triethyl-(3-methyl-but-3-enyloxy)-silane | 80920-25-8

• 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: triethyl-(3-methyl-but-3-enyloxy)-silane
• 英文别名: triethyl-(3-methylbut-3-enyloxy)silane；2-methyl-4-(triethylsiloxy)-1-butene；Triethylsilyl 3-methylbut-3-ene ether；triethyl(3-methylbut-3-enoxy)silane
• CAS: 80920-25-8
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: ZFQWNXPEMHHERA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triethyl-(3-methyl-but-3-enyloxy)-silane 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 copper(I) bromide dimethylsulfide complex 、 D-(-)-酒石酸二乙酯 、 二氯乙基铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  BINOL-Ti-Catalyzed Carbonyl-Ene Cyclization by Tuning the 6-Br-Ligand for the Synthesis of 2-Methyl-19-nor-22-oxa Vitamin D Analogue with Significant Differentiation Activity

  摘要：

  通过调节 6-Br-BINOL 配体，在 BINOL-Ti 催化的不对称羰基烯环化过程中控制过渡态，完成了 2-甲基-19-去甲-22-氧杂 D3 类似物 A 环（2）的合成，该类似物在分化 HL-60 细胞方面具有显著活性。

  DOI：

  10.1055/s-1999-2989
• 作为产物：
  描述：

  3-甲基-3-丁烯-1-醇 、 三乙基硅烷 在 氢化钾 作用下， 生成 triethyl-(3-methyl-but-3-enyloxy)-silane
  参考文献：
  名称：

  Mironov, I. V.; Mel'nitskii, I. A.; Siraeva, I. N., Journal of general chemistry of the USSR, 1981, vol. 51, p. 2329 - 2332

  摘要：

  DOI：

文献信息

• Sustainable radical reduction through catalyzed hydrogen atom transfer reactions (CHAT-reactions)
  作者：Andreas Gansäuer、Matthias Otte、Frederik Piestert、Chun-An Fan

  DOI：10.1016/j.tet.2009.03.088

  日期：2009.6

  system with coupled catalytic cycles is described that allows radical reduction by catalyzed hydrogen atom transfer (CHAT) from transition metal hydrides. These intermediates are generated through H2 activation. Radical generation is carried out by titanocene catalyzed electron transfer to epoxides. The reaction provides a novel entry into the atom-economical reduction of radicals that has long been

  描述了具有耦合的催化循环的系统，其允许通过从过渡金属氢化物催化的氢原子转移（CHAT）进行自由基还原。这些中间体是通过H 2活化而产生的。自由基的产生是通过钛茂催化的电子转移到环氧化物上进行的。该反应为自由基的原子经济还原提供了新的途径，长期以来一直将其视为自由基化学工业应用的关键问题。
• Synthesis of Seven-Membered Cross-Conjugated Cyclic Trienes by 8π Electrocyclic Reaction
  作者：Ranmaru Kato、Hiroki Saito、Shoko Uda、Daisuke Domon、Kazutada Ikeuchi、Takahiro Suzuki、Keiji Tanino

  DOI：10.1021/acs.orglett.1c03383

  日期：2021.11.19

  A method for the synthesis of 3-methylene-1,4-cycloheptadiene derivatives via an 8π electrocyclization reaction was developed. The triene substrate bearing a phosphate or carbamate group was prepared from γ,δ-unsaturated esters and α,β-unsaturated aldehydes in four steps. Upon treatment with NaHMDS or KHMDS, the substrate formed a heptatrienyl anion, which underwent electrocyclization and subsequent

  开发了一种通过8π电环化反应合成3-亚甲基-1,4-环庚二烯衍生物的方法。由γ,δ-不饱和酯和α,β-不饱和醛分四步制备带有磷酸或氨基甲酸酯基团的三烯底物。在用 NaHMDS 或 KHMDS 处理后，底物形成了一个庚三烯基阴离子，它经历了电环化和随后的离去基团的 β-消除。该产物可以分两步转化为鎓盐。
• Synthesis of 1,2-Dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes
  作者：Armando Ramirez、K. A. Woerpel

  DOI：10.1021/ol051703u

  日期：2005.10.1

  The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.
• Hydroperoxidations of Alkenes using Cobalt Picolinate Catalysts
  作者：Zulema Peralta-Neel、K. A. Woerpel

  DOI：10.1021/acs.orglett.1c01489

  日期：2021.7.2
• Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum
  作者：Derek C. Martyn、Armando P. Ramirez、Meaghan J. Beattie、Joseph F. Cortese、Vishal Patel、Margaret A. Rush、K.A. Woerpel、Jon Clardy

  DOI：10.1016/j.bmcl.2008.10.083

  日期：2008.12

  Artemisinin-derived compounds play an integral role in current malaria chemotherapy. Given the virtual certainty of emerging resistance, we have investigated spiro-1,2-dioxolanes as an alternative scaffold. The endoperoxide functionality was generated by the SnCl(4)-mediated annulation of a bis-silylperoxide and an alkene. The first set of eight analogs gave EC(50) values of 50-150 nM against Plasmodium falciparum 3D7 and Dd2 strains, except for the carboxylic acid analog. A second series, synthesized by coupling a spiro-1,2-dioxolane carboxylic acid to four separate amines, afforded the most potent compound ( EC50 similar to 5 nM). (C) 2008 Elsevier Ltd. All rights reserved.