4-(tert-butyl-dimethylsilanyloxy)-butyl 3-phenylpropanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(tert-butyl-dimethylsilanyloxy)-butyl 3-phenylpropanoate
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxybutyl 3-phenylpropanoate
• 化学式: C₁₉H₃₂O₃Si
• 分子量: 336.547
• InChiKey: IUTCOLCYWJSCQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯丙酸乙酯 、 4-(叔丁基二甲基甲硅烷基)氧代-1-丁醇 在 iron(III)-acetylacetonate 、 sodium carbonate 作用下， 以 正庚烷 为溶剂， 反应 7.0h， 以94%的产率得到4-(tert-butyl-dimethylsilanyloxy)-butyl 3-phenylpropanoate
  参考文献：
  名称：

  Transesterification catalyzed by iron(III) β-diketonate species

  摘要：

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.009

文献信息

• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
  作者：Guillaume Force、Anna Perfetto、Robert J. Mayer、Ilaria Ciofini、David Lebœuf

  DOI：10.1002/anie.202105882

  日期：2021.9

  towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables

  大环内酯是一类特殊的天然和合成产品，在精细化学品和制药行业有着广泛的应用。尽管在合成方面取得了所有进展，特别是从seco-酸，一种有效的、选择性的、灵活的、容易获得的并且尽可能与多种官能团相容的大环内酯化促进剂系统仍然缺乏。在这里，我们描述了一种策略，该策略依赖于形成包含五氟苯基的混合酸酐，由于其高电子活化，可以方便地获得具有广泛多功能性的大环内酯、大二内酯和酯。进行动力学研究和 DFT 计算以合理化五氟苯基在大环内酯化反应中的反应性。
• Direct Esterification of Carboxylic Acids with Alcohols Catalyzed by Iron(III) Acetylacetonate Complex
  作者：Shiue-Shien Weng、Fong-Kuang Chen、Chih-Shueh Ke

  DOI：10.1080/00397911.2012.725265

  日期：2013.10.2

  Abstract Direct condensation of carboxylic acids and alcohols with electronic, steric, and functional group variations was carried out using the environmentally benign, moisture-stable, inexpensive, and recoverable iron(III) acetylacetonate [Fe(acac)3] as catalyst (5 mol%). This iron salt efficiently catalyzed the esterification of several primary and secondary alcohols in refluxing xylene, without the need

  摘要 使用环境友好、耐湿、廉价且可回收的乙酰丙酮铁 (III) [Fe(acac)3] 作为催化剂 (5 mol) 进行具有电子、空间和官能团变化的羧酸和醇的直接缩合反应。 %）。这种铁盐有效地催化了回流二甲苯中几种伯醇和仲醇的酯化反应，而无需脱水试剂。通过用苯甲酸对外消旋 1-苯基乙烷-1,2-二醇中的伯醇官能团进行选择性酯化，证明了所提议方案的化学选择性。酯化也适用于未掩蔽的 α-羟基酸、guasaromatic、杂环和 N-保护的氨基酸。补充材料可用于本文。去出版商' 的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Direct Atom-Efficient Esterification between Carboxylic Acids and Alcohols Catalyzed by Amphoteric, Water-Tolerant TiO(acac)₂
  作者：Chien-Tien Chen、Yogesh S. Munot

  DOI：10.1021/jo051337s

  日期：2005.10.1

  [GRAPHIC]A diverse array of oxometallic species were examined as catalysts for a test direct condensation of benzoic acid and 2-phenylethanol in 1:1 stoichiometry. Besides group IVB MOCl2-xH(2)O and TiOX2-xH(2)O, group VB VOCl2-xTHF and group IVB TiO(acac)(2) were found to be the most efficient and water-tolerant catalysts for the test reaction. The new neutral catalytic protocol with the optimal TiO(acac)2 tolerates many stereo/electronic structural variations in both (di)acid (1 degrees-3 degrees alkyl and aryl) and (di)alcohol (1 degrees, 2 degrees alkyl, and aryl) components with high chemoselectivity.
• Transesterification catalyzed by iron(III) β-diketonate species
  作者：Shiue-Shien Weng、Chih-Shueh Ke、Fong-Kuang Chen、You-Fu Lyu、Guan-Ying Lin

  DOI：10.1016/j.tet.2011.01.009

  日期：2011.3

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.