Dechlorodihydromaldoxin

• 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: Dechlorodihydromaldoxin
• 英文别名: 2-hydroxy-6-(2-hydroxy-4-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoic acid
• 化学式: C₁₇H₁₆O₈
• 分子量: 348.309
• InChiKey: SOXXAFVUSIMAGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Dechlorodihydromaldoxin 在 碘苯二乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 1.0h， 以7.5 mg的产率得到methyl 5-hydroxy-4'-methoxy-7-methyl-4,6'-dioxospiro[4H-1,3-benzodioxine-2,1'-cyclohexa-2',4'-diene]-2'-carboxylate
  参考文献：
  名称：

  Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

  摘要：

  An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.

  DOI：

  10.1021/ol201561w
• 作为产物：
  描述：

  2,4-dihydroxy-6-[(phenylmethoxy)methyl]-benzaldehyde 在 sodium chlorite 、 正丁基锂 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 20 % Pd(OH)2/C 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 28.33h， 生成 Dechlorodihydromaldoxin
  参考文献：
  名称：

  Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

  摘要：

  An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.

  DOI：

  10.1021/ol201561w

文献信息

• Polyketide Production of Pestaloficiols and Macrodiolide Ficiolides Revealed by Manipulations of Epigenetic Regulators in an Endophytic Fungus
  作者：Guangwei Wu、Haichuan Zhou、Peng Zhang、Xiuna Wang、Wei Li、Weiwei Zhang、Xingzhong Liu、Hong-Wei Liu、Nancy P. Keller、Zhiqiang An、Wen-Bing Yin

  DOI：10.1021/acs.orglett.6b00562

  日期：2016.4.15

  Regarding targeted disruption of epigenetic regulators, histone methyltransferase and deacetylase in a plant endophytic fungus Pestalotiopsis fici have been uncovered as an unexplored chemical repertoire. Manipulation of epigenetic regulators led to the isolation of 15 new polyketides, including pestaloficiols T-W (1-3 and 5), as well as 11 macrodiolide ficiolides A-K (6-16). Ficiolide K (16) was found to contain a very rare 1,6-anhydro-pyranose moiety. Finally, the biosynthetic origin of macrodiolide was characterized by isotope-labeling experiments.
• Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin
  作者：Min Yu、Barry B. Snider

  DOI：10.1021/ol201561w

  日期：2011.8.19

  An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.