1-trimethylsilyl-3-(3,4-methylenedioxyphenyl)-1-propyne | 133218-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-trimethylsilyl-3-(3,4-methylenedioxyphenyl)-1-propyne
• 英文别名: [3-(1,3-benzodioxol-5-yl)-1-propynyl](trimethyl)silane；3-(1,3-benzodioxol-5-yl)prop-1-ynyl-trimethylsilane
• CAS: 133218-05-0
• 化学式: C₁₃H₁₆O₂Si
• 分子量: 232.354
• InChiKey: WWVULFDCMXRHHY-UHFFFAOYSA-N

物化性质

• 沸点：
  286.8±19.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-trimethylsilyl-3-(3,4-methylenedioxyphenyl)-1-propyne 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以92%的产率得到3-(3,4-methylenedioxyphenyl)-1-propyne
  参考文献：
  名称：

  Rossi, Renzo; Carpita, Adriano; Lippolis, Vito, Gazzetta Chimica Italiana, 1990, vol. 120, p. 783 - 791

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴甲基-苯并[1,3]二氧代 、 三甲基乙炔基硅 在 乙基溴化镁 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以90%的产率得到1-trimethylsilyl-3-(3,4-methylenedioxyphenyl)-1-propyne
  参考文献：
  名称：

  Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry

  摘要：

  Stesianacin and podophyllotoxin are two naturally occurring lignans first isolated from plant sources, which share the capability to disrupt tubulin assembly. Although not strictly essential for its activity, the lactone ring on both structures represents Achilles' heel, as it is a potential site of metabolic degradation and epimerization on its C2 carbon brings about a significant loss in potency. In the present manuscript, we have used the ruthenium-catalyzed [3+2] azide-alkyne cycloaddition, a click-chemistry reaction, to replace the lactone ring with a 1,5-disubstituted triazole in few synthetic steps. The compounds were cytotoxic, although to a lesser degree compared to podophyllotoxin, while retaining antitubulin activity. The present structures might therefore represent a good Platform for the fast generation of metabolically stable compounds with few stereogenic centers that might be of value from a medicinal chemistry point of view. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.020

文献信息

• ROSSI, RENZO;CARPITA, ADRIANO;LIPPOLIS, VITO;BENETTI, MASSIMO, GAZZ. CHIM. ITAL., 120,(1990) N2, C. 783-791
  作者：ROSSI, RENZO、CARPITA, ADRIANO、LIPPOLIS, VITO、BENETTI, MASSIMO

  DOI：——

  日期：——