2-<(tert-butyldimethylsilyl)methyl>-3-phenylpropanoic acid methyl ester | 137685-80-4

• 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: 2-<(tert-butyldimethylsilyl)methyl>-3-phenylpropanoic acid methyl ester
• 英文别名: methyl 3-phenyl-2-(tert-butyldimethylsilyloxymethyl)propanoate；methyl 2-benzyl-3-(t-butyldimethylsilyloxy)-propionate；Methyl 2-benzyl-3-(t-butyldimethylsilyloxy)propionate；methyl 2-benzyl-3-[tert-butyl(dimethyl)silyl]oxypropanoate
• CAS: 137685-80-4
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: HPGLBDDLLKCZAW-UHFFFAOYSA-N

物化性质

• 沸点：
  345.6±30.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(tert-butyldimethylsilyl)methyl>-3-phenylpropanoic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以68%的产率得到3-(t-butyldimethylsilyl)oxy-2-benzyl-propanoic acid
  参考文献：
  名称：

  具有C8手性取代基的黄嘌呤作为有效的和选择性的腺苷A1拮抗剂。

  摘要：

  合成了几种8-取代的1,3-二丙基黄嘌呤，并测量了它们在腺苷A1和A2受体上的受体结合亲和力。当检查化合物的对映异构体对时，R对映异构体比相应的S对映异构体显着更有效。在A1受体上最有效的化合物是（R）-3,7-二氢-8-（1-甲基-2-苯乙基）-1,3-二丙基-1H-嘌呤-2,6-di one（5a; MDL 102,503），其在A1受体处的Ki值为6.9 nM。但是，更具选择性的化合物是（R）-3,7-二氢-8-（1-苯丙基）-1,3-二丙基-1H-嘌呤-2,6-二酮（5d； MDL 102,234）， A1受体的Ki值为23.2 nM，A2 / A1的比率为153。

  DOI：

  10.1021/jm00077a004
• 作为产物：
  描述：

  2-benzyl-3-hydroxypropanoic acid 在 咪唑 、 三甲基氯硅烷 作用下， 反应 16.5h， 生成 2-<(tert-butyldimethylsilyl)methyl>-3-phenylpropanoic acid methyl ester
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Trans Peptide Isostere Based on the Bioactive Conformations of Saquinavir and Nelfinavir

  摘要：

  The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R:5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.

  DOI：

  10.1021/jo0016834

文献信息

• Xanthine derivatives as adenosine A1 receptor antagonists
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05840729A1

  公开（公告）日：1998-11-24

  A method of attenuating a cognitive deficit in a patient in need thereof comprising administering to the patient a xanthine derivative.

  一种减轻患者认知缺陷的方法，包括向患者施用黄嘌呤衍生物。
• Selective adenosine receptor agents
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05047534A1

  公开（公告）日：1991-09-10

  Xanthine derivative which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectively and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which will enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.

  本发明揭示了在腺苷受体上选择性作用的黄嘌呤衍生物，通常作为腺苷拮抗剂。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外的腺苷受体活性与体内的腺苷受体活性相关。根据本文披露的化合物的选择性结合活性，可以制备这些化合物的药物制剂，这将增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。
• Design and Synthesis of a Conformationally Restricted Trans Peptide Isostere Based on the Bioactive Conformations of Saquinavir and Nelfinavir
  作者：Michael K. Edmonds、Andrew D. Abell

  DOI：10.1021/jo0016834

  日期：2001.6.1

  The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R:5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.
• Xanthines with C8 chiral substituents as potent and selective adenosine A1 antagonists
  作者：Norton P. Peet、Nelsen L. Lentz、Mark W. Dudley、Ann Marie L. Ogden、Deborah R. McCarty、Margaret M. Racke

  DOI：10.1021/jm00077a004

  日期：1993.12

  Several 8-substituted 1,3-dipropylxanthines were synthesized, and their receptor binding affinities at adenosine A1 and A2 receptors were measured. When enantiomeric pairs of compounds were examined, the R enantiomers were significantly more potent than the corresponding S enantiomers. The most potent compound at the A1 receptor was (R)-3,7-dihydro-8-(1-methyl-2-phenylethyl)-1,3-dipropyl-1H-purine-2,6-di

  合成了几种8-取代的1,3-二丙基黄嘌呤，并测量了它们在腺苷A1和A2受体上的受体结合亲和力。当检查化合物的对映异构体对时，R对映异构体比相应的S对映异构体显着更有效。在A1受体上最有效的化合物是（R）-3,7-二氢-8-（1-甲基-2-苯乙基）-1,3-二丙基-1H-嘌呤-2,6-di one（5a; MDL 102,503），其在A1受体处的Ki值为6.9 nM。但是，更具选择性的化合物是（R）-3,7-二氢-8-（1-苯丙基）-1,3-二丙基-1H-嘌呤-2,6-二酮（5d； MDL 102,234）， A1受体的Ki值为23.2 nM，A2 / A1的比率为153。