(-)-2-(diethylamino)ethyl α-methyltropate | 99545-92-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (-)-2-(diethylamino)ethyl α-methyltropate
• 英文别名: 2-(Diethylamino)ethyl 3-hydroxy-2-methyl-2-phenylpropanoate
• CAS: 99545-92-3
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: FZIBGNNMMCDSHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-2-(diethylamino)ethyl α-methyltropate 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 5.0h， 以94.5%的产率得到2-(diethylamino)ethyl 2-methyl-2-phenyl-3-(tosyloxy)propanoate
  参考文献：
  名称：

  Molecular modification of anticholinergics as probes for muscarinic receptors. 2. Amino esters of .alpha.-methyltropic acid

  摘要：

  As a continuation of our goals to study molecular probes for muscarinic cholinergic receptors, a series of 3-substituted 2-methyl-2-phenylpropanoates with the general structure of C6H5C(CH2X)(CH3)COOCH2CH2NEt2 where X = OH, OTs, F, Cl, Br, I, and OAc were prepared and their antispasmodic activities examined on isolated rat ileum preparations. Structure-activity relationship studies with these compounds provide further evidence suggesting that binding of an aromatic moiety in a specific location within the hydrophobic region of the receptor is important for anticholinergic potency. A nucleophilic displacement of chloride by "naked" fluoride under mild conditions is also reported.

  DOI：

  10.1021/jm00385a028
• 作为产物：
  描述：

  2-苯基-2-(羟甲基)丙酸乙酯 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 10.5h， 生成 (-)-2-(diethylamino)ethyl α-methyltropate
  参考文献：
  名称：

  Molecular modification of anticholinergics as probes for muscarinic receptors. 2. Amino esters of .alpha.-methyltropic acid

  摘要：

  As a continuation of our goals to study molecular probes for muscarinic cholinergic receptors, a series of 3-substituted 2-methyl-2-phenylpropanoates with the general structure of C6H5C(CH2X)(CH3)COOCH2CH2NEt2 where X = OH, OTs, F, Cl, Br, I, and OAc were prepared and their antispasmodic activities examined on isolated rat ileum preparations. Structure-activity relationship studies with these compounds provide further evidence suggesting that binding of an aromatic moiety in a specific location within the hydrophobic region of the receptor is important for anticholinergic potency. A nucleophilic displacement of chloride by "naked" fluoride under mild conditions is also reported.

  DOI：

  10.1021/jm00385a028

文献信息

• LU M. C.; SHIH L. B.; JAE H. S.; GEARIEN J. E.; THOMPSON E. B., J. MED. CHEM., 30,(1987) N 2, 424-427
  作者：LU M. C.、 SHIH L. B.、 JAE H. S.、 GEARIEN J. E.、 THOMPSON E. B.

  DOI：——

  日期：——
• Molecular modification of anticholinergics as probes for muscarinic receptors. 2. Amino esters of .alpha.-methyltropic acid
  作者：Matthias C. Lu、Lisa B. Shih、Hwan S. Jae、James E. Gearien、Emmanual B. Thompson

  DOI：10.1021/jm00385a028

  日期：1987.2

  As a continuation of our goals to study molecular probes for muscarinic cholinergic receptors, a series of 3-substituted 2-methyl-2-phenylpropanoates with the general structure of C6H5C(CH2X)(CH3)COOCH2CH2NEt2 where X = OH, OTs, F, Cl, Br, I, and OAc were prepared and their antispasmodic activities examined on isolated rat ileum preparations. Structure-activity relationship studies with these compounds provide further evidence suggesting that binding of an aromatic moiety in a specific location within the hydrophobic region of the receptor is important for anticholinergic potency. A nucleophilic displacement of chloride by "naked" fluoride under mild conditions is also reported.