5,7,8-trimethoxy-6-(3-methylbut-2-enyl)naphthalen-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,7,8-trimethoxy-6-(3-methylbut-2-enyl)naphthalen-1-ol
• 英文别名: 5,7,8-Trimethoxy-6-(3-methylbut-2-enyl)naphthalen-1-ol
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: MEPKUQKLCIMXET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7,8-trimethoxy-6-(3-methylbut-2-enyl)naphthalen-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 6-(3,3-dimethyl-oxiranylmethyl)-5,7,8-trimethoxynaphthalen-1-yl acetate
  参考文献：
  名称：

  Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization

  摘要：

  The first total synthesis of (+/-)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (+/-)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyallcyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (+/-)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.081
• 作为产物：
  描述：

  1-溴-2,4,5-三甲氧基苯 在 正丁基锂 、 高氯酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 22.92h， 生成 5,7,8-trimethoxy-6-(3-methylbut-2-enyl)naphthalen-1-ol
  参考文献：
  名称：

  Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization

  摘要：

  The first total synthesis of (+/-)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (+/-)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyallcyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (+/-)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.081

文献信息

• Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization
  作者：Tokutaro Ogata、Yoshiko Sugiyama、Saki Ito、Kazuha Nakano、Eri Torii、Arisa Nishiuchi、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2013.09.081

  日期：2013.12

  The first total synthesis of (+/-)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (+/-)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyallcyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (+/-)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively. (C) 2013 Elsevier Ltd. All rights reserved.