ethyl 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate | 122846-56-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate
• 英文别名: ethyl 2-hydroxy-3-morpholino-2-phenylpropanoate；Ethyl 2-Hydroxy-2-phenyl-3-(4-morpholinyl)propionate；Ethyl 2-hydroxy-3-morpholin-4-yl-2-phenylpropanoate
• CAS: 122846-56-4
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: XABZIKXVCIWTRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate 在 sodium 作用下， 以 乙醚 为溶剂， 反应 43.0h， 生成 3-(1-methyl-1-azabicyclo<2.2.2>octyl) 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate iodide
  参考文献：
  名称：

  Synthesis of some 3-(1-azabicyclo[2.2.2]octyl) 3-amino-2-hydroxy-2-phenylpropionates: profile of antimuscarinic efficacy and selectivity

  摘要：

  A series of 3-quinuclidinyl atrolactate [3-(1-azabicyclo[2.2.2]octyl) 2-hydroxy-2-phenylpropionate, QNA] derivatives in which the methyl group of the parent is substituted with a tertiary amino substituent was prepared and tested for antimuscarinic activity. In general, potency was markedly decreased, although the morpholinyl and thiomorpholinyl derivatives retained significant activity. These compounds were also examined for muscarinic receptor subtype selectivity. Their subtype selectivities were comparable to that of (R,R)-QNA. The results of this investigation suggest possible differences in the accessory binding sites of the proteinaceous receptor subtypes.

  DOI：

  10.1021/jm00163a050
• 作为产物：
  描述：

  ethyl 2-methoxy-3-morpholino-2-phenylpropanoate 在 三氟化硼乙醚 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以52%的产率得到ethyl 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate
  参考文献：
  名称：

  钯催化的类胡萝卜素正式插入N，O-缩醛：直接获得α-烷氧基-β-氨基酸酯†

  摘要：

  通过在适度的反应条件下，钯催化将类胡萝卜素选择性地正式插入N，O-缩醛中，已开发出一种新的高效反应来合成α-烷氧基-β-氨基酸酯。广泛的具有不同取代基的α-重氮酯和各种N，O-缩醛均与该方案兼容，从而以良好或优异的收率提供了相应的α-烷氧基-β-氨基酸酯。

  DOI：

  10.1039/c9cc01374a

文献信息

• 1-azabicyclo[2.2.2]octan-3-yl 2-aryl-3-azacyclo-2-hydroxypropionates and
  申请人：Marion Laboratories, Inc.

  公开号：US04843074A1

  公开（公告）日：1989-06-27

  Novel 1-azabicyclo[2.2.2]octan-3-yl 2-aryl-3-azacyclo-2-hydroxypropionates and their quaternary salts and their use as antimuscarinic agents having antisecretory activity selective for the gastrointestinal tract are disclosed. The compounds have the formula: ##STR1## wherein: X=H, halogen, lower alkyl, lower alkoxy, hydroxy, and R=morpholinyl, thiomorpholinyl, piperidinyl, 1,4-dioxa-8-azaspiro[4.5]decanyl, 4-(2,6-dimethylmorpholinyl), 4-ketopiperidinyl, 4-hydroxypiperidinyl, 4-substituted piperazinyl (wherein the substituent is lower alkyl, hydroxyalkyl, acetoxyalkyl, or acyl). Also disclosed are pharmaceutical compositions for treatment of irritable bowel syndrome and methods for using such compounds.

  揭示了1-azabicyclo[2.2.2]辛烷-3-基2-芳基-3-氮杂环-2-羟基丙酸酯及其季铵盐，以及它们作为选择性针对胃肠道具有抗分泌活性的抗胆碱药物的用途。这些化合物具有以下结构式：##STR1##其中：X=H、卤素、较低的烷基、较低的烷氧基、羟基，R=吗啉基、硫代吗啉基、哌啶基、1,4-二氧-8-氮杂螺[4.5]癸基、4-(2,6-二甲基吗啉基)、4-酮哌啶基、4-羟基哌啶基、4-取代哌嗪基（其中取代基为较低的烷基、羟基烷基、乙酰氧基烷基或酰基）。还揭示了用于治疗肠易激综合征的药物组合物以及使用这些化合物的方法。
• RZESZOTARSKI, WACLAW J.;AUDIA, VICKI H.;WEITZBERG, MOSHE
  作者：RZESZOTARSKI, WACLAW J.、AUDIA, VICKI H.、WEITZBERG, MOSHE

  DOI：——

  日期：——
• US4843074A
  申请人：——

  公开号：US4843074A

  公开（公告）日：1989-06-27
• Palladium-catalyzed formal insertion of carbenoids into <i>N</i>,<i>O</i>-aminals: direct access to α-alkoxy-β-amino acid esters
  作者：Wenhui Wang、Hanmin Huang

  DOI：10.1039/c9cc01374a

  日期：——

  has been developed to synthesize α-alkoxy-β-amino acid esters via palladium-catalyzed selective formal insertion of carbenoids into N,O-aminals under mild reaction conditions. A broad range of α-diazoesters with different substituents and various N,O-aminals were compatible with this protocol, affording the corresponding α-alkoxy-β-amino acid esters in good to excellent yields.

  通过在适度的反应条件下，钯催化将类胡萝卜素选择性地正式插入N，O-缩醛中，已开发出一种新的高效反应来合成α-烷氧基-β-氨基酸酯。广泛的具有不同取代基的α-重氮酯和各种N，O-缩醛均与该方案兼容，从而以良好或优异的收率提供了相应的α-烷氧基-β-氨基酸酯。
• Synthesis of some 3-(1-azabicyclo[2.2.2]octyl) 3-amino-2-hydroxy-2-phenylpropionates: profile of antimuscarinic efficacy and selectivity
  作者：Vicki H. Audia、Daniel W. McPherson、Moshe Weitzberg、W. Janusz Rzeszotarski、Bonnie Sturm、James F. Kachur、Mary Abreu、Carl Kaiser

  DOI：10.1021/jm00163a050

  日期：1990.1

  A series of 3-quinuclidinyl atrolactate [3-(1-azabicyclo[2.2.2]octyl) 2-hydroxy-2-phenylpropionate, QNA] derivatives in which the methyl group of the parent is substituted with a tertiary amino substituent was prepared and tested for antimuscarinic activity. In general, potency was markedly decreased, although the morpholinyl and thiomorpholinyl derivatives retained significant activity. These compounds were also examined for muscarinic receptor subtype selectivity. Their subtype selectivities were comparable to that of (R,R)-QNA. The results of this investigation suggest possible differences in the accessory binding sites of the proteinaceous receptor subtypes.