(R)-2-(4-(tert-butyl)benzyl)-3-(3-(3-methoxy-4-(methoxymethoxy)benzyl)thioureido)propyl pivalate | 1528740-82-0

• 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: (R)-2-(4-(tert-butyl)benzyl)-3-(3-(3-methoxy-4-(methoxymethoxy)benzyl)thioureido)propyl pivalate
• CAS: 1528740-82-0
• 化学式: C₃₀H₄₄N₂O₅S
• 分子量: 544.756
• InChiKey: SZNCEBAYGIRDMB-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78.05
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-(tert-butyl)benzyl)-3-(3-(3-methoxy-4-(methoxymethoxy)benzyl)thioureido)propyl pivalate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到[(2R)-2-[(4-tert-butylphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methylcarbamothioylamino]propyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands

  摘要：

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.064
• 作为产物：
  描述：

  Tert-butyl N-[(2R)-2-[(4-tert-butylphenyl)methyl]-3-hydroxypropyl]carbamate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (R)-2-(4-(tert-butyl)benzyl)-3-(3-(3-methoxy-4-(methoxymethoxy)benzyl)thioureido)propyl pivalate
  参考文献：
  名称：

  Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands

  摘要：

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.064