3-((tert-butyldimethylsilyl)oxy)-1-oxo-1-phenylpropan-2-yl 4-nitrobenzoate | 1456890-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((tert-butyldimethylsilyl)oxy)-1-oxo-1-phenylpropan-2-yl 4-nitrobenzoate
• 英文别名: 3-((tert-butyldimethylsilyl)oxy)-1-oxo-1-phenylpropan-2-yl-4-nitrobenzoate；[3-[Tert-butyl(dimethyl)silyl]oxy-1-oxo-1-phenylpropan-2-yl] 4-nitrobenzoate；[3-[tert-butyl(dimethyl)silyl]oxy-1-oxo-1-phenylpropan-2-yl] 4-nitrobenzoate
• CAS: 1456890-76-8
• 化学式: C₂₂H₂₇NO₆Si
• 分子量: 429.545
• InChiKey: VHPYDOVGFUQJSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene 、 苯甲酸 在 叔丁基过氧化氢 、 碘 、 三乙胺 作用下， 以 癸烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 以84%的产率得到3-((tert-butyldimethylsilyl)oxy)-1-oxo-1-phenylpropan-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  I₂-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives

  摘要：

  I-2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of a-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I-2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3 center dot SMe2 leading to monoprotected diol derivatives in excellent yields.

  DOI：

  10.1021/ol5027393

文献信息

• N-Heterocyclic carbene catalyzed regioselective oxo-acyloxylation of alkenes with aromatic aldehydes: a high yield synthesis of α-acyloxy ketones and esters
  作者：Rambabu N. Reddi、Pushpa V. Malekar、Arumugam Sudalai

  DOI：10.1039/c3ob41551a

  日期：——

  An N-heterocyclic carbene (NHC)-catalyzed reaction of alkenes with aromatic aldehydes providing for a high yield synthesis of α-acyloxy ketones and esters has been described. This unprecedented regioselective oxidative process employs NBS and Et3N in stoichiometric amounts and O2 (1 atm) as an oxidant under ambient conditions in DMSO as a solvent.

  已经描述了烯烃与芳族醛的N-杂环卡宾（NHC）催化的反应，提供了高产率的α-酰氧基酮和酯的合成。这种史无前例的区域选择性氧化方法在化学条件下，以DMSO为溶剂，使用化学计量的NBS和Et 3 N和O 2（1 atm）作为氧化剂。
• [EN] ONE STEP PROCESS FOR REGIOSELECTIVE SYNTHESIS OF α-ACYLOXY CARBONYLS<br/>[FR] PROCÉDÉ EN UNE ÉTAPE POUR LA SYNTHÈSE RÉGIOSÉLECTIVE D'&Agr;-ACYLOXY CARBONYLES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014195972A1

  公开（公告）日：2014-12-11

  A regioselective N-Heterocyclic Carbene (NHC) catalyzed one step process for high yield synthesis of α-acyloxy carbonyl compounds is disclosed.

  揭示了一种选择性区域N-杂环卡宾（NHC）催化的一步法，用于高产率合成α-酰氧羰基化合物。
• I₂-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives
  作者：Rambabu N. Reddi、Pragati K. Prasad、Arumugam Sudalai

  DOI：10.1021/ol5027393

  日期：2014.11.7

  I-2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of a-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I-2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3 center dot SMe2 leading to monoprotected diol derivatives in excellent yields.