ethyl (Z)-4-(9H-xanthen-9-yl)but-2-enoate | 403694-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl (Z)-4-(9H-xanthen-9-yl)but-2-enoate
• CAS: 403694-99-5
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: QEOQBGZLFVBKGI-QPEQYQDCSA-N

物化性质

• 沸点：
  399.5±21.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-4-(9H-xanthen-9-yl)but-2-enoate 在 草酰氯 、 bis(N-tert-butylsalicylaldiminato)copper(II) 、 三甲基铝 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二甲基苯胺 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-((R)-2-Hydroxy-1-phenyl-ethylamino)-[(1S,2S,3R)-2-(morpholine-4-carbonyl)-3-(9H-xanthen-9-ylmethyl)-cyclopropyl]-acetonitrile
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of novel 3′-Substituted carboxycyclopropylglycines as antagonists at group 2 metabotropic glutamate receptors

  摘要：

  Two novel 3'-substituted carboxycylopropylglycines, (2S,1'S,2'S,3'R)-2-(3'- xanthenylmethyl-2'-carboxycyclopropyl)glycine (8a) and (2S,1'S,2'S,3'R)-2-(3'-xanthenylethyl-2'-carboxycyclopropyl)glycine (8b), were synthesized and evaluated as mGluR ligands. Compound 8b showed to be a potent group II antagonist with submicromolar activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00656-4
• 作为产物：
  描述：

  2-(9H-xanthen-9-yl)acetaldehyde 、 bis(trifluoroethyl)phosphonoacetate ethyl ester 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到ethyl (Z)-4-(9H-xanthen-9-yl)but-2-enoate
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of novel 3′-Substituted carboxycyclopropylglycines as antagonists at group 2 metabotropic glutamate receptors

  摘要：

  Two novel 3'-substituted carboxycylopropylglycines, (2S,1'S,2'S,3'R)-2-(3'- xanthenylmethyl-2'-carboxycyclopropyl)glycine (8a) and (2S,1'S,2'S,3'R)-2-(3'-xanthenylethyl-2'-carboxycyclopropyl)glycine (8b), were synthesized and evaluated as mGluR ligands. Compound 8b showed to be a potent group II antagonist with submicromolar activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00656-4

文献信息

• Design, synthesis and preliminary evaluation of novel 3′-Substituted carboxycyclopropylglycines as antagonists at group 2 metabotropic glutamate receptors
  作者：Roberto Pellicciari、Gabriele Costantino、Maura Marinozzi、Antonio Macchiarulo、Laura Amori、Peter Josef Flor、Fabrizio Gasparini、Rainer Kuhn、Stephan Urwyler

  DOI：10.1016/s0960-894x(01)00656-4

  日期：2001.12

  Two novel 3'-substituted carboxycylopropylglycines, (2S,1'S,2'S,3'R)-2-(3'- xanthenylmethyl-2'-carboxycyclopropyl)glycine (8a) and (2S,1'S,2'S,3'R)-2-(3'-xanthenylethyl-2'-carboxycyclopropyl)glycine (8b), were synthesized and evaluated as mGluR ligands. Compound 8b showed to be a potent group II antagonist with submicromolar activity. (C) 2001 Elsevier Science Ltd. All rights reserved.