6-methoxy-7-acetoxy-1-tetralone | 71089-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-7-acetoxy-1-tetralone
• 英文别名: 7-Acetoxy-6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalin；7-acetoxy-6-methoxytetralin-1-one；(3-methoxy-8-oxo-6,7-dihydro-5H-naphthalen-2-yl) acetate
• CAS: 71089-44-6
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: VSNCKEPHGBMKNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-acetoxy-1-tetralone 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以98%的产率得到6-methoxy-7-hydroxy-1-tetralone
  参考文献：
  名称：

  Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes

  摘要：

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.

  DOI：

  10.1021/jo981950u
• 作为产物：
  描述：

  6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以62%的产率得到6-methoxy-7-acetoxy-1-tetralone
  参考文献：
  名称：

  Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes

  摘要：

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.

  DOI：

  10.1021/jo981950u

文献信息

• Formation and composition of new optically active compounds
  申请人：The Research Foundation of State University of New York

  公开号：US06284789B1

  公开（公告）日：2001-09-04

  The present invention is directed to tetrahydronaphthalene derivatives of &agr;-conindendrin, &bgr;-conindendrin, sikkimotoxin, and podophyllotoxin having at least one methyleneoxy bridge wherein the oxygen atom extends to the benzhydrylic carbon atom.

  本发明涉及至少具有一个亚甲氧基桥的α-孔雀菜碱、β-孔雀菜碱、西木毒素和鬼臼毒素的四氢萘衍生物，其中氧原子延伸到苯丙基碳原子。
• US6284789B1
  申请人：——

  公开号：US6284789B1

  公开（公告）日：2001-09-04
• Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes
  作者：Frank D. Ramdayal、David J. Kiemle、Robert T. LaLonde

  DOI：10.1021/jo981950u

  日期：1999.6.1

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.