(2S)-(-)-1-(3',4'-dibenzyloxyphenoxy)-3-(2-(3'',4''-dimethoxyphenyl)ethylamino)-2-propanol | 782436-39-9

• 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: (2S)-(-)-1-(3',4'-dibenzyloxyphenoxy)-3-(2-(3'',4''-dimethoxyphenyl)ethylamino)-2-propanol
• 英文别名: (2S)-1-(3',4'-dibenzyloxyphenoxy)-3-(3',4'-dimethoxyphenyl)ethylamino-2-propanol；(S)-1-(3,4-Bis(benzyloxy)phenoxy)-3-((3,4-dimethoxyphenethyl)amino)propan-2-ol；(2S)-1-[3,4-bis(phenylmethoxy)phenoxy]-3-[2-(3,4-dimethoxyphenyl)ethylamino]propan-2-ol
• CAS: 782436-39-9
• 化学式: C₃₃H₃₇NO₆
• 分子量: 543.66
• InChiKey: MUJQUOGOAXEIKS-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-(-)-1-(3',4'-dibenzyloxyphenoxy)-3-(2-(3'',4''-dimethoxyphenyl)ethylamino)-2-propanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 10.0h， 生成 (2S)-1-(3,4-dihydroxyphenoxy)-3-[2-(3',4'-dimethoxyphenyl)ethyl]amino-2-propanol
  参考文献：
  名称：

  Asymmetric Synthesis of (2S)‐1‐(3,4‐Dihydroxyphenoxy)‐3‐(3,′4′‐Dimethoxyphenoxy) Ethylamino‐2‐propanol hydrochloride (RO363)

  摘要：

  Enantiomerically pure (S)-RO363 was synthesized by using (R,R) Salen Co(III) complex for the resolution of terminal epoxide. The hydrolytic kinetic resolution process was carried out at room temperature in excellent enantioselectivity. The method can be applied for large-scale preparation of (S)RO363.

  DOI：

  10.1080/00397910600602651
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (2S)-(-)-1-(3',4'-dibenzyloxyphenoxy)-3-(2-(3'',4''-dimethoxyphenyl)ethylamino)-2-propanol
  参考文献：
  名称：

  Synthesis and β-adrenoceptor agonist properties of (±)-1-(3',4'-dihydroxyphenoxy)-3-(3",4"-dimethoxyphenyl) ethylamino-2-propanol hydrochloride, (±)-RO363.HCl, and the (2S)-(-)-isomer

  摘要：

  The synthesis of (+/-)-1-(3 ',4'-dihydroxyphenoxy)-3-(3",4"-dimethoxyphenyl)ethylamino-2-propanol hydrochloride, (+/-)R0363.HCl, and the (2S)-(-)-isomer is described for the first time. The binding affinities for (+/-)-R0363.HCl, (2S)-(-)-R0363.HCl and a number of well known beta-adrenoceptor agonists for transfected human beta(1)-, beta(2)-and beta(3),-adrenoceptors expressed in Chinese hamster ovary cells have been determined and compared with the functional potencies in rat atria (beta(1)) and trachea (beta(2)). The results indicate that both (+/-)-R0363 and (2S)-(-)-R0363 are selective for the human and rat beta(1)-adrenoceptors. The (2S)-(-)-isomer of R0363, as expected, has a higher binding affinity for the human and functional potency for rat beta-adrenoceptor subtypes than the racemate. However, in contrast to the catecholamines and formoterol, the functional potency of the racemic mixture and its (-)-enantiomer are not significantly different from their binding affinity, suggesting that they are examples of partial agonists with sufficient intrinsic activity to produce full agonist responses. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80103-2