(cyclohexyloxy)diphenylmethylsilane | 20466-56-2

• 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: (cyclohexyloxy)diphenylmethylsilane
• 英文别名: 1-Diphenyl(methyl)silyloxycyclohexane；cyclohexyloxy-methyl-diphenylsilane
• CAS: 20466-56-2
• 化学式: C₁₉H₂₄OSi
• 分子量: 296.484
• InChiKey: XXDZOLHJHHBVBK-UHFFFAOYSA-N

物化性质

• 沸点：
  189-191 °C(Press: 5 Torr)
• 密度：
  1.0285 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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 (cyclohexyloxy)diphenylmethylsilane
  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

• Scope and selectivity of B(C6F5)3-catalyzed reactions of the disilane (Ph2SiH)2
  作者：Peter T.K. Lee、Lisa Rosenberg

  DOI：10.1016/j.jorganchem.2016.02.035

  日期：2016.5

  harnessing the collective, broad scope of these transformations in the preparation of new oligosilane derivatives. Borane-catalyzed hydrosilation, heterodehydrogenative coupling, and dealkylative coupling reactions of a wide range of substrates with the disilane (Ph2SiH)2 were investigated. These allowed new mono- and disubstituted disilanes to be prepared that contain SiO, SiS, and SiC linkages. Challenges

  硅烷与有机底物反应中的亲电硼烷B（C 6 F 5）3的各种催化活性已在研究中得到了广泛利用，这些研究主要集中于有机合成中非常特殊，有用的官能团转化。这项研究检验了在制备新的低聚硅烷衍生物中利用这些转变的集体广泛范围的潜力。研究了硼烷催化的氢化硅烷化，杂脱氢偶联和各种基材与乙硅烷（Ph 2 SiH）2的脱烷基偶联反应。这些使得可以制备含有Si O，Si S和Si的新的单取代和二取代的乙硅烷。C链接。描述了竞争性“过度还原”化学反应所带来的挑战和机遇，并研究了催化对底物的路易斯碱度和空间位阻的敏感性。
• Potassium<i>tert</i>-Butoxide-Catalyzed Dehydrogenative SiO Coupling: Reactivity Pattern and Mechanism of an Underappreciated Alcohol Protection
  作者：Andreas Weickgenannt、Martin Oestreich

  DOI：10.1002/asia.200800426

  日期：2009.3.2

  As simple as it gets! Potassium tert‐butoxide alone catalyzes the direct dehydrogenative SiO coupling of several synthetically important silanes with 1°, 2°, and even 3° alcohols without the need for stoichiometric hydrochloric acid scavengers. The stereoretentive mechanism is probed with a silicon‐stereogenic silane.

  就这么简单！钾叔丁醇单独催化直接脱氢的Si 的几个合成重要硅烷与1 O联接°，2°，甚至3°醇，而不需要化学计量的盐酸清除剂。立体固位机理是通过硅立体烷硅烷来探测的。
• Nickel‐Catalyzed Selective Cross‐Coupling of Chlorosilanes with Organoaluminum Reagents
  作者：Yuki Naganawa、Haiqing Guo、Kei Sakamoto、Yumiko Nakajima

  DOI：10.1002/cctc.201900047

  日期：2019.8.21

  Nickel‐catalyzed cross‐coupling reactions of chlorosilanes with organoaluminum reagents were developed. An electron‐rich Ni(0)/PCy3 complex was found to be an effective catalyst for the desired transformation. The reaction of dichlorosilanes 1 proceeded to give the corresponding monosubstituted products 2. Trichlorosilanes 4 underwent selective double substitution to furnish the corresponding monochlorosilanes

  开发了镍催化的氯硅烷与有机铝试剂的交叉偶联反应。发现富电子的Ni（0）/ PCy 3络合物是实现所需转化的有效催化剂。进行二氯硅烷1的反应，得到相应的单取代的产物2。对三氯硅烷4进行选择性双取代，以提供相应的一氯硅烷2。总体而言，使用本发明的催化体系可以从二氯和三氯硅烷选择性合成一系列烷基一氯硅烷2。
• N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds
  作者：Uǧur Kaya、Uyen P. N. Tran、Dieter Enders、Junming Ho、Thanh V. Nguyen

  DOI：10.1021/acs.orglett.7b00306

  日期：2017.3.17

  N-Heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocyclic carbenes (NHCs), have recently emerged as a new family of promising organocatalysts with strong nucleophilicity and Brønsted basicity. The development of a novel method is shown using NHOs as efficient promoters for the direct dehydrogenative silylation of alcohols or hydrosilylation of carbonyl compounds. Preliminary results

  N-杂环卡宾（NHC）的亚烷基衍生物N-杂环烯烃（NHOs）最近成为具有强亲核性和布朗斯台德碱度的新的有前途的有机催化剂家族。使用NHOs作为醇类直接脱氢甲硅烷基化或羰基化合物氢化硅烷化的有效促进剂，表明了一种新方法的开发。还讨论了第一个NHO促进的不对称合成的初步结果。
• Chemoselektive mono- und disilyletherbildung aus tertiären und sekundären silanen
  作者：Leopold Horner、Johann Mathias

  DOI：10.1016/0022-328x(85)87167-9

  日期：1985.3