trimethyl[(2-methyl-1-phenylpropan-2-yl)oxy]silane

• 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: trimethyl[(2-methyl-1-phenylpropan-2-yl)oxy]silane
• 英文别名: Trimethyl-(2-methyl-1-phenylpropan-2-yl)oxysilane
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: PBQMNBBTFSURGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  trimethyl[(2-methyl-1-phenylpropan-2-yl)oxy]silane 在 水 、 对甲苯磺酰氯 作用下， 反应 0.42h， 以60%的产率得到二甲基苄基原醇
  参考文献：
  名称：

  对甲苯磺酰氯 (p-TsCl)-使用六甲基二硅氮烷催化羟基三甲基甲硅烷基化及其在温和条件下的再生：对甲苯磺酰氯催化应用的第一个例子

  摘要：

  报道了对甲苯磺酰氯 (p-TsCl) 在二氯甲烷中与六甲基二硅氮烷 (HMDS) 对各种类型的羟基进行有效和选择性的三甲基甲硅烷基化以及这些化合物在水中的脱甲硅烷基化的首次催化应用。反应在室温下进行，发现以良好到极好的产率进行。

  DOI：

  10.1080/10426500802453872
• 作为产物：
  描述：

  二甲基苄基原醇 、 叠氮基三甲基硅烷 在 四丁基溴化铵 作用下， 反应 0.5h， 以98%的产率得到trimethyl[(2-methyl-1-phenylpropan-2-yl)oxy]silane
  参考文献：
  名称：

  Efficient O-Trimethylsilylation of Alcohols and Phenols with Trimethylsilyl Azide Catalyzed by Tetrabutylammonium Bromide under Neat Conditions

  摘要：

  A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 degreesC. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.

  DOI：

  10.1021/jo015814s

文献信息

• H₅IO₆/KI: A New Combination Reagent for Iodination of Aromatic Amines, and Trimethylsilylation of Alcohols and Phenols through<i>in situ</i>Generation of Iodine under Mild Conditions
  作者：Mohammad Ali Zolfigol、Ardeshir Khazaei、Eskandar Kolvari、Nadiya Koukabi、Hamid Soltani、Maryam Behjunia

  DOI：10.1002/hlca.200900259

  日期：2010.3

  A simple method for the in situ generation of iodine using H5IO6/KI has been developed, and its application in silylation of OH group and iodination of aromatic amines is described.

  已开发出一种使用H 5 IO 6 / KI原位生成碘的简单方法，并描述了其在OH基甲硅烷基化和芳族胺碘化中的应用。
• Efficient Trimethylsilylation of Alcohols and Phenols with HMDS in the Presence of a Catalytic Amount of 1,3-Dibromo-5,5-Dimethylhydantoin (DBDMH) as a Safe and Cheap Industrial Chemical
  作者：Ardeshir Khazaei、Amin Rostami、Marjan Mahboubifar

  DOI：10.1002/jccs.200700068

  日期：2007.4

  1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) is found to be an effective catalyst for trimethylsilylation various alcohols and phenols with hexamethyldisilazane (HMDS) in dichloromethane at room temperature.

  1,3-二溴-5,5-二甲基乙内酰脲 (DBDMH) 被发现是在室温下在二氯甲烷中用六甲基二硅氮烷 (HMDS) 三甲基硅烷化各种醇和酚的有效催化剂。
• 1,3-Dichloro-5,5-Dimethylhydantoin (DCH) and Trichloromelamine (TCM) as Efficient Catalysts for the Chemoselective Trimethylsilylation of Hydroxyl Group with 1,1,1,3,3,3-Hexamethyldisilazane (HMDS) Under Mild Conditions
  作者：Arash Ghorbani-Choghamarani、Kamal Amani、Mohammad Ali Zolfigol、Maryam Hajjami、Roia Ayazi-Nasrabadi

  DOI：10.1002/jccs.200900037

  日期：2009.4

  A highly convenient method for the trimethylsilylation of alcohols and phenols via treatment by hexamethyldisilazane in the presence of 1,3–dichloro‐5,5–dimethylhydantoin (DCH) and/or trichloromelamine (TCM) as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected in CH2Cl2/CH3CN under mild conditions.

  已经开发了一种非常方便的方法，用于在1，3-二氯-5，5-二甲基乙内酰脲（DCH）和/或三氯三聚氰胺（TCM）作为催化剂存在下，通过六甲基二硅氮烷进行处理，对醇和酚进行三甲基甲硅烷基化。在温和的条件下，在CH 2 Cl 2 / CH 3 CN中选择性保护了多种羟基。
• Protection of hydroxy groups as trimethylsilyl ethers using 1,1,1,3,3,3-hexamethyldisilazane (HMDS) catalyzed by poly(4-vinylpyridinium tribromide)
  作者：Arash Ghorbani-Choghamarani、Mohammad Ali Zolfigol、Maryam Hajjami、Khorshid Darvishi、Laleh Gholamnia

  DOI：10.1135/cccc2009560

  日期：——

  A very efficient procedure for the protection of alcohols and phenols is presented. The mixture of 1,1,1,3,3,3-hexamethyldisilazane (HMDS) and catalytic amounts of poly(4-vinylpyridinium tribromide) was found to be effective for the trimethylsilylation of alcohols and phenols. Protection reaction is very simple and performs heterogeneously in acetonitrile at room temperature under mild conditions.

  一种非常高效的醇和酚保护程序被提出。发现1,1,1,3,3,3-六甲基二硅氮烷（HMDS）与聚（4-乙烯吡啶三溴化物）的催化量混合物对醇和酚的三甲基硅基化是有效的。保护反应非常简单，在室温下在乙腈中以温和条件异相进行。
• {[[K.18-Crown-6]Br3}n: A tribromide catalyst for the catalytic protection of amines and alcohols
  作者：Gholamabbas Chehardoli、Mohammad Ali Zolfigol、Fateme Derakhshanpanah

  DOI：10.1016/s1872-2067(12)60644-5

  日期：2013.9

  [K.18-Crown-6]Br3}n, a unique tribromide-type catalyst, was utilized for the N-boc protection of amines and trimethylsilylation (TMS) and tetrahydropyranylation (THP) of alcohols. The method is general for the preparation of N-boc derivatives of aliphatic (acyclic and cyclic) and aromatic, and primary and secondary amines and also various TMS-ethers and THP-ethers. The simple separation of the catalyst

  摘要 [K.18-Crown-6]Br3}n 是一种独特的三溴化物型催化剂，用于胺的 N-boc 保护以及醇的三甲基硅烷化 (TMS) 和四氢吡喃化 (THP)。该方法通常用于制备脂肪族（无环和环状）和芳香族的 N-boc 衍生物、伯胺和仲胺以及各种 TMS-醚和 THP-醚。催化剂与产品的简单分离是该方法的众多优点之一。