(4-[1,3]Dioxolan-2-yl-phenyl)-trimethyl-silane | 180143-70-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4-[1,3]Dioxolan-2-yl-phenyl)-trimethyl-silane
• 英文别名: [4-(1,3-Dioxolan-2-yl)phenyl]-trimethylsilane
• CAS: 180143-70-8
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: JAZQMRAIHVDWHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (4-[1,3]Dioxolan-2-yl-phenyl)-trimethyl-silane 在 乙酸铵 、 lithium aluminium tetrahydride 作用下， 生成 (+/-)-2-Amino-1-(4-trimethylsilyl-phenyl)-propan
  参考文献：
  名称：

  Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors

  摘要：

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.

  DOI：

  10.1002/ps.2780440406
• 作为产物：
  描述：

  对溴苯甲醛 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 16.5h， 生成 (4-[1,3]Dioxolan-2-yl-phenyl)-trimethyl-silane
  参考文献：
  名称：

  亲电 N-亚硝基糖精试剂催化有机硅烷原硝化

  摘要：

  将N-硝基糖精试剂与路易斯酸活化相结合，可以实现（杂）芳基硅烷的轻松、区域选择性和化学选择性硝化，从而可以在前所未有的温和条件下引入硝基，适合复杂和多官能化分子的后期硝化。理论和实验机制研究制定了涉及“惠兰过渡态”的合理机制。

  DOI：

  10.1002/anie.202310851

文献信息

• Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors
  作者：Mary L. Arnold、Albert D. Duriatti、Michel Jung、Ruth B. Katz、John W. Liebeschuetz

  DOI：10.1002/ps.2780440406

  日期：1995.8

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.
• Catalytic <i>ipso</i>‐Nitration of Organosilanes Enabled by Electrophilic <i>N</i>‐Nitrosaccharin Reagent
  作者：Ivan Mosiagin、Anthony J. Fernandes、Alena Budinská、Liana Hayriyan、Kai E. O. Ylijoki、Dmitry Katayev

  DOI：10.1002/anie.202310851

  日期：2023.10.9

  Deploying N-nitrosaccharin reagents in combination with Lewis acid activation enables the facile, regio- and chemoselective nitration of (het)aryl silanes, allowing the introduction of nitro group under unprecedently mild conditions suitable for the late-stage nitration of complex and polyfunctionalized molecules. Theoretical and experimental mechanistic investigations formulate a plausible mechanism

  将N-硝基糖精试剂与路易斯酸活化相结合，可以实现（杂）芳基硅烷的轻松、区域选择性和化学选择性硝化，从而可以在前所未有的温和条件下引入硝基，适合复杂和多官能化分子的后期硝化。理论和实验机制研究制定了涉及“惠兰过渡态”的合理机制。