(1-Isopropyl-cyclopropoxy)-trimethyl-silane | 101653-02-5

• 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-Isopropyl-cyclopropoxy)-trimethyl-silane
• 英文别名: Trimethyl{[1-(propan-2-yl)cyclopropyl]oxy}silane；trimethyl-(1-propan-2-ylcyclopropyl)oxysilane
• CAS: 101653-02-5
• 化学式: C₉H₂₀OSi
• 分子量: 172.343
• InChiKey: RPHBQFBQSSDUDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  153.6±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)：
  3.03
• 重原子数：
  11
• 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-Isopropyl-cyclopropoxy)-trimethyl-silane 在 四甲基乙二胺 、 四氯化锡 作用下， 生成 4-甲基-1-戊烯-3-酮
  参考文献：
  名称：

  .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes

  摘要：

  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.

  DOI：

  10.1021/jo00027a008
• 作为产物：
  描述：

  三甲基氯硅烷 、 1-(丙-2-基)环丙-1-醇 在 吡啶 作用下， 反应 2.0h， 生成 (1-Isopropyl-cyclopropoxy)-trimethyl-silane
  参考文献：
  名称：

  A facile cyclopropanol synthesis from β-halo ester with grignard reagent-samarium(II) diiodide couple

  摘要：

  Transformation of alpha,beta-halo ester to the cyclopropanols by a coupled reagent of samarium(II) diiodide with Grignard reagent in tetrahydrofuran-hexamethylphosphoric triamide was very successfully under mild conditions.

  DOI：

  10.1016/0040-4039(91)80567-p

文献信息

• β-Carbonyl radicals as three-carbon building blocks for carbon-carbon bond forming reactions
  作者：Bernd Giese、Hans Horler

  DOI：10.1016/s0040-4020(01)97181-9

  日期：1985.1

  aldehydes, ketones and esters β-carbonyl radicals can be generated via enolization, cyclopropanation, solvomercuration and reduction with NaBH4. Radicals react with electron-poor alkenes to give products of CC-bond forming reactions (Tables 1–3). Carbonyl compounds are therefore precursors of three-carbon building blocks. The products result from reactions with “Umpolung”.

  通过醛化，环丙烷化，溶剂化和NaBH 4还原，可以从醛，酮和酯生成β-羰基自由基。自由基与贫电子烯烃反应生成CC键形成反应的产物（表1-3）。因此，羰基化合物是三碳构件的前体。产物来自与“ Umpolung”的反应。
• 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。
• Ryu, Ilhyong; Matsumoto, Koichi; Kameyama, Yasuhiro, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12330 - 12339
  作者：Ryu, Ilhyong、Matsumoto, Koichi、Kameyama, Yasuhiro、Ando, Masato、Kusumoto, Nobuo、Ogawa, Akiya、Kambe, Nobuaki、Murai, Shinji、Sonoda, Noboru

  DOI：——

  日期：——
• RYU, I.;MURAI, S.;SONODA, N., J. ORG. CHEM., 1986, 51, N 12, 2389-2391
  作者：RYU, I.、MURAI, S.、SONODA, N.

  DOI：——

  日期：——
• RYU, ILHYONG;SUZUKI, HARUHISA;OGAWA, AKIYA;KAMBE, NOBUAKI;SONODA, NOBORU, TETRAHEDRON LETT., 29,(1988) N 47, C. 6137-6140
  作者：RYU, ILHYONG、SUZUKI, HARUHISA、OGAWA, AKIYA、KAMBE, NOBUAKI、SONODA, NOBORU

  DOI：——

  日期：——