6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene | 17212-96-3

• 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-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 7-Acetoxy-6-methoxy-1,2,3,4-tetrahydronaphthalene；6-acetoxy-7-methoxytetralin；(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl) acetate
• CAS: 17212-96-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: ZIFHCRGVXSGPMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 碳酸氢钠 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成 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：

  2-Naphthalenecarbonyl chloride, 5,6,7,8-tetrahydro-3-methoxy- 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, and pyrogallol annulation. Regiospecific total synthesis of sendaverine and a preparation of 6,7-benzomorphans

  摘要：

  DOI：

  10.1021/jo00195a033

文献信息

• Inverse electron demand diels-alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, pyrogallol annulation.
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1016/s0040-4039(01)99816-8

  日期：1983.1

  m-CPBA] allows the preparation of a full range of oxygen substituted aromatics from a single intermediate and represent methods of benzene, 1-, 2- or 3-phenol, symmetrical or unsymmetrical catechol, resorcinol and pyrogallol annulation.

  3-碳甲氧基-2-吡喃酮与N-乙烯基-2-吡咯烷酮，碳酸亚乙烯酯，1,1-二甲氧基乙烯或1,1,2-三甲氧基乙烯的四个逆电子需求Diels-Alder反应之一的实现，然后选择两个标准反应顺序：（1）除去甲氧羰基（NaOH；铜粉，喹啉，Δ）或（2）将其转化为乙酸盐[NaOH：（CO）2 Cl 2：（CH 3）2 CuLi：m- CPBA]允许从单一中间体制备全范围的氧取代的芳族化合物，并代表苯，1-，2-或3-苯酚，对称或不对称的邻苯二酚，间苯二酚和邻苯三酚环化的方法。
• 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桥的α-孔雀酸、β-孔雀酸、锡木毒素和植物鬼臼毒素的四氢萘衍生物，其中氧原子延伸至苯甲基碳原子。
• BOGER, D. L.;MULLICAN, M. D., TETRAHEDRON LETT., 1983, 24, N 45, 4939-4942
  作者：BOGER, D. L.、MULLICAN, M. D.

  DOI：——

  日期：——
• US6284789B1
  申请人：——

  公开号：US6284789B1

  公开（公告）日：2001-09-04
• Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, and pyrogallol annulation. Regiospecific total synthesis of sendaverine and a preparation of 6,7-benzomorphans
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1021/jo00195a033

  日期：1984.10