1,2,3-trimethoxy-5-{[(prop-2-yn-1-yl)oxy]methyl}benzene

• 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: 1,2,3-trimethoxy-5-{[(prop-2-yn-1-yl)oxy]methyl}benzene
• 英文别名: 1,2,3-trimethoxy-5-((prop-2-yn-1-yloxy)methyl)benzene；1,2,3-trimethoxy-5-prop-2-ynyloxymethylbenzene；3,4,5-trimethoxybenzyl propargyl ether；3,4,5-trimethoxy-α-(2-propynyloxy)-toluene；1,2,3-Trimethoxy-5-(prop-2-ynoxymethyl)benzene
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: AEPOOQONPPYFBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3-trimethoxy-5-{[(prop-2-yn-1-yl)oxy]methyl}benzene 在 正丁基锂 、 四甲基乙二胺 、 水 、 mercury(II) trifluoroacetate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 2.05h， 生成 (+/-)-2-(1-allyl-1H-tetrazol-5-yl)-1-(3,4,5-trimethoxybenzyloxy)propan-2-ol
  参考文献：
  名称：

  5-羟烷基-1H-四唑的脱水裂解：生成亚烷基卡宾的温和途径

  摘要：

  据报道，开发了一种温和、无碱的亚烷基碳烯生成方法。用碳二亚胺处理 5-羟烷基-1 H -四唑会产生由推定的亚烷基碳烯的 1,2-重排或 [1,5]-C-H 键插入产生的产物。这种二价中间体的形成是通过四氮杂富烯的方式发生的，四氮杂富烯经历了 2 摩尔二氮的挤出。描述了该方法的细节、其在考布他汀 A-4 合成中的应用以及 5-羟烷基-1 H-四唑的改进路线。

  DOI：

  10.1021/ol300276p
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 甲醇 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 1,2,3-trimethoxy-5-{[(prop-2-yn-1-yl)oxy]methyl}benzene
  参考文献：
  名称：

  Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization

  摘要：

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.063

文献信息

• Propynyl benzyl ethers
  申请人：Hoffmann-La Roche Inc.

  公开号：US03946040A1

  公开（公告）日：1976-03-23

  Propynyl benzyl ethers having juvenile hormone-like activity which are 4-halogen, lower alkyl, lower alkoxy or propynyloxy substituted or 3,4-lower alkylenedioxy substituted and which can also be 3,5- and/or .alpha.-substituted, and insecticide compositions that include at least one propynyl benzyl ether and that can also include a conventional insect-poison.

  具有类似于幼虫激素活性的丙炔基苄醚，其为4-卤素、较低烷基、较低烷氧基或丙炔氧基取代或3,4-较低烷基二氧取代的化合物，也可以是3,5-和/或α-取代的化合物，以及包括至少一种丙炔基苄醚的杀虫剂组合物，该组合物还可以包括传统的杀虫剂。
• Efficient synthetic methods for unsaturated 3,4,5-trimethoxybenzyl sulfides and ethers
  作者：V. A. Potapov、V. A. Panov、M. V. Musalov、S. A. Zhivet’eva、M. V. Musalova、A. G. Khabibulina、S. V. Amosova

  DOI：10.1134/s107042801611004x

  日期：2016.11

  Convenient and efficient procedures were developed for preparation of 3,4,5-trimethoxybenzyl sulfides and ethers containing vinyl, allyl, and propargyl groups proceeding from 3,4,5-trimethoxybenzyl alcohol, elemental sulfur, and thiourea in basic and basic-reductive systems (hydrazine hydrate‒KОН‒DMF, NaBH4‒EtOH, KОН‒DMSO). The effective method of the synthesis of 1,1'-[disulfandiylbis(methylene)]bis-(3,4,

  为在碱性和碱性还原体系中从3,4,5-三甲氧基苄醇，元素硫和硫脲制备3,4,5-三甲氧基苄基硫化物和含乙烯基，烯丙基和炔丙基的醚开发了一种便捷有效的方法（水合肼‒KОН‒DMF，NaBH 4 ‒EtOH，KОНОDMSO）。合成1,1'-[二硫杂双基双（亚甲基）]双-（3,4,5-三甲氧基苯）的有效方法是在水合肼存在下，用水合肼将元素硫还原为二硫阴离子在相转移催化条件下或在DMF中与3,4,5-三甲氧基苄基氯反应。
• US3946040A
  申请人：——

  公开号：US3946040A

  公开（公告）日：1976-03-23
• Dehydrative Fragmentation of 5-Hydroxyalkyl-1<i>H</i>-tetrazoles: A Mild Route to Alkylidenecarbenes
  作者：Duncan J. Wardrop、John P. Komenda

  DOI：10.1021/ol300276p

  日期：2012.3.16

  The development of a mild, base-free method for the generation of alkylidenecarbenes is reported. Treatment of 5-hydroxyalkyl-1H-tetrazoles with carbodiimides generates products arising from the 1,2-rearrangement or [1,5]-C–H bond insertion of a putative alkylidenecarbene. Formation of this divalent intermediate is proposed to occur by way of a tetraazafulvene, which undergoes extrusion of 2 mol of

  据报道，开发了一种温和、无碱的亚烷基碳烯生成方法。用碳二亚胺处理 5-羟烷基-1 H -四唑会产生由推定的亚烷基碳烯的 1,2-重排或 [1,5]-C-H 键插入产生的产物。这种二价中间体的形成是通过四氮杂富烯的方式发生的，四氮杂富烯经历了 2 摩尔二氮的挤出。描述了该方法的细节、其在考布他汀 A-4 合成中的应用以及 5-羟烷基-1 H-四唑的改进路线。
• Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization
  作者：P. Suman、T. Ramalinga Murthy、K. Rajkumar、D. Srikanth、Ch. Dayakar、Chandan Kishor、Anthony Addlagatta、Shasi V. Kalivendi、B. China Raju

  DOI：10.1016/j.ejmech.2014.11.063

  日期：2015.1

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.