2-(t-butyldimethylsiloxy)nonane | 272788-08-6

• 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: 2-(t-butyldimethylsiloxy)nonane
• 英文别名: 2-nonanol, tBDMS；tert-butyl-dimethyl-nonan-2-yloxysilane
• CAS: 272788-08-6
• 化学式: C₁₅H₃₄OSi
• 分子量: 258.52
• InChiKey: VEHNNYOZMMKKLL-UHFFFAOYSA-N

物化性质

• 沸点：
  261.6±8.0 °C(Predicted)
• 密度：
  0.811±0.06 g/cm3(Predicted)
• 保留指数：
  1382

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-(t-butyldimethylsiloxy)nonane 在 N-溴代丁二酰亚胺(NBS) 、 β-环糊精 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以72%的产率得到2-壬酮
  参考文献：
  名称：

  A Facile β-Cyclodextrin-Catalyzed Oxidative Deprotection of tert-Butyl­dimethylsilyl (TBDMS) Ethers with NBS in Water

  摘要：

  在水中的β-环糊精存在下，使用NBS处理TBDMS醚首次实现了硅-氧键的断裂，随后经氧化得到羰基化合物。

  DOI：

  10.1055/s-2005-861808
• 作为产物：
  描述：

  2-壬醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以94%的产率得到2-(t-butyldimethylsiloxy)nonane
  参考文献：
  名称：

  在无溶剂条件下使用叔丁基二甲基氯硅烷 (TBDMCS) 有效且化学选择性地保护醇和酚

  摘要：

  摘要 在无溶剂条件下，使用 TBDMCS/咪唑可以将各种类型的伯醇和仲醇和酚有效地转化为其相应的 TBDMS 醚。DMF 的消除，伴随着简单的非水后处理和反应的高速率提高，对于所提出的方法值得一提。该反应在仲醇存在下显示出对伯保护的绝对化学选择性。

  DOI：

  10.1080/10426509808045483

文献信息

• A high loading sulfonic acid-functionalized ordered nanoporous silica as an efficient and recyclable catalyst for chemoselective deprotection of tert-butyldimethylsilyl ethers
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1016/j.tetlet.2005.04.100

  日期：2005.7

  A high loading sulfonic acid-functionalized ordered nanoporous silica efficiently catalyzes the deprotection of a variety of alcoholic TBDMS (tert-butyldimethylsilyl)ethers in methanol. The catalyst shows high thermal stability (up to 240 degrees C) and can be recovered and reused for at least seven reaction cycles without loss of reactivity. This method can be used to deprotect TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols. (c) 2005 Elsevier Ltd. All rights reserved.
• Efficient Method for the Deprotection of <i>tert</i>-Butyldimethylsilyl Ethers with TiCl₄−Lewis Base Complexes:  Application to the Synthesis of 1β-Methylcarbapenems
  作者：Akira Iida、Hiroki Okazaki、Tomonori Misaki、Makoto Sunagawa、Akira Sasaki、Yoo Tanabe

  DOI：10.1021/jo0604484

  日期：2006.7.1

  TiCl4-Lewis base (AcOEt, CH3NO2) complexes smoothly deprotected tert-butyldimethylsilyl (TBDMS) ethers. The reaction velocity with these complexes, which seemed less reactive due to the influence of Lewis bases, was considerably greater than that with TiCl4 alone. Selective desilylations between aliphatic and aromatic TBDMS ethers (1 and 5), between 1 and benzyl, allyl, tosyl, methoxyphenyl, and chloroacetyl ethers (13, 14, 15, 16, and 17), and between TBDMS and TBDPS ethers (18 and 19) were successfully performed. Desilylation of TBDMS-aldol, acyloin, and beta-lactam analogues 9-12 proceeded smoothly due to anchimeric assistance by the neighboring carbonyl groups. The present method was successfully applied to the practical synthesis of 1 beta-methylcarbapenems 20a'-f'.
• EFFICIENT AND CHEMOSELECTIVE PROTECTION OF ALCOHOLS AND PHENOLS WITH <i>Tert</i>-BUTYLDIMETHYLCHLOROSILANE (TBDMCS) UNDER SOLVENT-FREE CONDITIONS
  作者：Habib Firouzabadi、Shahrad Etemadi、Babak Karimi、Ali Asghar Jarrahpour

  DOI：10.1080/10426509808045483

  日期：1998.12.1

  primary and secondary alcohols and phenols can be converted efficiently to their corresponding TBDMS ethers using TBDMCS/imidazole under solvent-free conditions. Elimination of DMF, accompanied with an easy non-aqueous work-up and a high rate enhancement of the reaction are worthy to be mentioned for the presented method. The reactions show absolute chemoselectivity for the protection of primary in the

  摘要 在无溶剂条件下，使用 TBDMCS/咪唑可以将各种类型的伯醇和仲醇和酚有效地转化为其相应的 TBDMS 醚。DMF 的消除，伴随着简单的非水后处理和反应的高速率提高，对于所提出的方法值得一提。该反应在仲醇存在下显示出对伯保护的绝对化学选择性。
• A Facile β-Cyclodextrin-Catalyzed Oxidative Deprotection of <i>tert</i>-Butyl­dimethylsilyl (TBDMS) Ethers with NBS in Water
  作者：K. Rao、M. Reddy、M. Narender、Y. Nageswar

  DOI：10.1055/s-2005-861808

  日期：——

  Treatment of TBDMS ethers with NBS in the presence of β-cyclodextrin in water results, for the first time, in the cleavage of the silicon-oxygen bond, carbonyl compounds are obtained upon oxidation.

  在水中的β-环糊精存在下，使用NBS处理TBDMS醚首次实现了硅-氧键的断裂，随后经氧化得到羰基化合物。