(+/-)-2-(2-methoxyphenyl)-piperidine | 118577-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+/-)-2-(2-methoxyphenyl)-piperidine
• 英文别名: 2-(24'-methoxyphenyl)piperidine；2-(2-methoxyphenyl)piperidine；2-(2'-Methoxyphenyl)-piperidin
• CAS: 118577-00-7
• 化学式: C₁₂H₁₇NO
• mdl: MFCD02663553
• 分子量: 191.273
• InChiKey: ZZBFEVGWWXDHPT-UHFFFAOYSA-N

物化性质

• 沸点：
  288.5±33.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(2-methoxyphenyl)-piperidine 在 氢氧化钾 、 cesium fluoride 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 8-Methoxy-2-methyl-2,3,4,5,6,7-hexahydro-1H-benzo[c]azonine
  参考文献：
  名称：

  Rearrangement of 1-methyl-2-(substituted-phenyl)piperidinium 1-methylides in a neutral medium

  摘要：

  DOI：

  10.1021/jo00265a022
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 sodium tetrahydroborate 、 碘 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (+/-)-2-(2-methoxyphenyl)-piperidine
  参考文献：
  名称：

  A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions

  摘要：

  Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.

  DOI：

  10.1021/ol035746r

文献信息

• Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles
  作者：Rachel S. Heath、Marta Pontini、Shahed Hussain、Nicholas J. Turner

  DOI：10.1002/cctc.201500822

  日期：2016.1

  novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining (R)‐6‐hydroxy‐d‐nicotine oxidase (6‐HDNO) with an (R)‐IRED, a panel of racemic 2‐substituted piperidines and pyrrolidines were deracemized to yield the (S)‐amines in high yields and enantiomeric excess values. Other N‐heterocycles were deracemized with monoamine oxidase (MAO‐N)

  开发了一种新型的胺氧化酶（AO）/亚胺还原酶（IRED）系统，用于消旋外消旋胺。通过将（R）-6-羟基d-烟碱氧化酶（6-HDNO）与（R）-IRED结合使用，将一组外消旋的2个取代的哌啶和吡咯烷脱脂，以高产率获得（S）-胺和对映体超值。其他N杂环用单胺氧化酶（MAO-N）或6-HDNO与氨硼烷结合进行脱氮，这使得可以将两种酶的脱氮方法与涉及化学还原剂的方法进行比较。
• Compounds active towards bromodomains
  申请人：NUEVOLUTION A/S

  公开号：US10752640B2

  公开（公告）日：2020-08-25

  Disclosed are compounds towards bromodomains, pharmaceutical compositions containing the compounds and use of the compounds in therapy.

  所公开的是针对溴化多聚酶的化合物、含有这些化合物的药物组合物以及这些化合物在治疗中的用途。
• Removal of the Pyridine Directing Group from α-Substituted<i>N</i>-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp³C–H Functionalization
  作者：Veerle Smout、Aldo Peschiulli、Stefan Verbeeck、Emily A. Mitchell、Wouter Herrebout、Patrick Bultinck、Christophe M. L. Vande Velde、Didier Berthelot、Lieven Meerpoel、Bert U. W. Maes

  DOI：10.1021/jo401521y

  日期：2013.10.4

  Two strategies, "hydrogenation-hydride reduction" and. "quaternization-hydride reduction", are reported, that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed Sp(3) C-H functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally. equally effective. Only in the case of 2,6-disubstituted piperidines, could the "quaternization-hydride reduction" strategy not be used. The "hydrogenation-hydride reduction" protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (+/-)-solenopsin A (trans diastereoisomer) and (+/-)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire: ant alkaloids could be determined via VCD spectroscopy.
• SHIRAI, NAOHIRO;SUMIYA, FUMIHIKO;SATO, YOSHIRO;HORI, MIKIKO, J. ORG. CHEM., 54,(1989) N, C. 836-840
  作者：SHIRAI, NAOHIRO、SUMIYA, FUMIHIKO、SATO, YOSHIRO、HORI, MIKIKO

  DOI：——

  日期：——
• COMPOUNDS ACTIVE TOWARDS BROMODOMAINS
  申请人：NUEVOLUTION A/S

  公开号：US20170349607A1

  公开（公告）日：2017-12-07

  Disclosed are compounds towards bromodomains, pharmaceutical compositions containing the compounds and use of the compounds in therapy.