1-tert-butyl-1-siloxycyclopropane | 38858-75-2

• 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: 1-tert-butyl-1-siloxycyclopropane
• 英文别名: 1-Trimethylsilyloxy-1-t-butylcyclopropan；(1-tert-butyl-cyclopropoxy)-trimethyl-silane；1-tert-butyl-1-trimethylsilanyloxy-cyclopropane；(1-Tert-butylcyclopropyl)oxy-trimethylsilane
• CAS: 38858-75-2
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: LGSBHUMKLGPJKG-UHFFFAOYSA-N

物化性质

• 沸点：
  170.7±9.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-tert-butyl-1-siloxycyclopropane 在 copper(II) bis(tetrafluoroborate) 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以80%的产率得到2,2,9,9-tetramethyl-decane-3,8-dione
  参考文献：
  名称：

  Ryu, Ilhyong; Matsumoto, Koichi; Kameyama, Yasuhiro, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12330 - 12339

  摘要：

  DOI：
• 作为产物：
  描述：

  二碘甲烷 、 (1-叔丁基乙烯氧基)三甲基硅烷 在 铜 、 锌 作用下， 生成 1-tert-butyl-1-siloxycyclopropane
  参考文献：
  名称：

  Reaction of trimethysilyl enol ethers with Simmons-Smith reagent. Facile synthesis of trimethylsilyl cyclopropyl ethers and cyclopropanols

  摘要：

  DOI：

  10.1021/jo00951a032

文献信息

• Nitrene-promoted α-Alkoxylation of Amides with Silyl Ethers
  作者：Michiharu Mitani、Keiko Watanabe、Osamu Tachizawa、Kikuhiko Koyama

  DOI：10.1246/cl.1992.813

  日期：1992.5

  Thermolysis of a solution of amides, silyl ethers, and ethyl azidoformate caused the introduction of several alkoxy groups into the positions adjacent to the amide nitrogen.

  酰胺、甲硅烷基醚和叠氮甲酸乙酯溶液的热解导致在与酰胺氮相邻的位置引入几个烷氧基。
• Allylative ring opening of siloxycyclopropanes by silver fluoride and allylic chlorides affording δ, ε-unsaturated ketones
  作者：Ilhyong Ryu、Haruhisa Suzuki、Akiya Ogawa、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)82287-x

  日期：——

  Unconventional type of allylation reaction at the β-position of ketone carbonyl has been developed based on the β-metallo ketone strategy: treatment of siloxycyclopropanes 1 with allylic chlorides 2 in the presence of silver fluoride results in the effective formation of δ, ε-unsaturated ketones 4.

  基于β-金属酮的策略，已开发出在羰基酮的β位上的非常规类型的烯丙基化反应：在氟化银存在下，用烯丙基氯化物2处理甲硅烷氧基环丙烷1可以有效形成δ，ε-不饱和酮4。
• Synthesis of β-mercuri ketones by the reaction of siloxycyclopropanes with mercuric acetate and their conversion to α-methylene ketones and γ-ketoesters
  作者：Ilhyong Ryu、Koichi Matsumoto、Masato Ando、Shinji Murai、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)92884-3

  日期：1980.1

  Siloxycyclopropanes were quantitatively converted to β-acetoxymercuri ketones by the reaction with mercuric acetate. Successive treatment with palladium chloride or palladium chloride/carbon monoxide gave α-methylene ketones or γ-ketoesters, respectively, in good yields.

  通过与乙酸汞的反应，将甲硅烷氧基环丙烷定量地转化为β-乙酰氧基汞的酮。依次用氯化钯或氯化钯/一氧化碳进行处理，分别得到高收率的α-亚甲基酮或γ-酮酸酯。
• A new synthesis of β-bromo ketones by the reaction of silyl cyclopropyl ethers with bromine
  作者：Shinji Murai、Yoshio Seki、Noboru Sonoda

  DOI：10.1039/c39740001032

  日期：——

  A new synthesis of β-bromo ketones by the reaction of trimethylsilyl cyclopropyl ethers with bromine is described.

  描述了一种通过三甲基甲硅烷基环丙基醚与溴的反应合成β-溴酮的新方法。
• .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes
  作者：Hiroyuki Nakahira、Ilhyong Ryu、Masanobu Ikebe、Yoshiaki Oku、Akiya Ogawa、Nobuaki Kambe、Noboru Sonoda、Shinji Murai

  DOI：10.1021/jo00027a008

  日期：1992.1

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.