(9CI)-(1,1-二甲基乙基)[(1-乙氧基环丙基)氧基]二甲基-硅烷 | 117726-73-5

• 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
• 中文名称: (9CI)-(1,1-二甲基乙基)[(1-乙氧基环丙基)氧基]二甲基-硅烷
• 英文名称: 1-Ethoxy-1-(tert-butyldimethylsiloxy)cyclopropan
• 英文别名: Silane, (1,1-dimethylethyl)[(1-ethoxycyclopropyl)oxy]dimethyl-(9CI)；tert-butyl-(1-ethoxycyclopropyl)oxy-dimethylsilane
• CAS: 117726-73-5
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: NHLLTCZAWPDZSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  一氧化碳 、 (9CI)-(1,1-二甲基乙基)[(1-乙氧基环丙基)氧基]二甲基-硅烷 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 氯仿 为溶剂， 60.0 ℃ 、101.32 kPa 条件下， 以59%的产率得到4-氧代庚二酸二乙酯
  参考文献：
  名称：

  Synthesis of 1,4-dicarbonyl compounds and 4-keto pimelates by palladium-catalyzed carbonylation of siloxycyclopropanes

  摘要：

  Palladium-catalyzed reaction of a siloxycyclopropane with an aryl triflate under carbon monoxide pressure (10-20 atm) in HMPA and that with carbon monoxide in chloroform provides new synthetic routes to 1,4-dicarbonyl compounds and 4-keto pimelates, respectively. The reaction of a siloxycyclopropane with a vinyl triflate, on the other hand, gives an acyloxycyclopropane instead.

  DOI：

  10.1016/s0040-4020(01)86434-6
• 作为产物：
  描述：

  β-(Iodzinkio)propionsaeureethylester 、 叔丁基二甲基氯硅烷 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成 (9CI)-(1,1-二甲基乙基)[(1-乙氧基环丙基)氧基]二甲基-硅烷
  参考文献：
  名称：

  Tamaru, Yoshinao; Tanigawa, Hiroto; Yamamoto, Tetsuji, Angewandte Chemie, 1989, vol. 101, # 3, p. 358 - 360

  摘要：

  DOI：

文献信息

• Palladium- and platinum-catalyzed reaction of siloxycyclopropanes with acid chlorides. A homoenolate route to 1,4-dicarbonyl compounds
  作者：Satoshi Aoki、Tsutomu Fujimura、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/s0040-4039(01)89016-x

  日期：1989.1
• Synthesis of 1,4-keto esters and 1,4-diketones via palladium-catalyzed acylation of siloxycyclopropanes. Synthetic and mechanistic studies
  作者：Tsutomu Fujimura、Satoshi Aoki、Eiichi Nakamura

  DOI：10.1021/jo00008a043

  日期：1991.4

  The reaction of a variety of siloxycyclopropanes with acid chlorides in the presence of a catalytic amount of a palladium/phosphine complex gives 1,4-dicarbonyl compounds to good yield. 1-Alkoxy-1-(trialkylsiloxy)-cyclopropanes react with both aromatic and aliphatic acid chlorides in chloroform to give 1,4-keto esters. Synthesis of 1,4-diketones by the acylation of 1-alkyl- or 1-aryl-1-siloxycyclopropanes has been achieved by carrying out the reaction if HMPA under 10-20 atm of carbon monoxide. Kinetics studies and product analysis revealed the unique mechanism of this reaction, which involves rate-determining cleavage of the strained cyclopropane carbon-carbon bond with a coordinatively unsaturated acylpalladium chloride complex. Ab initio calculations of hydroxylated cyclopropane model compounds showed that the unique reactivities of the siloxycyclopropanes may be correlated with the molecular orbital properties of these compounds rather than their ground-state structural properties.
• Synthesis of 4-keto pimelates by palladium-catalyzed carbonylativesymmetrical coupling of siloxycyclopropanes
  作者：Satoshi Aoki、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)80346-9

  日期：——
• AOKI, SATOSHI;FUJIMURA, TSUTOMU;NAKAMURA, EIICHI;KUWAJIMA, ISAO, TETRAHEDRON. LETT., 30,(1989) N7, C. 6541-6544
  作者：AOKI, SATOSHI、FUJIMURA, TSUTOMU、NAKAMURA, EIICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——
• FUJIMURA, TSUTOMU;AOKI, SATOSHI;NAKAMURA, EIICHI, J. ORG. CHEM., 56,(1991) N, C. 2809-2821
  作者：FUJIMURA, TSUTOMU、AOKI, SATOSHI、NAKAMURA, EIICHI

  DOI：——

  日期：——