(2R)-2-(4-t-butylbenzyl)-3-hydroxypropyl pivalate | 1003002-91-2

• 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: (2R)-2-(4-t-butylbenzyl)-3-hydroxypropyl pivalate
• 英文别名: [(2R)-2-[(4-tert-butylphenyl)methyl]-3-hydroxypropyl] 2,2-dimethylpropanoate
• CAS: 1003002-91-2
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: HZYSNMJNNFLNJM-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  (2R)-2-(4-t-butylbenzyl)-3-hydroxypropyl pivalate 在 二苯基膦叠氮化物 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到(2R)-3-azido-2-(4-t-butylbenzyl)propyl pivalate
  参考文献：
  名称：

  Stereospecific High-affinity TRPV1 Antagonists: Chiral N-(2-Benzyl-3-pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide Analogues

  摘要：

  Previously, we reported the thiourea antagonists 2a and 2b as potent and high affinity TRPV1 antagonists. For further optimization of the lead compounds, a series of their amide and alpha-substituted amide surrogates were investigated and novel chiral N-(2-benzyl-3-pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide analogues were characterized as potent and stereospecific rTRPV1 antagonists. In particular, compounds 72 and 73 displayed high binding affinities, with K-i values of 4.12 and 1.83 nM and potent antagonism with Ki values of 0.58 and 5.2 nM, respectively, in rTRPV1/CHO cells. These values are comparable or more potent than those of 5-iodoRTX under the same assay conditions. A distinctive binding model that includes two hydrophobic pockets is proposed for this series of compounds based on docking studies of 57 and 72 with a homology model of the TM3/4 region of TRPV1.

  DOI：

  10.1021/jm701049p
• 作为产物：
  描述：

  (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(4-t-butylphenyl)-1-propanol 在 吡啶 、 sodium tetrahydroborate 、 高碘酸 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (2R)-2-(4-t-butylbenzyl)-3-hydroxypropyl pivalate
  参考文献：
  名称：

  α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists

  摘要：

  A series of alpha-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of alpha-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.054