cyclopentyloxy(methyl)diphenylsilane | 135746-50-8

• 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: cyclopentyloxy(methyl)diphenylsilane
• 英文别名: 1-Diphenyl(methyl)silyloxycyclopentane；cyclopentyloxy-methyl-diphenylsilane
• CAS: 135746-50-8
• 化学式: C₁₈H₂₂OSi
• 分子量: 282.458
• InChiKey: IXNPYDHRKPFPQP-UHFFFAOYSA-N

物化性质

• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基二苯基氯硅烷 在 正丁基锂 、 偶氮二异丁腈 、 Celite 、 三氟化硼乙醚 、 三正丁基氢锡 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 5.0h， 生成 cyclopentyloxy(methyl)diphenylsilane
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302

文献信息

• [2.2]Paracyclophane derived bisphosphines for the activation of hydrogen by FLPs: application in domino hydrosilylation/hydrogenation of enones
  作者：Lutz Greb、Pascual Oña-Burgos、Adam Kubas、Florian C. Falk、Frank Breher、Karin Fink、Jan Paradies

  DOI：10.1039/c2dt30374d

  日期：——

  The heterolytic splitting of hydrogen by two types of [2.2]paracyclophane derived bisphosphines (1, 2a and 2b) in combination with tris(pentafluorophenyl)borane (3) at room temperature is described. The corresponding frustrated Lewis pairs (FLPs) exhibit different behavior in the activation of hydrogen. This results from diverse steric and electronic properties of the bisphosphines. The reactivity of the frustrated Lewis pairs was exploited in the first diastereoselective domino hydrosilylation/hydrogenation reaction catalyzed by FLPs.

  描述了两种[2.2]对环苯烃衍生的双磷烯（1、2a和2b）与三（五氟苯基）硼烷（3）在室温下进行氢的异裂。相应的受挫路易斯对（FLPs）在氢的活化过程中表现出不同的行为。这是由于双磷烯的立体和电子性质各不相同。受挫路易斯对的反应性在首个催化FLPs的非对映选择性多米诺氢硅化/氢化反应中得到了利用。
• Intramolecular free radical cyclizations using acylsilanes as radicalphiles
  作者：Yeun-Min Tsai、Chaur-Donp Cherng

  DOI：10.1016/0040-4039(91)80820-v

  日期：1991.7

  Carbon radicals add intramolecularly to acylsilanes at the carbonyl carbon followed by radical Brook rearrangement to give silylated cyclopentanols or cyclohexanols in good yields.
• The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals
  作者：Sheng-Yueh Chang、Weir-Torn Jiaang、Chaur-Donp Cherng、Kuo-Hsiang Tang、Chih-Hao Huang、Yeun-Min Tsai

  DOI：10.1021/jo9711302

  日期：1997.12.1

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.