1,3-dimethoxy-2-octylbenzene | 59968-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-dimethoxy-2-octylbenzene
• 英文别名: Benzene, 1,3-dimethoxy-2-octyl
• CAS: 59968-15-9
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: NJKIZYQPPYEBRG-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±22.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)
• 保留指数：
  1810

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-2-octylbenzene 在 双氧水 、 对甲苯磺酸 、 溶剂黄146 、 硝酸 作用下， 以 水 为溶剂， 反应 1.0h， 以32%的产率得到2-octyl-3-methoxycyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Synthesis of structurally simplified analogues of aplidinone A, a pro-apoptotic marine thiazinoquinone

  摘要：

  The synthesis of analogues of aplidinone A (7), a prenylated quinone isolated from the Mediterranean ascidian Aplidium conicum, has been performed. This work not only allowed confirming the structural assignment of aplidinone A, previously made with the support of GIAO shielding calculations, but, above all, made a series of structurally related quinone derivatives (compounds 8-13 and the natural metabolite) available for a screening in vitro for cytotoxic and pro-apoptotic activity and for SAR studies. The study evidenced one of the synthetic analogues (11) as a potent cytotoxic and pro-apoptotic agent against several tumor cell lines which also inhibits the TNF alpha-induced NF-kappa B activation in a human leukemia T cell line. This exemplifies the potential of a natural product to qualify as lead structure for medicinal chemistry campaigns, affording simplified analogues with better bioactivity and easier to synthesize. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.063
• 作为产物：
  描述：

  1-碘辛烷 、 间苯二甲醚 在 氯代异辛烷 、 sodium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以46%的产率得到1,3-dimethoxy-2-octylbenzene
  参考文献：
  名称：

  (2-乙基己基)钠：一种可溶于己烷的试剂，用于连续流中的 Br/Na 交换和定向金属化

  摘要：

  我们报告了在连续流动条件下使用钠填充床反应器从 3-(氯甲基)庚烷 ( 2 ) 按需生成可溶于己烷的 (2-乙基己基)钠 ( 1 )。因此，所得的1溶液不含元素钠，因此适合一系列合成应用。这种新程序避免了烷基钠的储存，并将金属钠的处理限制在最低限度。 (2-乙基己基)钠 ( 1 ) 被证明是一种非常有用的试剂，可以进行在线 Br/Na 交换以及定向钠化。随后将所得芳基钠中间体与各种亲电子试剂（例如酮、醛、Weinreb-酰胺、亚胺、烯丙基溴、二硫化物和烷基碘）分批捕获。还报道了使用在线亲电试剂猝灭的 Br/Na 交换反应放大。

  DOI：

  10.1002/anie.202103031

文献信息

• Process for intermediates to leukotriene antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0295882B1

  公开（公告）日：1991-08-21
• US4777299A
  申请人：——

  公开号：US4777299A

  公开（公告）日：1988-10-11
• (2‐Ethylhexyl)sodium: A Hexane‐Soluble Reagent for Br/Na‐Exchanges and Directed Metalations in Continuous Flow
  作者：Johannes H. Harenberg、Niels Weidmann、Alexander J. Wiegand、Carla A. Hoefer、Rajasekar Reddy Annapureddy、Paul Knochel

  DOI：10.1002/anie.202103031

  日期：2021.6.21

  hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be

  我们报告了在连续流动条件下使用钠填充床反应器从 3-(氯甲基)庚烷 ( 2 ) 按需生成可溶于己烷的 (2-乙基己基)钠 ( 1 )。因此，所得的1溶液不含元素钠，因此适合一系列合成应用。这种新程序避免了烷基钠的储存，并将金属钠的处理限制在最低限度。 (2-乙基己基)钠 ( 1 ) 被证明是一种非常有用的试剂，可以进行在线 Br/Na 交换以及定向钠化。随后将所得芳基钠中间体与各种亲电子试剂（例如酮、醛、Weinreb-酰胺、亚胺、烯丙基溴、二硫化物和烷基碘）分批捕获。还报道了使用在线亲电试剂猝灭的 Br/Na 交换反应放大。
• Synthesis of structurally simplified analogues of aplidinone A, a pro-apoptotic marine thiazinoquinone
  作者：Anna Aiello、Ernesto Fattorusso、Paolo Luciano、Marialuisa Menna、Marco A. Calzado、Eduardo Muñoz、Francesco Bonadies、Marcella Guiso、Maria Filomena Sanasi、Gianfranco Cocco、Rosario Nicoletti

  DOI：10.1016/j.bmc.2009.11.063

  日期：2010.1

  The synthesis of analogues of aplidinone A (7), a prenylated quinone isolated from the Mediterranean ascidian Aplidium conicum, has been performed. This work not only allowed confirming the structural assignment of aplidinone A, previously made with the support of GIAO shielding calculations, but, above all, made a series of structurally related quinone derivatives (compounds 8-13 and the natural metabolite) available for a screening in vitro for cytotoxic and pro-apoptotic activity and for SAR studies. The study evidenced one of the synthetic analogues (11) as a potent cytotoxic and pro-apoptotic agent against several tumor cell lines which also inhibits the TNF alpha-induced NF-kappa B activation in a human leukemia T cell line. This exemplifies the potential of a natural product to qualify as lead structure for medicinal chemistry campaigns, affording simplified analogues with better bioactivity and easier to synthesize. (C) 2009 Elsevier Ltd. All rights reserved.