(1-biphenyl-4-yl-1-methyl-ethoxy)trimethylsilyl ether | 669055-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1-biphenyl-4-yl-1-methyl-ethoxy)trimethylsilyl ether
• 英文别名: trimethyl-[2-(4-phenylphenyl)propan-2-yloxy]silane
• CAS: 669055-44-1
• 化学式: C₁₈H₂₄OSi
• 分子量: 284.473
• InChiKey: CPESMVJKXDJJGB-UHFFFAOYSA-N

物化性质

• 沸点：
  348.9±11.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1-biphenyl-4-yl-1-methyl-ethoxy)trimethylsilyl ether 在 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate 、 溴 作用下， 反应 12.0h， 以69%的产率得到1-(2-Bromopropan-2-yl)-4-phenylbenzene
  参考文献：
  名称：

  一种新型的二苯基次膦酸酯离子液体（IL-OPPh 2）作为试剂和溶剂，用于醇和三甲基甲硅烷基和四氢吡喃基醚的高度选择性溴化，硫氰化或异硫氰化

  摘要：

  介绍了一种新型的二苯基次膦酸酯离子液体（IL-OPPh 2）。这种离子液体用作两者的试剂和转换醇和三甲基甲硅烷和四氢吡喃基（THP）溶剂醚类为它们相应的烷基溴化物，硫氰酸盐或异硫氰酸盐在溴的存在下2和SCN -在80℃下。在这种离子液体中，在三甲基甲硅烷基和THP-醚的存在下以及在不同类别的醇之间，醇的溴化和硫氰化反应会高度选择性地发生。该离子液体的使用使得所需的产物易于从次膦酸酯副产物中分离出来。

  DOI：

  10.1016/j.tetlet.2006.05.145
• 作为产物：
  描述：

  2-(4-联苯基)-2-丙醇 、 六甲基二硅氮烷 在 N,N',N'',N'''-Me₄-tetra-2,3-pyridinoporphyrazinato Cu(II) 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以95%的产率得到(1-biphenyl-4-yl-1-methyl-ethoxy)trimethylsilyl ether
  参考文献：
  名称：

  N,N',N",N‴-TetramethylLTETRA-2,3-Pyridinoporphyrazinato Copper (II) 中的六甲基二硅氮烷是一种新型、温和且高效的醇和酚甲硅烷基化试剂

  摘要：

  在 N,N',N',N‴-tetramethyletra-2,3-pyridinoporphyrazinato 铜 (II) 的存在下，醇类和酚类在室温下用六甲基二硅氮烷保护，收率从好到极好。

  DOI：

  10.1080/10426500490474987

文献信息

• Iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available, non-hygroscopic, non-corrosive, highly stable and a reusable Lewis Acid catalyst: Efficient O-silylation of α-hydroxyphosphonates, alcohols and phenols by hexamethyldisilazane (HMDS) under solvent-free conditions
  作者：Habib Firouzabadi、Nasser Iranpoor、Abbas Ali Jafari、Mohammad Reza Jafari

  DOI：10.1016/j.jorganchem.2008.05.018

  日期：2008.8

  O-Silylation of hydroxyl groups of α-hydroxyphosphonates, primary, secondary tertiary-alcohols and phenols with HMDS was achieved in high to excellent yields using iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available and a cost effective, non-hygroscopic, non-corrosive, highly stable and an efficient catalyst under solvent-free conditions. As a typical reaction, we have scaled up silylation of diphenyl

  ø α-hydroxyphosphonates，伯，仲叔醇和酚与HMDS的羟基-Silylation在实现高使用铁（III）三氟乙酸盐的[Fe（F优异的产率3 CCO 2）3 ]作为容易获得和在无溶剂条件下具有成本效益，不吸湿，不腐蚀，高度稳定和高效的催化剂。作为典型的反应，我们已将二苯甲醇的甲硅烷基化规模扩大到20 mmol的底物，以证明该催化剂对于规模化生产非常有效。通过简单的过滤就可以容易地分离出催化剂，并且可以循环使用该催化剂进行二苯甲硅烷基化反应，而不会失去其催化活性。
• Chlorodiphenylphosphine as Highly Selective and Efficient Reagent for the Conversion of Alcohols, Tetrahydropyranyl and Silyl Ethers to Thiocyanates and Isothiocyanates
  作者：Ghasem Aghapour、Ameneh Asgharzadeh

  DOI：10.1080/10426507.2013.855771

  日期：2014.6.3

  efficient method is described for the conversion of primary alcohols, tetrahydropyranyl and silyl ethers to thiocyanates by use of chlorodiphenylphosphine and ammonium thiocyanate. Secondary substrates produce both the two isomeric products, thiocyanate and isothiocyanate, while tertiary ones give isothiocyanates as the only products by this new method. In contrast to previously reported methods based

  摘要 描述了一种使用氯二苯基膦和硫氰酸铵将伯醇、四氢吡喃基和甲硅烷基醚转化为硫氰酸酯的简单、高选择性和高效的方法。二级底物产生两种异构产物，硫氰酸盐和异硫氰酸盐，而三级底物通过这种新方法产生异硫氰酸盐作为唯一的产物。与之前报道的基于三价磷进行这种转化的方法相比，本方法在三价磷 (ClPPh2) 存在下不需要亲电试剂。这些底物的活性顺序是甲硅烷基醚>醇>四氢吡喃基醚。本方法不仅有趣地区分了初级，二级和三级底物，但也将它们转化为相应的硫氰酸盐，在存在几个其他官能团的情况下具有出色的化学选择性。图形概要
• Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system
  作者：Nasser Iranpoor、Habib Firouzabadi、Najmeh Nowrouzi

  DOI：10.1016/j.tet.2006.03.030

  日期：2006.6

  A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1° and 2° alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3° ones to isothiocyanates in good to high yields.

  三苯基膦（PPh 3）和2,3-二氯-5,6-二氰基苯并醌（DDQ）的组合提供了一种安全且易于使用的混合试剂体系，可用于转化1°和2°醇，硫醇，三甲基甲硅烷基和四氢吡喃基醚转化为相应的硫氰酸酯，3°异构化为异硫氰酸酯，收率高至高。
• Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
  作者：Farhad Shirini、Nader Ghaffari Khaligh、Somayeh Akbari-Dadamahaleh

  DOI：10.1016/j.molcata.2012.08.002

  日期：2012.12

  Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR. H-1 NMR, C-13 NMR and MS studies. All the products were extensively characterized by IR, H-1 NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification. (C) 2012 Elsevier B.V. All rights reserved.
• Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool, Synthesis, 2004, # 1, p. 92 - 96
  作者：Iranpoor, Nasser、Firouzabadi, Habib、Akhlaghinia, Batool、Azadi, Roya

  DOI：——

  日期：——