ethyl butylphosphinate | 21661-52-9

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: ethyl butylphosphinate
• 英文别名: ethyl (n-butyl)phosphinate；ethyl butyl-H-phosphinate；ethyl n-butylphosphinate；butyl-phosphinic acid ethyl ester；Butyl-phosphinsaeure-aethylester；ethyl n-butylhydrogenophosphinate；1-Ethoxyphosphonoylbutane
• CAS: 21661-52-9
• 化学式: C₆H₁₅O₂P
• 分子量: 150.158
• InChiKey: VHFXTWLRIPRLKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl butylphosphinate 在 镍 氨 、 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 10.0~75.0 ℃ 、10.0 MPa 条件下， 反应 5.0h， 生成 ethyl (3-aminopropyl)-n-butylphosphinate
  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：

  氯甲酸乙酯 、 n-butylphosphinic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到ethyl butylphosphinate
  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

文献信息

• Substituted propane-phosphinic acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US05064819A1

  公开（公告）日：1991-11-12

  Compounds of the formula I ##STR1## wherein R denotes an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical having 2 or more carbon atoms, and wherein one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen or, in the case of R.sup.1 and R.sup.2, is hydroxy, and the remaining one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen, or wherein R denotes methyl, R.sub.1 denotes hydrogen or hydroxy, R.sub.2 denotes an aromatic radical and R.sub.3 represents hydrogen, and their salts have GABA.sub.B -antagonistic properties and can be used as GABA.sub.B -antagonists. They are obtained when in a compound of formula II ##STR2## in which R, R.sup.1, R.sup.2 and R.sup.3 have their previous significances, Z represents --NH.sub.2 and R.sup.4 denotes a hydroxy-protective group R.sup.5 or, when R.sup.1 and R.sup.3 denote hydrogen and R.sup.2 denotes hydrogen or alkyl, denotes an alkali metal or ammonium ion R.sup.6, or Z represents a protected or latent amino group Z.sup.0 and R.sup.4 denotes hydrogen or a hydroxy-protective group R.sup.5, any group R.sup.5 or R.sup.6 is replaced by hydrogen, and/or any group Z.sup.0 is converted into --NH.sub.2.

  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。
• P-subsituted propane-phosphinic acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US05190934A1

  公开（公告）日：1993-03-02

  Compounds of the formula I ##STR1## wherein either R.sub.1 is halogen, R.sub.1 ' is halogen or hydrogen and R.sub.2 and R.sub.2 ' denote hydrogen or R.sub.1 and R.sub.1 ' represent hydrogen, R.sub.2 is an aliphatic or aromatic radical and R.sub.2 ' is hydroxy or R.sub.2 and R.sub.2 ' together represent oxo, and wherein R denotes an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical having 2 or more carbon atoms or, if R.sub.1 and R.sub.1 ' denote hydrogen, R.sub.2 represents an aromatic radical and R.sub.2 ' is hydroxy, R represents methyl, and their salts are useful as nootropics, antidepressants and/or anxiolytics. The can be manufacture by replacing any group R.sub.5 by hydrogen and/or converting any group Z.sub.0 into amino in a compound of formula II ##STR2## in which R, R.sub.1, R.sub.1 ', R.sub.2 and R.sub.2 ' have their previous significances, Z represents a protected or latent amino group Z.sub.0 and R.sub.4 denotes hydrogen or a hyddroxy-protective group R.sub.5, and wherein amino as a constituent of R and/or hydroxy R.sub.2 ' or oxo R.sub.2 +R.sub.2 ' may be present in a temporarily protected form.

  式I的化合物##STR1##中，R.sub.1为卤素，R.sub.1'为卤素或氢，R.sub.2和R.sub.2'表示氢或R.sub.1和R.sub.1'代表氢，R.sub.2为脂肪族或芳香基团，R.sub.2'为羟基或R.sub.2和R.sub.2'一起表示羰基，其中R表示具有2个或更多碳原子的脂肪族、环脂肪族、环脂肪族-脂肪族或芳基脂肪族基团，或者如果R.sub.1和R.sub.1'表示氢，则R.sub.2表示芳香基团，R.sub.2'为羟基，R表示甲基，它们的盐可用作脑功能增强剂、抗抑郁剂和/或抗焦虑剂。可以通过将任何基团R.sub.5替换为氢和/或将任何基团Z.sub.0转化为氨基来制备，其中R、R.sub.1、R.sub.1'、R.sub.2和R.sub.2'具有其先前的含义，Z表示受保护或潜在的氨基团Z.sub.0，R.sub.4表示氢或羟基保护基团R.sub.5，氨基作为R的组分和/或羟基R.sub.2'或羰基R.sub.2+R.sub.2'可能以暂时受保护的形式存在于式II的化合物中##STR2##。
• [EN] NEW PHOSPHORUS CONTAINING HETEROCYCLIC COMPOUNDS, SUGAR ANALOGUES, AND COMPOSITIONS HAVING ANTI-CANCER ACTIVITY CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES CONTENANT DU PHOSPHORE, ANALOGUES DE SUCRES, ET COMPOSITIONS AYANT UNE ACTIVITÉ ANTICANCÉREUSE LES CONTENANT
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2009004096A1

  公开（公告）日：2009-01-08

  The invention provides new anticancer compounds of formula (1) such as defined in the present description. The invention also provides pharmaceutical compositions to be used in human or veterinary medicine, comprising at least one compound of formula (1). The present invention further relates to a compound of formula (1) such as defined in the present description, for use as a drug. The invention further relates to the use of a compound of formula (1) for manufacturing a human or animal anticancer pharmaceutical composition.

  该发明提供了新的抗癌化合物，其化学式为（1），如本说明中所定义。该发明还提供了用于人类或兽医药物的制剂，包括至少一种化合物（1）。本发明进一步涉及一种化合物，其化学式为（1），如本说明中所定义，用作药物。该发明还涉及使用化合物（1）制造人类或动物抗癌药物组合物。
• Direct Monoalkylation of Alkyl Phosphinates to Access H-Phosphinic Acid Esters
  作者：Jean-Luc Montchamp、Isabelle Abrunhosa-Thomas、Patrice Ribière、Alicia C. Adcock

  DOI：10.1055/s-2005-924768

  日期：——

  Simple alkyl phosphinates prepared by the silicate esterification method can be alkylated under Barbier-like conditions with butyl lithium at -78 °C followed by warming to room temperature. The method is limited to the more reactive electrophile such as allylic bromides and alkyl iodides. With these electrophiles good yields of H-phosphinic acid esters are generally obtained in a straightforward manner

  通过硅酸酯化方法制备的简单烷基次膦酸盐可以在类似巴比尔的条件下与丁基锂在 -78 °C 下烷基化，然后升温至室温。该方法仅限于反应性更强的亲电子试剂，例如烯丙基溴化物和烷基碘化物。使用这些亲电子试剂，通常以简单的方式获得高产率的 H-次膦酸酯。
• Selective Hydrogenation Catalyst and Methods of Making and Using Same
  申请人：Cheung Tin-Tack Peter

  公开号：US20100228065A1

  公开（公告）日：2010-09-09

  A composition comprising a supported hydrogenation catalyst comprising palladium and an organophosphorous compound, the supported hydrogenation catalyst being capable of selectively hydrogenating highly unsaturated hydrocarbons to unsaturated hydrocarbons. A method of making a selective hydrogenation catalyst comprising contacting a support with a palladium-containing compound to form a palladium supported composition, contacting the palladium supported composition with an organophosphorus compound to form a catalyst precursor, and reducing the catalyst precursor to form the catalyst. A method of selectively hydrogenating highly unsaturated hydrocarbons to an unsaturated hydrocarbon enriched composition comprising contacting a supported catalyst comprising palladium and an organophosphorous compound with a feed comprising highly unsaturated hydrocarbon under conditions suitable for hydrogenating at least a portion of the highly unsaturated hydrocarbon feed to form the unsaturated hydrocarbon enriched composition.

  一种包括支持的氢化催化剂的组合物，其中氢化催化剂包括钯和有机磷化合物，支持的氢化催化剂能够选择性地将高度不饱和烃氢化为不饱和烃。一种制备选择性氢化催化剂的方法，包括将支持物与含钯化合物接触以形成支持的钯组合物，将支持的钯组合物与有机磷化合物接触以形成催化剂前体，并还原催化剂前体以形成催化剂。一种将高度不饱和烃选择性氢化为富含不饱和烃的组合物的方法，包括将包括钯和有机磷化合物的支持催化剂与含高度不饱和烃的进料接触，在适宜的氢化条件下至少部分氢化高度不饱和烃进料以形成富含不饱和烃的组合物。