1,1-二乙氧基-1-[乙氧基(乙基)磷基]乙烷 | 23081-61-0

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦酸及其衍生物
• 中文名称: 1,1-二乙氧基-1-[乙氧基(乙基)磷基]乙烷
• 英文名称: ethyl 1,1-diethoxyethyl(ethyl)phosphinate
• 英文别名: Ethyl-(1,1-diethoxy-ethyl)-phosphinsaeure-ethylester；Phosphinic acid, (1,1-diethoxyethyl)ethyl-, ethyl ester；1,1-diethoxy-1-[ethoxy(ethyl)phosphoryl]ethane
• CAS: 23081-61-0
• 化学式: C₁₀H₂₃O₄P
• 分子量: 238.264
• InChiKey: NKCATCXIVXDKLA-UHFFFAOYSA-N

物化性质

• 沸点：
  128-129 °C(Press: 12 Torr)
• 密度：
  1.0180 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 1,1-二乙氧基-1-[乙氧基(乙基)磷基]乙烷 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 ethyl ethylphosphinate
  参考文献：
  名称：

  Phosphinic Acid Analogs of GABA. 2. Selective, Orally Active GABAB Antagonists

  摘要：

  In 1987, 25 years after the synthesis of the potent and selective GABA(B) agonist baclofen (1), Kerr et al.(5) described the first GABA(B) antagonist phaclofen 2. However, phaclofen and structurally similar derivatives 3-5 did not cross the blood-brain barrier and hence were inactive in vivo as central nervous system agents. As a consequence, the therapeutic potential of GABA(B) antagonists remained unclear. In exploring GABA and baclofen derivatives by replacing the carboxylic acid residue with various phosphinic acid groups, we discovered more potent and water soluble GABA(B) antagonists. Electrophysiological experiments in vivo demonstrated that some of the new compounds were capable of penetrating the blood-brain barrier after oral administration. Neurotransmitter release experiments showed that they interacted with several presynaptic GABA(B) receptor subtypes, enhancing the release of GABA, glutamate, aspartate, and somatostatin. The new GABA(B) antagonists interacted also with postsynaptic GABA(B) receptors, as they blocked late inhibitory postsynaptic potentials. They facilitated the induction of long-term potentiation in vitro and in, vivo, suggesting potential cognition enhancing effects. Fifteen compounds were investigated in Various memory and learning paradigms in rodents. Although several compounds were found to be active, only 10 reversed the age-related deficits of old rats in a multiple-trial one-way active avoidance test after chronic treatment. The cognition facilitating effects of 10 were confirmed in learning experiments in Rhesus monkeys. The novel GABA(B) antagonists showed also protective effects in various animal models of absence epilepsy.

  DOI：

  10.1021/jm00017a016
• 作为产物：
  描述：

  溴乙烷 、 ethyl (1,1-diethoxyethyl)phosphinate 以 四氢呋喃 、 水 为溶剂， 生成 1,1-二乙氧基-1-[乙氧基(乙基)磷基]乙烷
  参考文献：
  名称：

  Substituted propane-phosphinic acid compounds

  摘要：

  公式I的化合物##STR1##其中R表示具有2个或更多碳原子的脂肪族、环脂族、环脂族-脂肪族或芳基脂肪基，其中R.sup.1、R.sup.2和R.sup.3中的一个代表氢或脂肪族、环脂族、芳基脂肪基或芳香族基，R.sup.1、R.sup.2和R.sup.3中的另一个是氢或在R.sup.1和R.sup.2的情况下是羟基，而R.sup.1、R.sup.2和R.sup.3中的剩余一个是氢，或者R表示甲基，R.sub.1表示氢或羟基，R.sub.2表示芳基，R.sub.3表示氢，它们的盐具有GABA.sub.B-拮抗性质，可用作GABA.sub.B-拮抗剂。当在公式II的化合物中获得它们##STR2##其中R、R.sup.1、R.sup.2和R.sup.3具有其先前的含义，Z表示--NH.sub.2，R.sup.4表示羟基保护基R.sup.5或者当R.sup.1和R.sup.3表示氢且R.sup.2表示氢或烷基时，表示碱金属或铵离子R.sup.6，或者Z表示受保护或潜在的氨基Z.sup.0且R.sup.4表示氢或羟基保护基R.sup.5，任何一个R.sup.5或R.sup.6基团被氢取代，和/或任何一个Z.sup.0基团被转化为--NH.sub.2。

  公开号：

  US05064819A1

文献信息

• Neurologically-Active Compounds
  申请人：Chebib Mary

  公开号：US20080032950A1

  公开（公告）日：2008-02-07

  The invention provides a compound of the formula I: wherein R is methyl, ethyl, propyl, isopropyl, butyl, pentyl, neo-pentyl or cyclohexyl, or a salt or solvate thereof. These compounds are selective GABA C receptor antagonists. The invention also provides pharmaceutical compositions comprising a compound of formula I or a pharmaceutically acceptable salt or solvate thereof. The invention also provides methods of enhancing the cognitive activity of an animal and methods of stimulating memory capacity in an animal, comprising the step of administering to the animal an effective amount of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof.

  本发明提供一种化合物，其化学式为I：其中R为甲基、乙基、丙基、异丙基、丁基、戊基、新戊基或环己基，或其盐或溶剂化物。这些化合物是选择性的GABAC受体拮抗剂。本发明还提供包括化合物I或其药学上可接受的盐或溶剂化物的制药组合物。本发明还提供增强动物认知活动和刺激动物记忆能力的方法，其中包括向动物施用化合物I或其药学上可接受的盐或溶剂化物的有效量。
• Moskva,V.V. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 563 - 566
  作者：Moskva,V.V. et al.

  DOI：——

  日期：——
• NEUROLOGICALLY-ACTIVE COMPOUNDS
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：EP1773740B1

  公开（公告）日：2009-02-18
• US5013863A
  申请人：——

  公开号：US5013863A

  公开（公告）日：1991-05-07
• US5051524A
  申请人：——

  公开号：US5051524A

  公开（公告）日：1991-09-24