methyl 5-hydroxy-4'-methoxy-7-methyl-4,6'-dioxospiro[4H-1,3-benzodioxine-2,1'-cyclohexa-2',4'-diene]-2'-carboxylate | 1320259-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 5-hydroxy-4'-methoxy-7-methyl-4,6'-dioxospiro[4H-1,3-benzodioxine-2,1'-cyclohexa-2',4'-diene]-2'-carboxylate
• 英文别名: dechloromaldoxin；Methyl 5-hydroxy-3'-methoxy-7-methyl-4,5'-dioxospiro[1,3-benzodioxine-2,6'-cyclohexa-1,3-diene]-1'-carboxylate；methyl 5-hydroxy-3'-methoxy-7-methyl-4,5'-dioxospiro[1,3-benzodioxine-2,6'-cyclohexa-1,3-diene]-1'-carboxylate
• CAS: 1320259-43-5
• 化学式: C₁₇H₁₄O₈
• 分子量: 346.293
• InChiKey: YHXYUFVUDCUDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3-甲基丁-1,3-二烯-1-亚基)环己烷 、 methyl 5-hydroxy-4'-methoxy-7-methyl-4,6'-dioxospiro[4H-1,3-benzodioxine-2,1'-cyclohexa-2',4'-diene]-2'-carboxylate 以 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 以23%的产率得到
  参考文献：
  名称：

  Diels–Alder reaction of maldoxin with an isopropenylallene

  摘要：

  The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 degrees C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild conditions, whereas the analogous Diels-Alder adduct from the dimethoxycyclohexadienone did not undergo an ene reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.117
• 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 、 碘苯二乙酸 、 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 、 2,2,2-三氟乙醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 29.33h， 生成 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

文献信息

• Diels–Alder reaction of maldoxin with an isopropenylallene
  作者：Min Yu、Barry B. Snider

  DOI：10.1016/j.tet.2011.09.117

  日期：2011.12

  The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 degrees C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild conditions, whereas the analogous Diels-Alder adduct from the dimethoxycyclohexadienone did not undergo an ene reaction. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.