(R)-(-)-2-phenyl-2-piperidinoethanol | 154472-05-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-(-)-2-phenyl-2-piperidinoethanol
• 英文别名: (R)-2-phenyl-2-(piperidin-1-yl)ethanol；(2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol；2-phenyl-2-piperidin-1-yl-ethanol；(R)-2-phenyl-2-(piperidin-1-yl)ethan-1-ol；(R)-2-piperidino-2-phenylethanol；(2R)-2-phenyl-2-piperidin-1-ylethanol
• CAS: 154472-05-6
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: WBDNHYWAUADMHW-ZDUSSCGKSA-N

物化性质

• 沸点：
  317.1±22.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-phenyl-2-piperidinoethanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 16.5h， 以79%的产率得到(S)-1-(2-chloro-2-phenylethyl)piperidin-1-ium chloride
  参考文献：
  名称：

  羧酸对常见 N,N-二烷基氮丙啶鎓离子的高区域选择性开环

  摘要：

  DOI：

  10.3987/com-17-13770
• 作为产物：
  描述：

  左旋苯甘氨酸 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 异丙醇 、 xylene 为溶剂， 反应 5.0h， 生成 (R)-(-)-2-phenyl-2-piperidinoethanol
  参考文献：
  名称：

  Dehydrierung cyclischer tertiärer Amine unter Reaktionsbeteiligung von enantiomeren nucleophilen Nachbargruppen / Dehydrogenation of Cyclic Tertiary Amines with Neighbouring of Enantiomeric Nucleophiles

  摘要：

  为了对它们的脱氢进行立体化学研究，氨基醇1、2和3的对映体是从光学活性源制备而来的，而二胺8和9的对映体则通过分离外消旋体获得。化合物1、2和3的纯对映体通过邻近醇基的中间参与，通过汞(II)-EDTA的双重脱氢反应生成了光学活性内酰胺5、6和7，保持构型完全不变。同样地，通过四电子提取生成了环酰胺10和11的二胺8和9。

  DOI：

  10.1515/znb-2002-0409

文献信息

• Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
  作者：Maria Rosaria Acocella、Luciana D'Urso、Mario Maggio、Gaetano Guerra

  DOI：10.1002/cctc.201600241

  日期：2016.6.7

  The ring‐opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high‐surface‐area graphite and graphene oxide under metal‐free and solvent‐free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide

  在无金属和无溶剂条件下，高表面积的石墨和氧化石墨烯可有效地和区域选择性地催化环氧化物与胺的开环反应。对于不具有芳基的环氧化物，仅对氧化石墨烯观察到催化活性，因此，该活性必须归因于其酸性基团。相反，对于氧化苯乙烯，石墨和氧化石墨烯表现出相当相似的催化活性，因此，活性主要是由于与石墨π系统的π堆积相互作用而使亲电子环氧化物活化。所描述的氨解过程是绿色且廉价的，因为催化剂可以被回收和再循环而不损失效率。而且，
• Hydroxamic acid anesthetic compounds
  申请人：Pfizer Inc.

  公开号：US05837717A1

  公开（公告）日：1998-11-17

  A compound of the following formula: ##STR1## and its pharmaceutically acceptable salt thereof, wherein R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, phenyl or phenyl-C.sub.1-4 alkyl; or R.sup.1 and R.sup.2 are taken together with the nitrogen to which they are attached and form optionally substituted, saturated or unsaturated 3-, 4-, 5-, 6- or 7-membered heterocyclic cantaining one to two heteroatoms, provided that the heterocyclic is not pyrrolidinyl; R.sup.3 is hydrogen, C.sub.1-4 alkyl or a hydroxy protecting group; Ar is phenyl optionally substituted with one or more substituents selected from halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxy-C.sub.1-4 alkyloxy, CF.sub.3 and carboxy-C.sub.1-4 alkyloxy; and X is phenyl, naphthyl, biphenyl, indanyl, benzofuranyl, benzothiophenyl, 1-tetralone-6-yl, C.sub.1-4 alkylenedioxy, pyridyl, furyl or thienyl, these groups being optionally substituted with up to three substituents. These compounds and pharmaceutical compositions containing them are useful as analgesic, antiinflammatory, diuretic, antitussive, anesthetic or neuroprotective agents, or an agent for treatment of functional bowel disease such as abdominal pain, for the treatment of a mammalian subject, especially a human subject.

  以下式的化合物：##STR1##及其药用可接受的盐，其中R.sup.1和R.sup.2独立地为氢、C.sub.1-4烷基、C.sub.3-7环烷基、C.sub.2-4烯基、C.sub.1-4烷氧基、C.sub.1-4烷硫基、苯基或苯基-C.sub.1-4烷基；或者R.sup.1和R.sup.2与它们连接的氮一起取代，并形成可选择取代的饱和或不饱和的含有一到两个杂原子的3、4、5、6或7元杂环，前提是这种杂环不是吡咯烷基；R.sup.3为氢、C.sub.1-4烷基或羟基保护基；Ar为苯基，可选择地取代为来自卤素、羟基、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.1-4烷氧基-C.sub.1-4烷氧基、CF.sub.3和羧基-C.sub.1-4烷氧基的一个或多个取代基；X为苯基、萘基、联苯基、茚基、苯并呋喃基、苯并噻吩基、1-四氢基-6-基、C.sub.1-4烷二氧基、吡啶基、呋喃基或噻吩基，这些基可选择地取代为多达三个取代基。这些化合物和含有它们的药物组合物可用作镇痛、抗炎、利尿、止咳、麻醉或神经保护剂，或者用作治疗腹痛等功能性肠道疾病的药物，用于治疗哺乳动物受体，特别是人类受体。
• Thiyl Radical Mediated Racemization of Benzylic Amines
  作者：Stéphanie Escoubet、Stéphane Gastaldi、Nicolas Vanthuyne、Gérard Gil、Didier Siri、Michèle P. Bertrand

  DOI：10.1002/ejoc.200600120

  日期：2006.7

  Thiyl radical mediated reversible H abstraction from the stereogenic center α to the nitrogen atom is a mild method to racemize benzylic amines. Owing to the sensitivity of atom-transfer reactions to enthalpic effects, a knowledge of both the S–H and the α-C–H bond dissociation energies is fundamental to select the thiol that is appropriate to abstract the hydrogen atom from a given amine. In the absence

  硫基自由基介导的从立体中心 α 到氮原子的可逆 H 提取是一种使苄胺外消旋的温和方法。由于原子转移反应对焓效应的敏感性，了解 S-H 和 α-C-H 键解离能是选择适合从给定胺中提取氢原子的硫醇的基础。在缺乏实验数据的情况下，理论计算提供了一种有用的预测工具。此处描述的实验有助于描述在化学计量或催化量的硫醇存在下外消旋化在合理时间内进行必须满足的最佳条件。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• 1,4-dihydropyridines from dithionite reduction of pyridinium salts without electron-withdrawing groups as substituents
  作者：Yung-Sing Wong、Christian Marazano、Dino Gnecco、Bhupesh C. Das

  DOI：10.1016/s0040-4039(00)75796-0

  日期：1994.1

  Conditions have been established for the sodium dithionite (Na2S2O4) reduction of pyridinium salts 1 lacking electron-withdrawing substituents to their corresponding 1,4-dihydropyridines (1,4-DHPs) 2, a reaction which was previously reported to fail. The importance of hydrophobic effects for this reduction to take place could be recognized from the results obtained. The present procedure offers a very

  已经建立了亚硫酸钠（Na 2 S 2 O 4）还原没有吸电子取代基的吡啶鎓盐1到其相应的1,4-二氢吡啶（1,4-DHPs）2的条件，该反应先前被报道为失败。从获得的结果可以认识到疏水作用对于这种减少发生的重要性。本方法提供了通往许多1，4-DHP 2，特别是一系列手性衍生物如5和9的非常方便的途径。
• Hydroxamic acid compounds as opioid kappa receptor agonists
  申请人：PFIZER INC.

  公开号：EP0789021A1

  公开（公告）日：1997-08-13

  A compound of the following formula: and its pharmaceutically acceptable salt thereof, wherein R1 and R2 are independently hydrogen, C1-4 alkyl, C3-7 cycloalkyl, C2-4 alkenyl, C1-4 alkoxy-C1-4 alkyl, C1-4 alkylthio-C1-4 alkyl, phenyl, phenyl-C1-4alkyl, halo-substituted C1-4 alkyl, C3-7 cycloalkyl-C1-3 alkyl or hydroxy-C1-4alkyl ; or R1 and R2 are taken together with the nitrogen to which they are attached and form optionally substituted, saturated or unsaturated 3-, 4-, 5-, 6- or 7- membered heterocyclic cantaining one to two heteroatoms, provided that the heterocyclic is not pyrrolidinyl; R3 ishydrogen, C1-4 alkyl or a hydroxy protecting group; Ar isoptionally substituted phenyl or phenyl-C1-3 alkyl; and X isoptionally substituted phenyl, naphthyl, biphenyl, indanyl, benzofuranyl, benzothiophenyl, 1-tetralone-6-yl, C1-4 alkylenedioxy, pyridyl, furyl or thienyl. These compounds and pharmaceutical compositions containing them are useful as analgesic, antiinflammatory, diuretic, antitussive, anesthetic or neuroprotective agents, or an agent for treatment of stroke or functional bowel disease such as abdominal pain, for the treatment of a mammalian subject, especially a human subject.

  下式化合物 及其药学上可接受的盐，其中 R1 和 R2 独立地为氢、C1-4 烷基、C3-7 环烷基、C2-4 烯基、C1-4 烷氧基-C1-4 烷基、C1-4 硫代烷基-C1-4 烷基、苯基、苯基-C1-4 烷基、卤代 C1-4 烷基、C3-7 环烷基-C1-3 烷基或羟基-C1-4 烷基；或 R1 和 R2 与它们所连接的氮一起形成任选取代的、饱和或不饱和的 3-、4-、5-、6-或 7-成员杂环，其中含有一至两个杂原子，条件是该杂环不是吡咯烷基； R3 是氢、C1-4 烷基或羟基保护基团； Ar 是任选取代的苯基或苯基-C1-3 烷基；以及 X 是任选取代的苯基、萘基、联苯基、茚基、苯并呋喃基、苯并噻吩基、1-四氢萘-6-基、C1-4 烷二氧基、吡啶基、呋喃基或噻吩基。 这些化合物和含有它们的药物组合物可用作镇痛剂、抗炎剂、利尿剂、止咳剂、麻醉剂或神经保护剂，或治疗中风或功能性肠病（如腹痛）的药物，用于治疗哺乳动物，特别是人类。