tert-butyldimethylsilyl 2-phenylethanoate | 78323-99-6

• 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: tert-butyldimethylsilyl 2-phenylethanoate
• 英文别名: tert-Butyl(dimethyl)silyl phenylacetate；[tert-butyl(dimethyl)silyl] 2-phenylacetate
• CAS: 78323-99-6
• 化学式: C₁₄H₂₂O₂Si
• 分子量: 250.413
• InChiKey: LISQZGMJTHVNMI-UHFFFAOYSA-N

物化性质

• 沸点：
  283.3±19.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)
• 保留指数：
  1494

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  tert-butyldimethylsilyl 2-phenylethanoate 、 二溴三苯基膦 以 二氯甲烷 为溶剂， 生成 2-苯基乙酰溴
  参考文献：
  名称：

  Reagents and synthetic methods. 61. Reaction of hindered trialkylsilyl esters and trialkylsilyl ethers with triphenylphosphine dibromide: preparation of carboxylic acid bromides and alkyl bromides under mild neutral conditions

  摘要：

  DOI：

  10.1021/jo00375a034
• 作为产物：
  描述：

  苯乙酸 、 叔丁基二甲基哇烷基咪唑 生成 tert-butyldimethylsilyl 2-phenylethanoate
  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

• Methylenations of heteroatom-substituted carbonyls with dimethyl titanocene
  作者：Nicos A. Petasis、Shao-Po Lu

  DOI：10.1016/0040-4039(95)00320-c

  日期：1995.4

  Reaction of dimethyl titanocene with a variety of heteroatom-substituted carbonyl compounds, including: silylesters, anhydrides, carbonates, amides, imides, thioesters, selenoesters and acyl silanes gives the corresponding heteroatom-substituted alkenes.

  二甲基钛茂与多种杂原子取代的羰基化合物反应，包括：甲硅烷基酯，酸酐，碳酸盐，酰胺，酰亚胺，硫代酸酯，硒酸酯和酰基硅烷，得到相应的杂原子取代的烯烃。
• 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。
• KIM, KYOUNG R.;HAHN, MI K.;ZLATKIS, ALBERT;HORNING, EVAN C.;MIDDLEDITCH, +, J. CHROMATOGR., 460,(1989) C. 289-301
  作者：KIM, KYOUNG R.、HAHN, MI K.、ZLATKIS, ALBERT、HORNING, EVAN C.、MIDDLEDITCH, +

  DOI：——

  日期：——
• 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：——

表征谱图