1-((2-(chloromethyl)allyl)oxy)-4-methoxybenzene | 90855-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-((2-(chloromethyl)allyl)oxy)-4-methoxybenzene
• 英文别名: 3-chloro-2-(4-methoxyphenoxymethyl)propene；1-[2-(Chloromethyl)prop-2-enoxy]-4-methoxybenzene
• CAS: 90855-63-3
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: XMLVJZAIQDNGCB-UHFFFAOYSA-N

物化性质

• 沸点：
  323.7±27.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-((2-(chloromethyl)allyl)oxy)-4-methoxybenzene 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到2-(4-methoxyphenoxymethyl)-2-propenylamine
  参考文献：
  名称：

  Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid

  摘要：

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.

  DOI：

  10.1021/jo802791r
• 作为产物：
  描述：

  methanesulfonic acid 2-chloromethyl-allyl ester 、 4-甲氧基苯酚 在 sodium hydride 作用下， 生成 1-((2-(chloromethyl)allyl)oxy)-4-methoxybenzene
  参考文献：
  名称：

  Discovery and SAR of para-alkylthiophenoxyacetic acids as potent and selective PPARδ agonists

  摘要：

  Synthesis and SAR of para-alkylthiophenoxyacetic acids is described. Achiral compounds 30, 31 and 32 were identified as potent and selective PPARd agonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.113

文献信息

• Design, synthesis and anti-tumor efficacy evaluation of novel 1,3-diaryl propane-based polyphenols obtained from Claisen rearrangement reaction
  作者：Song-Wei Jiang、Xiang Qi、Haowen Deng、Yuan Gao、Yinghui Yuan、Xiawen Dang、Bing Xu、Shitang Ma、Tian Xie、Xiang-Yang Ye、Zi Hui

  DOI：10.1016/j.bioorg.2023.106753

  日期：2023.11

  synthetic compounds with interesting biological activities. Inspired by their structural feature, a total of 49 1,3-diaryl propane-based polyphenols were designed and synthesized through Claisen rearrangement reaction. New compounds were initially assessed for their anti-proliferative activities against various cancer cell lines (PC-3, U87MG, U251, HCT116) at a concentration of 50 μM, and the results

  白藜芦醇、和厚朴酚、去甲二氢愈创木酸等多酚广泛存在于天然产物或具有有趣生物活性的合成化合物中。受其结构特征的启发，通过克莱森重排反应设计并合成了总共49种1,3-二芳基丙烷基多酚。初步评估了新化合物在 50 μM 浓度下对各种癌细胞系（PC-3、U87MG、U251、HCT116）的抗增殖活性，结果指导了该系列化合物的 SAR。针对七种癌细胞系（选择了另外三种结肠癌细胞系，即 COLO205、HT29 和 SW480）进一步筛选选定的化合物，鉴定出两种先进的先导化合物 2t 和 3t，其 IC 50 值范围为 8.2 ± 0.1至19.3 ± 1.9微米。两种化合物还以剂量和时间依赖性方式显示出针对 COLO205 的有前景的抗增殖活性。此外，2t和3t在COLO205异种移植小鼠模型中表现出良好的抗肿瘤功效，TGI值在38%至58%之间。这些结果值得对这一系列化合物进行进一步研究。
• Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid
  作者：Eva Van Hende、Guido Verniest、Frederik Deroose、Jan-Willem Thuring、Gregor Macdonald、Norbert De Kimpe

  DOI：10.1021/jo802791r

  日期：2009.3.6

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.
• Discovery and SAR of para-alkylthiophenoxyacetic acids as potent and selective PPARδ agonists
  作者：Rui Zhang、Alan DeAngelis、Aihua Wang、Ellen Sieber-McMaster、Xun Li、Ronald Russell、Patricia Pelton、Jun Xu、Peifang Zhu、Lubing Zhou、Keith Demarest、William V. Murray、Gee-Hong Kuo

  DOI：10.1016/j.bmcl.2008.12.113

  日期：2009.2

  Synthesis and SAR of para-alkylthiophenoxyacetic acids is described. Achiral compounds 30, 31 and 32 were identified as potent and selective PPARd agonists. (C) 2009 Elsevier Ltd. All rights reserved.