2-acetoxy-6-formylbenzyl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-acetoxy-6-formylbenzyl acetate
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: HURKWROSWMTALL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-acetoxy-6-formylbenzyl acetate 在 吡啶 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 氢氟酸 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 12.83h， 生成 3',4'-O-isopropylidenepyriculol
  参考文献：
  名称：

  A unified approach to the salicylaldehyde containing polyketide natural products: Total synthesis of ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, sordariol, sordarial, 12-methoxy sordariol, and agropyrenol

  摘要：

  Many fungal metabolites are salicylaldehyde containing polyketide natural products and are often isolated from the fungus culture broth. These metabolites commonly exhibit phytotoxicity, however, some compounds exerted other biological activities including immunosuppressive activity. We have developed a unified synthetic strategy that provides easy access to ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, trans-sordariol, trans-sordarial, 12-methoxy sordariol and agropyrenol. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131368
• 作为产物：
  描述：

  二甲酚 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 36.17h， 生成 2-acetoxy-6-formylbenzyl acetate
  参考文献：
  名称：

  A unified approach to the salicylaldehyde containing polyketide natural products: Total synthesis of ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, sordariol, sordarial, 12-methoxy sordariol, and agropyrenol

  摘要：

  Many fungal metabolites are salicylaldehyde containing polyketide natural products and are often isolated from the fungus culture broth. These metabolites commonly exhibit phytotoxicity, however, some compounds exerted other biological activities including immunosuppressive activity. We have developed a unified synthetic strategy that provides easy access to ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, trans-sordariol, trans-sordarial, 12-methoxy sordariol and agropyrenol. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131368

文献信息

• A unified approach to the salicylaldehyde containing polyketide natural products: Total synthesis of ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, sordariol, sordarial, 12-methoxy sordariol, and agropyrenol
  作者：Gaddam Mahesh、Jakka Raghavaiah、Gangarajula Sudhakar

  DOI：10.1016/j.tet.2020.131368

  日期：2020.7

  Many fungal metabolites are salicylaldehyde containing polyketide natural products and are often isolated from the fungus culture broth. These metabolites commonly exhibit phytotoxicity, however, some compounds exerted other biological activities including immunosuppressive activity. We have developed a unified synthetic strategy that provides easy access to ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, trans-sordariol, trans-sordarial, 12-methoxy sordariol and agropyrenol. (C) 2020 Elsevier Ltd. All rights reserved.