2,4,5-trimethoxyphenylacetylene | 101911-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4,5-trimethoxyphenylacetylene
• 英文别名: 1-ethynyl-2,4,5-trimethoxybenzene
• CAS: 101911-62-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: ZKYMLCRGRSTAGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,4,5-trimethoxyphenylacetylene 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙酸乙酯 为溶剂， 20.0~145.0 ℃ 、344.75 kPa 条件下， 反应 17.0h， 生成 3,5-diacetoxy-1-[2-(2,4,5-trimethoxyphenyl)ethyl]benzene
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054
• 作为产物：
  描述：

  1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.5h， 以97%的产率得到2,4,5-trimethoxyphenylacetylene
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054

文献信息

• 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance
  作者：Aleem Gangjee、Ojas A. Namjoshi、Staci N. Keller、Charles D. Smith

  DOI：10.1016/j.bmc.2011.05.030

  日期：2011.7

  clinically used antimitotic agents. This report consists of an attempt to optimize the various activities of the parent compounds by synthetic variations of the phenyl ring of the 5-phenylethyl side chain. The target compounds were synthesized via a nine-step synthesis involving a Sonogashira reaction. The substituted phenylacetylenes as coupling partners were in turn synthesized from unactivated aryl

  Gangjee 等人 最近报道了一系列新的2-氨基-4-甲基-5-苯乙基取代-7-苄基-吡​​咯并[2,3- d]嘧啶，其中一些表现出两位数纳摩尔的抗肿瘤和抗有丝分裂活性，并且不受 P-糖蛋白 (Pgp) 或多药耐药蛋白 1 (MRP1) 介导的肿瘤耐药性的影响（与长春花生物碱和紫杉烷不同）。这些化合物中的一些，除了它们的抗肿瘤活性外，还能够逆转 Pgp 介导的对临床使用的抗有丝分裂剂的抗性。本报告试图通过 5-苯乙基侧链的苯环的合成变化来优化母体化合物的各种活性。目标化合物是通过涉及 Sonogashira 反应的九步合成合成的。作为偶联伙伴的取代苯乙炔依次由未活化的芳基溴化物或碘化物合成。目标化合物对 MCF-7 肿瘤细胞表现出中等的细胞毒性。然而，这些化合物中的大多数对抗性 NCI/ADR 和 MCF-7/VP 显示出改善的细胞毒性。该研究提供了一种类似物，可以逆转 Pgp 介导的以及
• Catalytic C–C Cleavage/Alkyne–Carbonyl Metathesis Sequence of Cyclobutanones
  作者：Jiqiang Gao、Chunhui Liu、Zhongjuan Li、Haotian Liang、Yuhui Ao、Jinbo Zhao、Yuchao Wang、Yuanqi Wu、Yu Liu

  DOI：10.1021/acs.orglett.0c01317

  日期：2020.5.15

  substrates decorated with various substituents at different positions were all well accommodated. Preliminary mechanistic studies show that silver salt acted as a Lewis acid to facilitate both C-C cleavage of the cyclobutanone moiety and the subsequent metathesis between C═O and C≡C bonds.

  首次实现了由AgSbF6催化的炔烃系环丁酮的开环/炔烃羰基复分解序列，以在温和条件下提供多取代的萘​​基酮。很好地容纳了在不同位置装饰有各种取代基的一系列基材。初步的机理研究表明，银盐起路易斯酸的作用，既促进了环丁酮部分的CC裂解，又促进了C═O和C≡C键之间的易位。
• Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer
  作者：Shankar Thangaraj、Wen-Shing Tsao、Yi-Wei Luo、Yean-Jang Lee、Chia-Fu Chang、Chun-Cheng Lin、Biing-Jiun Uang、Chia-Chun Yu、Jih-Hwa Guh、Che-Ming Teng

  DOI：10.1016/j.tet.2011.06.054

  日期：2011.8

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.