2-(2-甲氧基-5-甲基苯基)苯甲醛 | 1255635-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-甲氧基-5-甲基苯基)苯甲醛
• 英文名称: 2-(2-methoxy-5-methylphenyl)benzaldehyde
• CAS: 1255635-28-9
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: FLUKDSYZYFGTOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-甲氧基-5-甲基苯基)苯甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate 、 三溴化硼 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 2-methyl-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain

  摘要：

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.

  DOI：

  10.1021/np4005882
• 作为产物：
  描述：

  2-甲氧基-5-甲基苯硼酸 、 邻溴苯甲醛 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醚 、 水 、 甲苯 为溶剂， 生成 2-(2-甲氧基-5-甲基苯基)苯甲醛
  参考文献：
  名称：

  手性布朗斯台德酸催化炔基硫醚的不对称脱芳香螺环化

  摘要：

  炔烃的区域选择性转化代表了有机合成中高效的成键策略。然而，炔烃转化中的对映体控制仍然具有挑战性，特别是对于无金属方法。在此，我们描述了通过苯酚的脱芳构化进行的手性布朗斯台德酸催化的炔基硫醚的对映选择性螺环化。这种无金属方案可实现手性螺[4.5]癸-6-酮的绿色、原子经济制备，收率良好至优异，具有高对映选择性。重要的是，该方案代表了炔基硫醚不对称转化的第一个无金属例子。

  DOI：

  10.1039/d3gc03222a

文献信息

• The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain
  作者：Antonio Jacinto Demuner、Luiz Cláudio Almeida Barbosa、Ana Cristina Mendes Miranda、Guilherme Carvalho Geraldo、Cleiton Moreira da Silva、Samuele Giberti、Michele Bertazzini、Giuseppe Forlani

  DOI：10.1021/np4005882

  日期：2013.12.27

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.
• Chiral Brønsted acid-catalyzed asymmetric dearomative spirocyclization of alkynyl thioethers
  作者：Xin-Yang Fan、Jia-Cheng Li、Ji-Jia Zhou、Bo Zhou、Long-Wu Ye

  DOI：10.1039/d3gc03222a

  日期：——

  bond-forming strategy in organic synthesis. However, the enantiocontrol in the conversion of alkynes remains challenging, especially for the metal-free approach. Herein, we describe a chiral Brønsted acid-catalyzed enantioselective spirocyclization of alkynyl thioethers via dearomatization of phenols. This metal-free protocol leads to the green and atom-economical preparation of chiral spiro[4.5]decan-6-ones

  炔烃的区域选择性转化代表了有机合成中高效的成键策略。然而，炔烃转化中的对映体控制仍然具有挑战性，特别是对于无金属方法。在此，我们描述了通过苯酚的脱芳构化进行的手性布朗斯台德酸催化的炔基硫醚的对映选择性螺环化。这种无金属方案可实现手性螺[4.5]癸-6-酮的绿色、原子经济制备，收率良好至优异，具有高对映选择性。重要的是，该方案代表了炔基硫醚不对称转化的第一个无金属例子。