cis-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine | 31138-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
• 英文别名: 2-ethylidene-1,5-dimethyl-3,3-diphenyl-pyrrolidine；2-Aethyliden-1,5-dimethyl-3,3-diphenyl-pyrrolidin；(+/-)-2-Aethyliden-1,5-dimethyl-3,3-diphenyl-pyrrolidin；(+/-)-2-Ethyliden-1,5-dimethyl-3,3-diphenyl-pyrrolidin；2-Ethyliden-1,5-dimethyl-3,3-diphenylpyrrolidin；2-Ethylidin-l,5-dimethyl-3,3-diphenylpyrrolidin；2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine；(2Z)-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
• CAS: 31138-77-9
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: AJRJPORIQGYFMT-PVOVUMCXSA-N

物化性质

• 沸点：
  393.9±42.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)
• 碰撞截面：
  166.2 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]
• 保留指数：
  2040.5

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 、 草酸 生成 5-ethyl-1,2-dimethyl-4,4-diphenyl-2,3-dihydropyrrol-1-ium;2-hydroxy-2-oxoacetate
  参考文献：
  名称：

  BECKETT A. H.; ESSIEN E. E.; ANTIRI-PENROSE C., J. PHARM. AND PHARMACOL., 1975, 27, NO 7, 497-501

  摘要：

  DOI：
• 作为产物：
  描述：

  methadone N-oxide 生成 cis-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
  参考文献：
  名称：

  BECKETT A. H.; ESSIEN E. E.; ANTIRI-PENROSE C., J. PHARM. AND PHARMACOL., 1975, 27, NO 7, 497-501

  摘要：

  DOI：

文献信息

• Structural preferences for the double bond position in some unsaturated 3,3-diphenylpyrrolidines
  作者：M. M. A. Hassan、A. F. Casy

  DOI：10.1139/v70-625

  日期：1970.12.1

  The reaction between 3,3-diphenyl-3-cyano-1-methylpropyl isocyanate and ethyl magnesium bromide leads to 2-ethyl-5-methyl-3,3-diphenyl-1-pyrroline rather than the isomeric 2-ethylidenepyrrolidine. The protonated N-methyl analogue (identical with a major metabolite of methadone) retains the 1-pyrroline structure, but the free base is a cis-trans mixture of the corresponding 2-ethylidenepyrrolidines; the cis Me/Ph isomer preponderates and is the sole product (obtained as a quaternary salt) when the mixture is treated with methyl iodide. 5-Methyl-2-methylene-3,3-diphenylpyrrolidine, a lower homologue of the methadone metabolite, isomerizes to a 1-pyrroline derivative when protonated or methylated. All structural conclusions are based on i.r. and p.m.r. spectroscopic evidence.

  3,3-二苯基-3-氰基-1-甲基丙基异氰酸酯与溴化乙基镁的反应导致2-乙基-5-甲基-3,3-二苯基-1-吡咯烯，而不是同分异构体2-乙基亚丙基吡咯啉。质子化的N-甲基类似物（与美沙酮的一个主要代谢物相同）保留了1-吡咯烯结构，但游离碱是相应的2-乙基亚丙基吡咯啉的顺反异构体混合物；顺式Me/Ph异构体占优势，并且在用甲基碘处理混合物时是唯一的产物（以季铵盐形式获得）。5-甲基-2-亚甲基-3,3-二苯基吡咯啉，是美沙酮代谢物的较低同系物，在质子化或甲基化时异构化为1-吡咯烯衍生物。所有结构性结论均基于红外光谱和质子磁共振光谱证据。
• COMPOSITIONS AND METHODS FOR DETECTION OF METHADONE METABOLITE
  申请人：Lele Bhalchandra

  公开号：US20130203076A1

  公开（公告）日：2013-08-08

  Methods and reagents are disclosed for conducting assays for EDDP. The reagents include a moiety selected from the group consisting of poly(amino acid) label moieties, non-poly(amino acid) label moieties, poly(amino acid) immunogenic carriers, non-poly(amino acid) immunogenic carriers, non-label poly(amino acid) moieties, and non-immunogenic carrier poly(amino acid) moieties linked to 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine at the 3-position of one of the phenyl rings. Antibodies produced from immunogenic EDDP conjugates and labeled EDDP conjugates are employed in assays for determining the presence and/or amount of EDDP in samples suspected of containing EDDP.

  本文披露了用于进行EDDP检测的方法和试剂。试剂包括从聚（氨基酸）标记基团、非聚（氨基酸）标记基团、聚（氨基酸）免疫载体、非聚（氨基酸）免疫载体、非标记聚（氨基酸）基团和非免疫载体聚（氨基酸）基团中选择的基团，这些基团与2-乙基亚乙烯-1,5-二甲基-3,3-二苯基吡咯烷在其中一个苯环的3位链接。从免疫原性EDDP共轭物和标记的EDDP共轭物中产生的抗体被用于检测样本中可能含有EDDP的存在和/或量。
• [EN] 2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE ANALOGS AND METHODS FOR THEIR SYNTHESIS AND USE<br/>[FR] ANALOGUES DE 2-ÉTHYLIDÈNE-1,5-DIMÉTHYL-3,3-DIPHÉNYLPYRROLIDINE ET PROCÉDÉS POUR LEUR SYNTHÈSE ET UTILISATION
  申请人：ALERE SAN DIEGO INC

  公开号：WO2017201314A1

  公开（公告）日：2017-11-23

  The present invention relates to novel 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine analogs, and methods for their synthesis and use. Such analogs are designed to provide a convenient linkage chemistry for coupling under mild conditions to a suitable group on a target protein, polypeptide, solid phase or detectable label.

  本发明涉及新型2-乙烯基-1,5-二甲基-3,3-二苯基吡咯烷类似物，以及它们的合成和使用方法。这些类似物旨在为耦合到目标蛋白质、多肽、固相或可检测标记的适当基团提供方便的连接化学，在温和条件下进行耦合。
• Methadone fluorescence polarization immunoassay
  申请人：ABBOTT LABORATORIES

  公开号：EP0380019A2

  公开（公告）日：1990-08-01

  A fluorescence polarization immunoassay for detecting the presence of methadone in a test sample is provided, based upon competition between methadone and a fluorescently labeled tracer for the binding sites on an antibody specific for methadone. The concentration of methadone in the sample determines the amount of tracer that binds to the antibody. The amount of tracer-antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of methadone in the sample. Tracers used as reagents and immunogens used to raise antibodies for use as reagents are also disclosed.

  根据美沙酮和荧光标记示踪剂对美沙酮特异性抗体上结合位点的竞争，提供了一种荧光偏振免疫测定法，用于检测测试样品中是否含有美沙酮。样品中美沙酮的浓度决定了与抗体结合的示踪剂的量。形成的示踪剂-抗体复合物的量可以定量测量，并与样本中的美沙酮量成反比。此外，还公开了用作试剂的示踪剂和用于培养抗体以用作试剂的免疫原。
• Immunogens for raising antibodies useful in methadone fluorescence polarization immunoassay
  申请人：ABBOTT LABORATORIES

  公开号：EP0662613A1

  公开（公告）日：1995-07-12

  An immunogen useful in eliciting antibodies for determining the presence or amount of methadone in a test sample, comprising the structure: wherein:    R and R' represent a spacer group consisting of from 0 to 15 carbon atoms and heteroatoms, including not more than six heteroatoms, arranged in a straight or branched chain, saturated or unsaturated, with the proviso that not more than two heteroatoms may be linked in sequence and, in the case of R, that branchings may occur only on carbon atoms;    x is 0 or 1;    M is a linking group selected from C=O, -NH-, O-C=O, N-C=O, and N-C=S; and    Q is an immunogenic carrier. Haptens used to make the immunogens are also disclosed.

  一种用于激发抗体以确定测试样品中是否存在美沙酮或其含量的免疫原，包括以下结构： 其中 R和R'代表由0至15个碳原子和杂原子（包括不超过6个杂原子）组成的间隔基团，排列成饱和或不饱和的直链或支链，但不得有两个以上的杂原子依次相连，在R的情况下，只能在碳原子上发生分支； x 为 0 或 1； M 是一个连接基团，选自 C=O、-NH-、O-C=O、N-C=O 和 N-C=S；以及 Q 是免疫原载体。用于制造免疫原的巯基也已公开。