1-Boc-2-chloroindole-3-carboxylic acid | 721443-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Boc-2-chloroindole-3-carboxylic acid
• 英文别名: 1-t-Boc-2-chloroindole-3-carboxylic acid；1-(tert-butoxycarbonyl)-2-chloro-1H-indole-3-carboxylic acid；2-chloro-1-[(2-methylpropan-2-yl)oxycarbonyl]indole-3-carboxylic acid
• CAS: 721443-57-8
• 化学式: C₁₄H₁₄ClNO₄
• 分子量: 295.722
• InChiKey: QGARXLIAXAOOLO-UHFFFAOYSA-N

物化性质

• 沸点：
  451.0±48.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Boc-2-chloroindole-3-carboxylic acid 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 methyl 1-Boc-2-chloroindole-3-carboxamide
  参考文献：
  名称：

  Phytoalexins from the Crucifer Rutabaga:  Structures, Syntheses, Biosyntheses, and Antifungal Activity

  摘要：

  Phytoalexins are inducible chemical defenses produced de novo by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from economically important crucifers lead us to examine rutabaga tubers (Brassica napus L. ssp. rapifera). Three new phytoalexins, named isalexin (9), brassicanate A (10), and rutalexin (11), were isolated together with five known phytoalexins, brassinin (4), 1-methoxybrassinin (5), spirobrassinin (13), brassicanal A (14), and brassilexin (15). The chemical structures of the new phytoalexins were proven by syntheses, and their biological activity against four plant pathogens were determined. Biosynthetic studies using tetra- and pentadeuterated precursors established that indolyl-3-acetaldoxime (22) and brassinin (4) are precursors of brassicanate A (10) and rutalexin (11) and that cyclobrassinin (23) is a biosynthetic precursor of rutalexin (11), whereas tryptamine (24) is not a precursor of rutabaga phytoalexins.

  DOI：

  10.1021/jo049648a
• 作为产物：
  描述：

  1-Boc-2-氯-3-甲酰基吲哚 在 sodium chlorite 、 potassium dihydrogenphosphate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以96%的产率得到1-Boc-2-chloroindole-3-carboxylic acid
  参考文献：
  名称：

  Phytoalexins from the Crucifer Rutabaga:  Structures, Syntheses, Biosyntheses, and Antifungal Activity

  摘要：

  Phytoalexins are inducible chemical defenses produced de novo by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from economically important crucifers lead us to examine rutabaga tubers (Brassica napus L. ssp. rapifera). Three new phytoalexins, named isalexin (9), brassicanate A (10), and rutalexin (11), were isolated together with five known phytoalexins, brassinin (4), 1-methoxybrassinin (5), spirobrassinin (13), brassicanal A (14), and brassilexin (15). The chemical structures of the new phytoalexins were proven by syntheses, and their biological activity against four plant pathogens were determined. Biosynthetic studies using tetra- and pentadeuterated precursors established that indolyl-3-acetaldoxime (22) and brassinin (4) are precursors of brassicanate A (10) and rutalexin (11) and that cyclobrassinin (23) is a biosynthetic precursor of rutalexin (11), whereas tryptamine (24) is not a precursor of rutabaga phytoalexins.

  DOI：

  10.1021/jo049648a

文献信息

• Phytoalexins from the Crucifer Rutabaga:  Structures, Syntheses, Biosyntheses, and Antifungal Activity
  作者：M. Soledade C. Pedras、Sabine Montaut、Mojmir Suchy

  DOI：10.1021/jo049648a

  日期：2004.6.1

  Phytoalexins are inducible chemical defenses produced de novo by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from economically important crucifers lead us to examine rutabaga tubers (Brassica napus L. ssp. rapifera). Three new phytoalexins, named isalexin (9), brassicanate A (10), and rutalexin (11), were isolated together with five known phytoalexins, brassinin (4), 1-methoxybrassinin (5), spirobrassinin (13), brassicanal A (14), and brassilexin (15). The chemical structures of the new phytoalexins were proven by syntheses, and their biological activity against four plant pathogens were determined. Biosynthetic studies using tetra- and pentadeuterated precursors established that indolyl-3-acetaldoxime (22) and brassinin (4) are precursors of brassicanate A (10) and rutalexin (11) and that cyclobrassinin (23) is a biosynthetic precursor of rutalexin (11), whereas tryptamine (24) is not a precursor of rutabaga phytoalexins.
• Biotransformation of rutabaga phytoalexins by the fungus Alternaria brassicicola: Unveiling the first hybrid metabolite derived from a phytoalexin and a fungal polyketide
  作者：M. Soledade C. Pedras、Abbas Abdoli

  DOI：10.1016/j.bmc.2016.11.017

  日期：2017.1

  The biotransformations of the rutabaga phytoalexins rutalexin, brassicanate A, isalexin and rapalexin A by the plant pathogenic fungus Alternaria brassicicola are reported. While the biotransformations of rutalexin, brassicanate A, and isalexin are fast, rapalexin A is resistant to fungal transformation. Unexpectedly, biotransformation of rutalexin yields a hybrid metabolite named rutapyrone, derived from rutalexin metabolism and phomapyrone G, a fungal metabolite produced by A. brassicicola. These fungal transformations are detoxification reactions likely carried out by different enzymes. The discovery of rapalexin A resistance to detoxification suggests that this phytoalexin in combination with additional phytoalexins could protect crucifers against this pathogen. Phytoalexins resistant to degradation by A. brassicicola are expected to provide the producing plants with higher disease resistance levels. (C) 2016 Elsevier Ltd. All rights reserved.