2-tert-butyldimethylsilyloxy-2-phenylethanoic acid | 849937-09-3

• 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: 2-tert-butyldimethylsilyloxy-2-phenylethanoic acid
• 英文别名: O-TBS-mandelic acid；2-[Tert-butyl(dimethyl)silyl]oxy-2-phenylacetic acid
• CAS: 849937-09-3
• 化学式: C₁₄H₂₂O₃Si
• 分子量: 266.412
• InChiKey: AAOUHSHTMZETQC-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C(Solv: dichloromethane (75-09-2); ethyl ether (60-29-7))
• 沸点：
  327.9±30.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  18
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tert-butyldimethylsilyloxy-2-phenylethanoic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 30.0h， 生成 1,3,4,6,7,8,9,9a-octahydro-3-(tert-butyldimethylsilyloxy)-3-phenyl-2H-quinolizine
  参考文献：
  名称：

  Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement

  摘要：

  This paper describes the synthesis of functionalised azecine and azonine derivatives incorporating the adrenaline motif. In a key step, an enolate assisted aza Claisen rearrangement was employed to interconvert from 6- and 5-membered heterocycles to their corresponding 10- and 9-membered lactams. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.061
• 作为产物：
  描述：

  扁桃酸 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 2-tert-butyldimethylsilyloxy-2-phenylethanoic acid
  参考文献：
  名称：

  Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement

  摘要：

  This paper describes the synthesis of functionalised azecine and azonine derivatives incorporating the adrenaline motif. In a key step, an enolate assisted aza Claisen rearrangement was employed to interconvert from 6- and 5-membered heterocycles to their corresponding 10- and 9-membered lactams. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.061

文献信息

• PIDA-Mediated Rearrangement for the Synthesis of Enantiopure Triazolopyridinones
  作者：Zenghui Ye、Hong Zhang、Na Chen、Yanqi Wu、Fengzhi Zhang

  DOI：10.1021/acs.orglett.0c02278

  日期：2020.8.21

  oxidative cyclization/1,2-carbon migration of hydrazides for the synthesis of otherwise inaccessible hindered or enantiopure triazolopyridinones has been developed. This protocol exhibits broad substrate scope and can be easily scaled up by continuous flow synthesis under mild conditions. Most importantly, this method demonstrates a rearrangement with retention of configuration and can be readily applied

  已经开发了酰肼的串联氧化环化/ 1,2-碳迁移，用于合成否则无法获得的受阻或对映纯三唑并吡啶并酮。该方案具有广泛的底物范围，可以通过在温和条件下进行连续流合成轻松地扩大规模。最重要的是，该方法显示了重排并保留了构型，可以很容易地应用于含羧酸的药物，氨基酸和天然产物的后期修饰，以得到对映纯的三唑并吡啶并酮。
• A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
  作者：Christian Eidamshaus、Roopender Kumar、Mrinal K Bera、Hans-Ulrich Reissig

  DOI：10.3762/bjoc.7.108

  日期：——

  reaction of alkoxyallenes, nitriles and carboxylic acids to provide beta-methoxy-beta-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described

  描述了在 2 位和 6 位具有立体侧链的高度官能化 4-羟基吡啶衍生物的实用方法。所提出的两步法利用烷氧基丙二烯、腈和羧酸的多组分反应来提供 β-甲氧基-β-酮烯酰胺，其在随后的环缩合反应中转化为 4-羟基吡啶。该过程显示出广泛的底物范围，并以良好到中等的产率产生差异取代的对映体纯吡啶。描述了多种取代乳酸衍生的 pyrid-4-yl nonaflates 的制备。提供了多组分反应的假定机制的其他证据。
• Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-sulfonic acid derivatives.
  作者：TAISUKE MATSUO、TOHRU SUGAWARA、HIROTOMO MASUYA、YASUHIKO KAWANO、NORIYOSHI NOGUCHI、MICHIHIKO OCHIAI

  DOI：10.1248/cpb.31.1874

  日期：——

  Sulfazecin (1) is a monocyclic β-lactam antibiotic isolated from strain G-6302, Pseudomonas acidophila. As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-2-azetidinone (16) was synthesized from penicillins, and various new compounds were synthesized by acylation and sulfonation of 16. Some of these new compounds showed potent antibacterial activity.

  磺胺嘧啶（1）是从嗜酸性假单胞菌 G-6302 菌株中分离出来的一种单环 β-内酰胺类抗生素。作为合成磺胺嘧啶衍生物的关键中间体，3-氨基-2-氮杂环丁酮（16）是由青霉素类化合物合成的。其中一些新化合物具有很强的抗菌活性。
• Unusual lability of α-silyloxy β-amino carboxylic acid derivatives
  作者：Michael N. Greco、H.Marlon Zhong、Bruce E. Maryanoff

  DOI：10.1016/s0040-4039(98)00967-8

  日期：1998.7

  Saponification and mild acidification of alpha-silyloxy homo-arginine derivative 2c revealed an unusual lability of the silyl protecting group. A systematic study of related substrates indicates that hydrogen bonding between the alpha-amino hydrogen and the carbonyl oxygen is critical for facile desilylation. A mechanism involving neighboring group participation of NH and carboxyl groups is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• HOFMANN, UTE;HOLZER, SABINE;MEESE, CLAUS O., J. CHROMATOGR., 508,(1990) N, C. 349-356
  作者：HOFMANN, UTE、HOLZER, SABINE、MEESE, CLAUS O.

  DOI：——

  日期：——