(indan-5-yloxy)trimethylsilane | 502470-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (indan-5-yloxy)trimethylsilane
• 英文别名: [(2,3-Dihydro-1H-inden-5-yl)oxy](trimethyl)silane；2,3-dihydro-1H-inden-5-yloxy(trimethyl)silane
• CAS: 502470-28-2
• 化学式: C₁₂H₁₈OSi
• 分子量: 206.36
• InChiKey: HGKGSBUSUIVLQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (indan-5-yloxy)trimethylsilane 在 水 、 硼酸 作用下， 反应 2.6h， 以80%的产率得到5-茚醇
  参考文献：
  名称：

  Boric acid as cost-effective and recyclable catalyst for trimethylsilyl protection and deprotection of alcohols and phenols

  摘要：

  Boric acid has been used as a green, selective and recyclable catalyst for trimethysilylation of alcohols and phenols using hexamethyldisilazane in acetonitrile. Deprotection of trimethylsilyl ethers to their parent alcohols and phenols was also achieved using this catalyst in water at room temperature. The salient features of this methodology are cheap processing, mild acidity conditions, excellent yields of products and easy availability of the catalyst.

  DOI：

  10.1590/s0103-50532010000800026
• 作为产物：
  描述：

  5-茚醇 、 六甲基二硅氮烷 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 1.0h， 以95%的产率得到(indan-5-yloxy)trimethylsilane
  参考文献：
  名称：

  N-Bromosuccinimide (NBS) — Selective and effective catalyst for trimethylsilylation of alcohols and phenols using hexamethyldisilazane and their regeneration under mild and neutral reaction conditions

  摘要：

  在室温下的二氯甲烷和无溶剂条件下，使用一定量的 N-溴代琥珀酰亚胺催化剂，通过与六甲基二硅氮烷（HMDS）进行清洁高效的反应，实现了结构多样的醇和酚的三甲基硅烷化。在催化量 NBS 的存在下，在室温下的甲醇中也能有效地实现三甲基硅基醚的脱保护：N-溴代丁二酰亚胺、无溶剂、醇、酚、六甲基二硅氮烷、三甲基硅基醚、催化剂、去甲基硅烷化。

  DOI：

  10.1139/v07-029

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。
• Novel and Highly Effective Method for the Trimethylsilylation of Alcohols and Phenols with Hexamethyldisilazane (HMDS), Catalyzed by I₂Generated<i>in situ</i>Using Fe(NO₃)₃⋅9 H₂O/NaI under Heterogeneous and Neutral Conditions
  作者：Ardeshir Khazaei、Sadegh Rahmati、Amin Rostami

  DOI：10.1002/hlca.200900002

  日期：2009.7

  Structurally diverse alcohols and phenols were trimethylsilylated in a clean and efficient reaction with hexamethyldisilazane (HMDS) based on the use of I2 generated in situ from Fe(NO3)3⋅9 H2O/NaI. The reaction occurs very rapid in good‐to‐high yield in CH2Cl2 at room temperature, and the use of toxic and corrosive molecular I2 is avoided.

  结构不同的醇和酚是在用六甲基二硅烷（HMDS）清洁和有效的反应基于使用的我三甲基甲硅烷2产生原位选自Fe（NO 3）3 ⋅9ħ 2 O /碘化钠。在室温下，该反应在CH 2 Cl 2中以高至高收率非常迅速地发生，并且避免使用有毒和腐蚀性的分子I 2。
• Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalysed by in situ generated I 2 using Oxone®/KI or cerium ammonium nitrate (CAN)/KI systems under mild conditions
  作者：Eskandar Kolvari、Ardeshir Khazaei、Mohammad Ali Zolfigol、Nadiya Koukabi、Maryam Gilandoust、Neda Bakhit

  DOI：10.1007/s12039-011-0120-5

  日期：2011.9

  Structurally diverse alcohols and phenols were trimethylsilylated in clean and efficient reactions with hexamethyldisilazane (HMDS) in the presence of a catalytic amount of I2 generated in situ from Oxone®/KI or CAN/KI systems. The reactions occur rapidly in good to high yields in wet CH2Cl2 at room temperature.

  结构多样化的醇和酚在六甲基二硅氮烷（HMDS）存在下与由Oxone®/KI或CAN/KI体系原位生成的催化量碘进行的反应中，以清洁高效的方式进行了三甲基硅烷化。这些反应在室温下在湿润的氯仿中迅速进行，产率良好至高。
• Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
  作者：Marjan Jereb

  DOI：10.1016/j.tet.2012.03.040

  日期：2012.5

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.
• <i>N,N</i>′-Dibromo-<i>N,N</i>′-1,2-ethanediylbis (Benzene Sulfonamide) as a Novel <i>N</i>-Bromo Reagent–Catalyzed Trimethylsilylation of Alcohols and Phenol With Hexamethyldisilazane in Both Solution and Solvent-Free Conditions
  作者：Ardeshir Khazaei、Amin Rostami、Sadegh Rahmati、Marjan Mahboubifar

  DOI：10.1080/10426500601013232

  日期：2007.4.1

  Preparation and catalytic application of N,N'-dibromo-N,N'-1,2-ethanediylbis (benzene sulfonamide) for the trimethylsilylation of several of alcohols and phenols with hexamethyldisilazane in good to excellent yields under both solution and solvent-free conditions at r.t. is descried.