phenylacetic acid triisopropylsilyl ester | 105041-12-1

• 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: phenylacetic acid triisopropylsilyl ester
• 英文别名: triisopropylsilyl phenylacetate；Tri(propan-2-yl)silyl 2-phenylacetate
• CAS: 105041-12-1
• 化学式: C₁₇H₂₈O₂Si
• 分子量: 292.494
• InChiKey: VSUCDMYZYYUOHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.2±21.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenylacetic acid triisopropylsilyl ester 在 lithium acetate 、 水 、 N,N-二甲基甲酰胺 作用下， 反应 0.25h， 以96%的产率得到苯乙酸
  参考文献：
  名称：

  DMF-mediated deprotection of bulky silyl esters under neutral and fluoride-free conditions

  摘要：

  Bulky TBDPS and TIPS carboxylic esters were efficiently cleaved by a green and mild protocol using only DMF-H2O (20:1) at 70 degrees C. The neutral conditions tolerate various common acid- and base-labile functionalities, including alkyl and aryl silyl ethers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.048
• 作为产物：
  描述：

  苯乙酸 、 1-Triisopropylsilanyl-1H-imidazole 生成 phenylacetic acid triisopropylsilyl ester
  参考文献：
  名称：

  EFFECTIVE SILYLATION OF CARBOXYLIC ACIDS UNDER SOLVENT-FREE CONDITIONS WITH tert-BUTYLDIMETHYLSILYL CHLORIDE (TBDMSCL) AND TRIISOPROPYLSILYL CHLORIDE (TIPSCL)

  摘要：

  Various types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2 degrees, 3 degrees hydroxyl groups are observed.

  DOI：

  10.1080/10426500008076532

文献信息

• Preparation of silyl polyenol ethers by carbonyl olefination of silyl esters
  作者：Takeshi Takeda、Tatsuya Fukada、Akira Tsubouchi

  DOI：10.1016/j.tetlet.2014.01.040

  日期：2014.2

  Silyl enol ethers were produced by the carbonyl olefination of silyl esters with titanium carbene complexes generated by the desulfurizative titanation of thioacetals. The regioselective preparation of silyl dienol and trienol ethers has been achieved by using unsaturated silyl esters and thioacetals.

  甲硅烷基烯醇醚是通过将甲硅烷基酯的羰基烯化与硫代乙缩醛的脱硫钛化反应生成的钛碳烯配合物而制得的。甲硅烷基二烯醇和三烯醇醚的区域选择性制备已经通过使用不饱和甲硅烷基酯和硫代缩醛实现。
• Solvent-modulated chemoselective deprotections of trialkylsilyl esters and chemoselective esterifications
  作者：Adam Shih-Yuan Lee、Feng-Yih Su

  DOI：10.1016/j.tetlet.2005.07.049

  日期：2005.9

  A series of trialkylsilyl esters were deprotected or transesterificated into their corresponding carboxylic acids or methyl esters under a catalytic amount of CBr4 in alcohol reaction system. This method enables to desilylate secondary sp3-carbon, sp2-carbon, sp-carbon and aryl tethered trialkylsilyl esters to carboxylic acids, whereas primary sp3-carbon tethered trialkylsilyl esters were further converted

  在醇反应体系中，在催化量的CBr 4下，将一系列的三烷基甲硅烷基酯脱保护或酯交换成它们相应的羧酸或甲酯。该方法使得能够将仲sp 3-碳，sp 2-碳，sp-碳和芳基系链的三烷基甲硅烷基酯脱甲硅烷基化为羧酸，而将sp 3-碳系链的三烷基甲硅烷基酯进一步在CBr 4 / MeOH反应下转化为它们的甲酯。情况。在这种光化学诱导的反应条件下，可以通过引入的保护三烷基甲硅烷基和所用的醇如MeOH和EtOH来调节和实现高度化学选择性的脱保护。
• REACTION OF STABLE TRIALKYLSILYL ESTERS WITH Ph₃P(SCN)₂: A NOVEL METHOD FOR THE PREPARATION OF ACYL AND AROYL ISOTHIOCYANATES UNDER NEUTRAL CONDITION
  作者：N. Iranpoor、H. Firouzabadi、H. R. Shaterian

  DOI：10.1081/scc-120014983

  日期：2002.1

  one-pot conversion of stable triisopropylsilyl- and tert-butyldimethylsilyl carboxylates to their corresponding acyl- or aroyl isothiocyanates using in-situ generation of Ph3P(SCN)2 at room temperature under neutral condition. This method has also been applied for the high yield preparation of 2-thioxo-3,4-dihydro-2H-1,3-benzoxazine-4-one, which has fungicidal and bactericidal activities.

  摘要描述了一种高效、温和且新颖的方法，可在中性条件下在室温下原位生成 Ph3P(SCN)2，将稳定的三异丙基甲硅烷基和叔丁基二甲基甲硅烷基羧酸酯一锅法转化为相应的酰基或芳酰基异硫氰酸酯。该方法还用于高产率制备具有杀菌和杀菌活性的2-thioxo-3,4-dihydro-2H-1,3-benzoxazine-4-one。
• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.
• AIZPURUA J. M.; COSSIO F. P.; PALOMO C., J. ORG. CHEM., 51,(1986) N 25, 4941-4943
  作者：AIZPURUA J. M.、 COSSIO F. P.、 PALOMO C.

  DOI：——

  日期：——