(R)-3-甲基哌啶 | 16078-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (R)-3-甲基哌啶
• 英文名称: (R)-3-methylpiperidine
• 英文别名: (3R)-3-methylpiperidine；3-methylpiperidine
• CAS: 16078-25-4
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: JEGMWWXJUXDNJN-ZCFIWIBFSA-N

物化性质

• 沸点：
  125℃
• 密度：
  0.809
• 闪点：
  17℃
• 保留指数：
  829

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-3-甲基哌啶 生成 4-(3-methylpiperidino)tetrahydro-2H-thiopyran-4-carbonitrile
  参考文献：
  名称：

  Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same

  摘要：

  这项发明涉及具有选择性亲和力的新型苯环丙胺衍生物，以及用于制备它们的方法、含有它们的药物组合物，以及它们作为中枢或外周神经系统细胞的保护剂对抗急性或慢性退化，或作为抗癫痫药物的用途。

  公开号：

  US06342511B1
• 作为产物：
  描述：

  1,5-二氨基-2-甲基戊烷 在 R-selective imine reductase from streptosporangium roseum 、 NAD⁺-reducing hydrogenase from Ralstonia eutropha H₁₆, variant E₃₄₁A/S₃₄₂R 、 putrescine oxidase from Rhodococcus erythropolis, variant E₂₀₃G 、 水 、 氢气 、 氧气 、 还原型辅酶II(NADPH)四钠盐 、 catalase 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 以22%的产率得到(R)-3-甲基哌啶
  参考文献：
  名称：

  在O 2的存在下，通过H 2驱动的NADPH循环，由二胺合成N-杂环

  摘要：

  在本文中，我们报道了一种酶级联反应，其中涉及用于H 2驱动的N-杂环合成的氧化酶，亚胺还原酶和氢化酶。鉴定了来自红球红球菌的腐胺氧化酶具有改善的活性的变体。一锅反应中直接从相应的二胺底物中获得了高达97％的产物生成取代的吡咯烷和哌啶。高达93％ee的形成使我们深入了解了腐胺氧化酶的特异性和选择性。

  DOI：

  10.1039/c8gc03798a

文献信息

• SUBSTITUTED BIPIPERIDINYL DERIVATIVES
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US20160318866A1

  公开（公告）日：2016-11-03

  The invention relates to novel substituted bipiperidinyl derivatives, to processes for their preparation, to their use for the treatment and/or prevention of diseases and to their use for preparing medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of diabetic microangiopathies, diabetic ulcers on the extremities, in particular for promoting wound healing of diabetic foot ulcers, diabetic heart failure, diabetic coronary microvascular heart disorders, peripheral and cardiac vascular disorders, thromboembolic disorders and ischaemias, peripheral circulatory disturbances, Raynaud's phenomenon, CREST syndrome, microcirculatory disturbances, intermittent claudication, and peripheral and autonomous neuropathies.

  该发明涉及新型取代的双哌啶衍生物，涉及它们的制备方法，涉及它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防糖尿病微血管病变、四肢糖尿病溃疡，特别是促进糖尿病足溃疡愈合、糖尿病心力衰竭、糖尿病冠状微血管心脏疾病、外周和心脏血管疾病、血栓栓塞疾病和缺血、外周循环障碍、雷诺现象、CREST综合征、微循环障碍、间歇性跛行以及外周和自主神经病变的治疗和/或预防。
• Kinetic resolution of amines with enantiopure 3-N,N-diacylaminoquinazolin-4(3H)-ones
  作者：Al-Sehemi, Abdullah G.、Atkinson, Robert S.、Fawcett, John

  DOI：10.1039/b105917n

  日期：2002.1.7

  The title compounds (DAQs) are chiral when the two N-acyl groups are different because of the absence of rotation around the N–N bond (a chiral axis). Enantiopure DAQs have been obtained by incorporation of a chiral centre in enantiopure form either into the substituent at the Q2-position or into one of the N-acyl groups, or into both, followed by separation of diastereoisomers. This separation is unnecessary in one case because conversion of the N-monoacylaminoquinazolinone (MAQ) into the DAQ is completely diastereoselective. Neither is separation of diastereoisomers necessary with 3-[N,N-di-(S)-2-acetoxypropanoylamino]-2-diphenylmethylquinazolin-4(3H)-one 37a: this DAQ 37a has its N–N bond rendered a chiral axis by the bias in its imide moiety wholly in favour of one exo/endo conformation.The high chemoselectivity exhibited by N,N-diacetyl- or N,N-dibenzoylaminoquinazolinones in reaction with the less hindered of two secondary amines (pyrrolidine in the presence of 1 eq. of piperidine) has a stereoselective counterpart: reaction of the above enantiopure DAQs enantioselectively with racemic amines leading to kinetic resolution. Using 1 eq. of DAQ and 2 eq. of amine, both the derivatised and unreacted amine enantiomers are recovered with high enantiomeric excess (ee) (better than 90% ee in some cases). Some of the higher ees are found in the recovered amides where non-chemoselective attack on both N-acyl groups of the DAQ has occurred: from the opposite configurations of the amine component in the two amides and from the low enantiopurity of the recovered unreacted amine, reaction of each of the N-acyl groups with complementary enantiomers of the amine is occurring (parallel kinetic resolution).Although higher ees are, in general, obtained using secondary amines, high ees are obtained in some cases using 1-phenylethylamine and, in particular, amino acid esters (valine and alanine).The sense of enantioselectivity in the reactions of these DAQs with amines is controlled by the configuration of the N–N axis: replacing the Q group in an N-(S)-2-acetoxypropanoyl-N-acetyl-bearing DAQ by phthalimide, thus eliminating the N–N chiral axis, drastically reduces the level of kinetic resolution.

  标题化合物(DAQs)在两个N-酰基团不同时是手性的，因为N-N键（一个手性轴）缺乏旋转。通过将手性中心以手性形式引入Q2-位点的取代基或其中一个N-酰基团，或两者中，随后分离diastereoisomers，得到了纯对映体的DAQs。在一个情况下，这种分离是不必要的，因为将N-单酰胺基喹唑啉酮(MAQ)转化为DAQ是完全立体选择性的。对于3-[N,N-di-(S)-2-乙酰氧基丙酰胺基]-2-二苯甲基喹唑啉-4(3H)-酮37a，也不需要分离diastereoisomers：这个DAQ 37a通过其亚胺部分的偏向完全倾向于一个exo/endo构象，使其N-N键成为一个手性轴。N,N-二乙酰基或N,N-二苯甲酰氨基喹唑啉酮在与两个次级胺中较少受到阻碍的胺（在存在1 eq.的哌啶的情况下使用吡咯烷）反应时表现出高度的化学选择性，这在立体选择性上有对应：上述纯对映体的DAQs与外消旋胺反应，导致动力学拆分。使用1 eq.的DAQ和2 eq.的胺，衍生化的和未反应的胺对映体都以高对映体过量（ee）回收（在一些情况下优于90% ee）。在一些回收的酰胺中发现较高的ee，其中非化学选择性地攻击DAQ的两个N-酰基团：从两个酰胺中胺组分的相反构型和回收的未反应胺的低对映纯度，每个N-酰基团与胺的互补对映体反应（并行动态拆分）。尽管通常使用次级胺得到较高的ee，但在某些情况下使用1-苯乙胺，特别是氨基酸酯（缬氨酸和丙氨酸）得到高ee。这些DAQs与胺反应的对映选择性的方向受N-N轴配置的控制：在带有N-(S)-2-乙酰氧基丙酰基-N-乙酰基的DAQ中，通过用邻苯二甲酰亚胺替换Q组，从而消除N-N手性轴，显著降低了动力学拆分的水平。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：MEDICAL RES COUNCIL TECHNOLOGY

  公开号：WO2010106333A1

  公开（公告）日：2010-09-23

  A compound of formula (I), or a pharmaceutically acceptable salt or ester thereof, wherein R1 is selected from: aryl; heteroaryl; -NHR3; fused aryl-C4-7-heterocycloalkyI; -CONR4R5; -NHCOR6; -C3-7-cycloalkyl; -O-C3-7-cycloalkyl; -NR3R6; and optionally substituted -C1-6 alkyl; wherein said aryl, heteroaryl, fused aryl-C4-7-heterocycloalkyl and C4-7-heterocycloalkyl are each optionally substituted; R2 is selected from hydrogen, aryl, C1-6-alkyl, C2-6-alkenyl, C3-7-cycloalkyl, heteroaryl, C4-7 heterocycloalkyl and halogen, wherein said C1-6-alkyl, C2-6-alkenyl, aryl, heteroaryl and C4-7-heterocycloalkyl are each optionally substituted. Further aspects relate to pharmaceutical compositions, therapeutic uses and process for preparing compounds of formula (I).

  一种具有式（I）的化合物，或其药学上可接受的盐或酯，其中R1选自：芳基；杂环芳基；-NHR3；融合芳基-C4-7-杂环烷基；-CONR4R5；-NHCOR6；-C3-7-环烷基；-O-C3-7-环烷基；-NR3R6；和可选择地取代的-C1-6烷基；其中所述的芳基、杂环芳基、融合芳基-C4-7-杂环烷基和C4-7-杂环烷基均可选择地取代；R2选自氢、芳基、C1-6-烷基、C2-6-烯基、C3-7-环烷基、杂环芳基、C4-7-杂环烷基和卤素，其中所述的C1-6-烷基、C2-6-烯基、芳基、杂环芳基和C4-7-杂环烷基均可选择地取代。进一步涉及制备具有式（I）的化合物的药物组合物、治疗用途和制备方法的其他方面。
• [EN] INHIBITORS OF ADRENORECEPTOR ADRAC2<br/>[FR] INHIBITEURS DE L'ADRÉNORÉCEPTEUR ADRAC2
  申请人：BAYER AG

  公开号：WO2021089683A1

  公开（公告）日：2021-05-14

  The present application relates to novel substituted heterocyclic carboxamides, to processes for their preparation, to their use alone or in combinations for the treatment and/or prevention of diseases and to their use for producing medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of breathing difficulties including sleep-induced breathing difficulties such as central and obstructive sleep apnoea, snoring (primary and obstructive snoring), dysphagia, peripheral and cardiac vascular disorders including diabetic microangiopathies and disorders of the peripheral and central nervous system including neurodegenerative and neuroinflammatory disorders.

  本申请涉及新型取代杂环羧酰胺，其制备方法，它们单独或组合用于治疗和/或预防疾病以及用于生产用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防呼吸困难，包括睡眠引起的呼吸困难，如中枢性和阻塞性睡眠呼吸暂停、打鼾（原发性和阻塞性打鼾）、吞咽困难、周围和心脏血管疾病，包括糖尿病微血管病变和周围和中枢神经系统疾病，包括神经退行性和神经炎症性疾病。
• First Direct Synthesis of Optically Active 3-Methylcyclopentene
  作者：Hans-Richard Silwka、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19840670212

  日期：1984.3.14

  (−)-(S)- and (+)-(R)-3-methylcyclopentene (1) has been prepared in a stereochemically unambiguous synthesis. The (S)-configuration for (−)-1 was confirmed by correlation with (−)-(S)-1-methylindane.

  （-）-（S）-和（+）-（R）-3-甲基环戊烯（1）已经通过立体化学明确的合成方法制备。通过与（-）-（S）-1-甲基茚满的相关性确认了（-）- 1的（S）构型。