2-苯基-2-哌啶乙酸乙酯 | 7550-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-苯基-2-哌啶乙酸乙酯
• 英文名称: ethyl 2-phenyl-2-(piperidin-1-yl)acetate
• 英文别名: α-Piperidinophenylessigsaeureethylester；Ethyl 2-phenyl-2-piperidinoacetate；ethyl 2-phenyl-2-piperidin-1-ylacetate
• CAS: 7550-06-3
• 化学式: C₁₅H₂₁NO₂
• mdl: MFCD00445824
• 分子量: 247.337
• InChiKey: AGSKYKDXQOBAPX-UHFFFAOYSA-N

物化性质

• 沸点：
  148-149 °C(Press: 0.4 Torr)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-苯基-2-哌啶乙酸乙酯 在 盐酸 作用下， 生成 2-苯基-2-(哌啶-1-基)乙酸
  参考文献：
  名称：

  Wunderlich, Pharmazie, 1954, vol. 9, p. 15,17

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 苯乙酸乙酯 在 2,6-bis[(4,4-dimethyl)-2-oxazolin-2-yl]pyridine copper bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.17h， 以84%的产率得到2-苯基-2-哌啶乙酸乙酯
  参考文献：
  名称：

  Synthesis and characterization of bisoxazolines- and pybox-copper(ii) complexes and their application in the coupling of α-carbonyls with functionalized amines

  摘要：

  [Dm-Pybox)CuBr₂] 在催化酮和酯的α-氨基化反应中表现高效，对羰基和胺反应组分上的官能团具有较好的耐受性。

  DOI：

  10.1039/c4ob01027b

文献信息

• [EN] QUINUCLIDINE ESTERS OF 1-AZAHETEROCYCLYLACETIC ACID AS ANTIMUSCARINIC AGENTS, PROCESS FOR THEIR PREPARATION AND MEDICINAL COMPOSITIONS THEREOF<br/>[FR] ESTERS DE QUINUCLIDINE ET D'ACIDE 1-AZAHÉTÉROCYCLYLACÉTIQUE UTILISÉS COMME AGENTS ANTIMUSCARINIQUES, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS MÉDICINALES CORRESPONDANTES
  申请人：CHIESI FARMA SPA

  公开号：WO2013098145A1

  公开（公告）日：2013-07-04

  The invention relates to compounds of formula (I), wherein A, R1, R2, X, m and n are as defined in the specification, as selective M3 receptor antagonists, process for their preparation, composition comprising them and the therapeutic use thereof. Said compounds may be used in the treatment of, inter alia, a respiratory disease such as asthma and COPD.

  本发明涉及通式(I)的化合物，其中A、R1、R2、X、m和n如说明书中所定义，作为选择性M3受体拮抗剂，其制备方法，包含它们的组合物及其治疗用途。这些化合物可用于治疗，特别是呼吸系统疾病，如哮喘和慢性阻塞性肺病(COPD)。
• QUINUCLIDINE ESTERS OF 1-AZAHETEROCYCLYLACETIC ACID AS ANTIMUSCARINIC AGENTS, PROCESS FOR THEIR PREPARATION AND MEDICINAL COMPOSITIONS THEREOF
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US20130172302A1

  公开（公告）日：2013-07-04

  Compounds of formula (I): wherein A, R1, R2, X, m, and n are as defined in the specification, are selective M3 receptor antagonists and may be used in the treatment of, inter alia, a respiratory disease such as asthma and COPD.

  式(I)化合物： 其中A、R1、R2、X、m和n如说明书中所定义，是选择性的M3受体拮抗剂，可用于治疗，包括但不限于，呼吸系统疾病，如哮喘和慢性阻塞性肺病(COPD)。
• Ruthenium-Catalyzed One-Pot Carbenoid N−H Insertion Reactions and Diastereoselective Synthesis of Prolines
  作者：Qing-Hai Deng、Hai-Wei Xu、Angella Wing-Hoi Yuen、Zhen-Jiang Xu、Chi-Ming Che

  DOI：10.1021/ol800087p

  日期：2008.4.1

  3-hydroxyprolines and various other amino esters are conveniently prepared by [RuCl2(p-cymene)]2-catalyzed one-pot intramolecular and intermolecular carbenoid N-H insertion reactions, respectively, and the prolines are formed with high diastereoselectivities. The catalytic reactions are tolerant toward air/moisture, and the product yields are insensitive to the organic solvents used.

  芳基和脂族取代的3-羟基脯氨酸和各种其他氨基酸酯分别通过[RuCl2（p-cymene）] 2-催化的一锅分子内和分子间类胡萝卜素NH插入反应可方便地制备，且脯氨酸具有高非对映选择性。催化反应对空气/水分具有耐受性，并且产物收率对所用有机溶剂不敏感。
• Betrachtungen zur Herstellung von Methadon-nitril und Isomethadon-nitril sowie verwandten Verbindungen
  作者：B. Unterhalt、B. Coesfeld

  DOI：10.3797/scipharm.aut-00-21

  日期：——

  The 2-chloro-1-dialkylamino-propanes 4a-d are reacted with diphenylacetonitrile under phase transfer conditions to give a mixture of the nitriles 1a-d and 2a-d. Both chloro-dialkylamino-1-phenyl-ethanes 7a-d and 8a-d lead to 4-dialkylamino-2,2,3-triphenyl-butyronitriles 6a-d.

  使2-氯-1-二烷基氨基丙烷4a-d在相转移条件下与二苯基乙腈反应，得到腈1a-d和2a-d的混合物。氯-二烷基氨基-1-苯基乙烷7a-d和8a-d均导致4-二烷基氨基-2,2,3-三苯基-丁腈6a-d。
• Alpha, alpha-diphenyl-beta-amino-propanols
  申请人：HOECHST AG

  公开号：US02827460A1

  公开（公告）日：1958-03-18

  The invention comprises compounds of the general formula <;FORM:0816578/IV (b)/1>; in which R1 and R2 are each a hydrogen atom or a halogen atom or a hydroxyl, methyl, methoxy, ethoxy or benzyloxy group, and <;FORM:0816578/IV (b)/2>; represents a hydrogenated heterocyclic ring, and acid addition salts of these compounds. The compounds are made by the reaction of a phenyl magnesium halide with a phenyl ethyl ketone or a propionic acid ester, substituted in the side chain by a saturated heterocyclic radical, the phenyl radicals being substituted, if required, by halogen atoms or methyl, methoxy or ethoxy groups or benzyloxy groups and, if desired, splitting off the benzyl radical from any benzyloxy group in the product by catalytic hydrogenation. The bases obtained may be connected to their acid addition salts with, for example, hydrochloric, hydrobromic, hydriodic, sulphuric, phosphoric, amidosulphonic, formic, acetic, malonic, succinic, lactic, malic, maleic, citric, benzoic, salicylic, p-aminosalicylic, aceturic, phenol-sulphonic, hydroxyethane-sulphonic or ethylene diamine tetracetic acid. The compounds are used as therapeutic agents. Examples describe the preparation of the 1 : 1 - diphenyl - 2 - piperidino -, 1 - phenyl - 1 - (para - benzyloxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (para - hydroxyphenyl) - 2 - piperidino -, 1 : 1 - diphenyl - 2 - pyrrolidino -, 1 : 1 - diphenyl - 2 - morpholino -, 1 - phenyl - 1 - (4 - chlorophenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 : 4 - dimethoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 - ethoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (2 - methoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 - methylphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (4 - methoxyphenyl) - 2 - piperidino -, 1 : 1 - diphenyl - 2 - (1 : 2 : 3 : 4) - tetrahydro - isoquinolino - and 1 : 1 - diphenyl - 2 - (a - methyl - piperidino) - propanols. Phenyl ethyl ketones, substituted by a basic group in the a -position, which are used as starting materials, are made by treating a propiophenone with bromine and reacting the product with a heterocyclic base. Specified ketones prepared by this method comprise a -piperidinopropiophenone and the corresponding p-benzyloxy and m-p-dimethoxy derivatives, a -pyrrolidino - propiophenone a - morpholino - propiophenone, a - (1 : 2 : 3 : 4)tetrahydro - isoquinoline - propiophenone and a - (a 1 - methylpiperidino) - propiophenone. Specifications 307,304, 307,307, [both in Class 2 (iii)], and 491,951, [Group IV], are referred to.

  该发明包括一般公式<;FORM:0816578/IV (b)/1>;中的化合物，其中R1和R2分别是氢原子或卤素原子或羟基、甲基、甲氧基、乙氧基或苄氧基，<;FORM:0816578/IV (b)/2>;代表氢化杂环环，并且这些化合物的酸盐。这些化合物是通过苯基镁卤化物与苯基乙基酮或丙酸酯的反应制备的，该酮在侧链上被饱和杂环基取代，苯基基团在需要时被卤素原子或甲基、甲氧基、乙氧基或苄氧基取代，如有需要，通过催化氢化从任何苄氧基的苄基基团中将苄基基团剥离。所得到的碱可以与它们的酸盐连接，例如，盐酸、溴化氢、碘化氢、硫酸、磷酸、酰胺磺酸、甲酸、乙酸、丙二酸、琥珀酸、乳酸、苹果酸、马来酸、枸橼酸、苯甲酸、水杨酸、对氨基水杨酸、乙酰基尿素、酚磺酸、羟基乙烷磺酸或乙二胺四乙酸。这些化合物被用作治疗剂。示例描述了1:1-二苯基-2-哌啶基-、1-苯基-1-(对-苄氧基苯基)-2-哌啶基-、1-苯基-1-(对-羟基苯基)-2-哌啶基-、1:1-二苯基-2-吡咯啉基-、1:1-二苯基-2-吗啉基-、1-苯基-1-(4-氯苯基)-2-哌啶基-、1-苯基-1-(3:4-二甲氧基苯基)-2-哌啶基-、1-苯基-1-(3-乙氧基苯基)-2-哌啶基-、1-苯基-1-(2-甲氧基苯基)-2-哌啶基-、1-苯基-1-(3-甲基苯基)-2-哌啶基-、1-苯基-1-(4-甲氧基苯基)-2-哌啶基-、1:1-二苯基-2-(1:2:3:4)-四氢异喹啉基-和1:1-二苯基-2-(α-甲基-哌啶基)-丙醇的制备。作为起始物质使用的α-位置上带有碱性基团的苯乙酮是通过用溴处理丙酮制备的，然后将产物与杂环碱反应得到。通过这种方法制备的指定酮包括α-哌啶基丙酮及相应的对-苄氧基和间-p-二甲氧基衍生物、α-吡咯啉基-丙酮、α-吗啉基-丙酮、α-(1:2:3:4)四氢-异喹啉基-丙酮和α-(α-甲基哌啶基)-丙酮。参考规范307,304，307,307，[均属于第2类(III)], 和491,951，[IV组]。