Marie Paschaki、Eliane Mohier、Bang Luu

  DOI：10.1021/jm0493616

  日期：2004.12.1

  In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared. 13C (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.
• Intramolecular C−H Amination Reactions:  Exploitation of the Rh₂(II)-Catalyzed Decomposition of Azidoacrylates
  作者：Benjamin J. Stokes、Huijun Dong、Brooke E. Leslie、Ashley L. Pumphrey、Tom G. Driver

  DOI：10.1021/ja072219k

  日期：2007.6.1

  Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh-2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials.