2,3,5-Trimethoxy-7-methyl-1-(propan-2-yl)naphthalene | 89043-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,5-Trimethoxy-7-methyl-1-(propan-2-yl)naphthalene
• 英文别名: 2,3,5-trimethoxy-7-methyl-1-propan-2-ylnaphthalene
• CAS: 89043-02-7
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: GVJYEELSKPAYFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,5-Trimethoxy-7-methyl-1-(propan-2-yl)naphthalene 、 N-甲基甲酰苯胺 在 叔丁基锂 作用下， 以 环己烷 为溶剂， 反应 26.0h， 以49%的产率得到4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde
  参考文献：
  名称：

  Synthesis of hemigossypol and its derivatives

  摘要：

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.089
• 作为产物：
  描述：

  2,3-二甲氧基-1,4-苯醌 在 三乙基硅烷 、 N-溴代丁二酰亚胺(NBS) 、 potassium phosphate monohydrate 、 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 palladium 10% on activated carbon 、 rel-(2R,3R)-2-[双(1,1-二甲基乙基)次膦基]-3-(1,1-二甲基乙基)-2,3-二氢-N,N-二甲基-1,3-氧杂磷杂戊环-4-胺 、 氢气 、 三溴化磷 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -78.0~100.0 ℃ 、689.49 kPa 条件下， 反应 35.5h， 生成 2,3,5-Trimethoxy-7-methyl-1-(propan-2-yl)naphthalene
  参考文献：
  名称：

  铃木-Miyaura交叉偶联有效合成带有无环仲烷基的立体受阻芳烃

  摘要：

  庞大的P，P = O配体设计用于在位阻芳基卤化物和烷基硼酸之间的交叉偶联过程中抑制异构化和还原副反应。高产率地实现了二邻位取代的芳基溴化物和无环仲烷基硼酸之间的Suzuki-Miyaura交叉偶联。该方法还能够以优异的收率制备带有异丙基的邻烷氧基双邻取代芳烃。合成方法的实用性已在雌酮的后期修饰中以及在向棉酚的新合成途径中的应用中得到了证明。

  DOI：

  10.1002/anie.201411518

文献信息

• Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids
  作者：Tengda Si、Bowen Li、Wenrui Xiong、Bin Xu、Wenjun Tang

  DOI：10.1039/c7ob02531a

  日期：——

  Aryl–secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,PO ligand L1/L2 is

  芳基-仲烷基与芳基磺酸酯作为偶联伙伴的交叉偶联仍然是一个巨大的挑战。首次实现了芳基/烯基三氟甲磺酸酯与无环仲烷基硼酸之间的有效交叉偶联，从而以良好或优异的收率提供了一系列空间上拥挤的无环仲烷基芳烃/烯烃。使用空间庞大的P，P O配体L1 / L2对于高收率和选择性至关重要。该方法实现了男性避孕药和PAF拮抗剂棉酚的关键中间体的简明和4步合成。
• Efficient Synthesis of Sterically Hindered Arenes Bearing Acyclic Secondary Alkyl Groups by Suzuki-Miyaura Cross-Couplings
  作者：Chengxi Li、Tianyu Chen、Bowen Li、Guolan Xiao、Wenjun Tang

  DOI：10.1002/anie.201411518

  日期：2015.3.16

  Bulky P,PO ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki–Miyaura cross‐couplings between di‐ortho‐substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho‐alkoxy di‐ortho‐substituted

  庞大的P，P = O配体设计用于在位阻芳基卤化物和烷基硼酸之间的交叉偶联过程中抑制异构化和还原副反应。高产率地实现了二邻位取代的芳基溴化物和无环仲烷基硼酸之间的Suzuki-Miyaura交叉偶联。该方法还能够以优异的收率制备带有异丙基的邻烷氧基双邻取代芳烃。合成方法的实用性已在雌酮的后期修饰中以及在向棉酚的新合成途径中的应用中得到了证明。
• Synthesis of hemigossypol and its derivatives
  作者：Jun Wei、David L. Vander Jagt、Robert E. Royer、Lorraine M. Deck

  DOI：10.1016/j.tetlet.2010.08.089

  日期：2010.11

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.