2-methoxycarbonyloxycinnamic acid | 252258-20-1

• 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-methoxycarbonyloxycinnamic acid
• 英文别名: 2-methoxycarbonyloxy-trans-cinnamic acid；2-Methoxycarbonyloxy-trans-zimtsaeure；Carbomethoxycumarsaeure；(E)-3-(2-methoxycarbonyloxyphenyl)prop-2-enoic acid
• CAS: 252258-20-1
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: XBCCAXQALICZRU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-methoxycarbonyloxycinnamic acid 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 25.5h， 生成 butane 1,4-di-(2-methoxycarbonyloxy)cinnamate
  参考文献：
  名称：

  Effect of Substitution on the 2+2 Cycloaddition Reaction of Phenylpropanoids

  摘要：

  Formation of the cyclobutane products truxillic and truxinic acid within the plant cell wall could occur by photocycloaddition or possibly by enzyme-mediated radical coupling. Model precursors were synthesized and the mode of formation of the cyclobutane products was investigated. Modeling studies suggested that all the model compounds with the exception of the 2-hydroxylated diester contained the correct geometry for photocyclization and this was confirmed by irradiation. Delocalization of the unpaired electron was measured by ESR and the photochemical reaction rates were compared with the partial atomic orbital population of the singly occupied molecular orbital. It was observed that the 3-hydroxylated derivative had almost no delocalization to C8 and the lowest reaction rate. The rate of reaction increased with increasing extent of methoxylation. Incubation with silver oxide or with peroxidase failed to induce intramolecular dimerization. These results suggest that the biological mode of formation of truxillic and truxinic acid is the most likely via light-catalyzed 2+2 cycloaddition. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1143
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 、 氯甲酸甲酯 在 sodium hydroxide 作用下， 反应 4.0h， 以68%的产率得到2-methoxycarbonyloxycinnamic acid
  参考文献：
  名称：

  Effect of Substitution on the 2+2 Cycloaddition Reaction of Phenylpropanoids

  摘要：

  Formation of the cyclobutane products truxillic and truxinic acid within the plant cell wall could occur by photocycloaddition or possibly by enzyme-mediated radical coupling. Model precursors were synthesized and the mode of formation of the cyclobutane products was investigated. Modeling studies suggested that all the model compounds with the exception of the 2-hydroxylated diester contained the correct geometry for photocyclization and this was confirmed by irradiation. Delocalization of the unpaired electron was measured by ESR and the photochemical reaction rates were compared with the partial atomic orbital population of the singly occupied molecular orbital. It was observed that the 3-hydroxylated derivative had almost no delocalization to C8 and the lowest reaction rate. The rate of reaction increased with increasing extent of methoxylation. Incubation with silver oxide or with peroxidase failed to induce intramolecular dimerization. These results suggest that the biological mode of formation of truxillic and truxinic acid is the most likely via light-catalyzed 2+2 cycloaddition. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1143

文献信息

• Verticillium wilt of potato: a model of key factors related to disease severity and tuber yield in Southeastern Idaho
  作者：J. R. Davis、O. C. Huisman、D. O. Everson、A. T. Schneider

  DOI：10.1007/bf02875694

  日期：2001.7

  In three years (1994, 1995, and 1996), a total of 100 commercial potato fields in southeastern Idaho were surveyed for soil variables, severity of Verticillium wilt, soil inoculum density of Verticillium dahliae and Colletotrichum coccodes, colonization of stems, root, and tubers by V. dahliae and C. coccodes, and tuber yield, size, and quality. As a generalization, factors related to soil integrity (organic matter, organic nitrogen, and increased nutrient availability) were most closely related to wilt suppression and higher tuber yields, whereas factors related to loss of soil integrity (sodium and reduced nutrient availability) were related to increased wilt and lower tuber yields. In a multiple regression analysis, three independent variables, feeder-root infections by V. dahliae, sodium content in soil, and soil organic content, were significant predictors of tuber yield. With these three factors, this model accounted for 49%, 53%, and 62% of the field variability related to total yield in 1994, 1995, and 1996, respectively. Throughout this investigation, V. dahliae root infections had the most direct effect on tuber yield, which emphasizes the importance of quantifying root infections in epidemiological studies of Verticillium wilt. Based on these results, organic matter may be one factor that can be manipulated for suppression of Verticillium wilt without reducing soil populations of the pathogen.
• Effect of Substitution on the 2+2 Cycloaddition Reaction of Phenylpropanoids
  作者：Wendy R. Russell、A.Bryan Hanley、Mark J. Burkitt、Andrew Chesson

  DOI：10.1006/bioo.1999.1143

  日期：1999.10

  Formation of the cyclobutane products truxillic and truxinic acid within the plant cell wall could occur by photocycloaddition or possibly by enzyme-mediated radical coupling. Model precursors were synthesized and the mode of formation of the cyclobutane products was investigated. Modeling studies suggested that all the model compounds with the exception of the 2-hydroxylated diester contained the correct geometry for photocyclization and this was confirmed by irradiation. Delocalization of the unpaired electron was measured by ESR and the photochemical reaction rates were compared with the partial atomic orbital population of the singly occupied molecular orbital. It was observed that the 3-hydroxylated derivative had almost no delocalization to C8 and the lowest reaction rate. The rate of reaction increased with increasing extent of methoxylation. Incubation with silver oxide or with peroxidase failed to induce intramolecular dimerization. These results suggest that the biological mode of formation of truxillic and truxinic acid is the most likely via light-catalyzed 2+2 cycloaddition. (C) 1999 Academic Press.