2-(diethylamino)ethyl 2-methyl-2-phenyl-3-chloropropanoate | 129780-01-4

• 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: 2-(diethylamino)ethyl 2-methyl-2-phenyl-3-chloropropanoate
• 英文别名: 2-(Diethylamino)ethyl 3-chloro-2-methyl-2-phenylpropanoate
• CAS: 129780-01-4
• 化学式: C₁₆H₂₄ClNO₂
• 分子量: 297.825
• InChiKey: HNFMQMJPKNONAU-UHFFFAOYSA-N

物化性质

• 沸点：
  387.9±27.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(diethylamino)ethyl 2-methyl-2-phenyl-3-chloropropanoate 在 二环己烷并-18-冠醚-6 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 288.0h， 以99%的产率得到2-(Diethylamino)ethyl 3-iodo-2-methyl-2-phenylpropanoate
  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 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 27.5h， 生成 2-(diethylamino)ethyl 2-methyl-2-phenyl-3-chloropropanoate
  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.