(2S)-2-benzylpiperidine | 99112-94-4

• 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: (2S)-2-benzylpiperidine
• 英文别名: (S)-2-benzylpiperidine
• CAS: 99112-94-4
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: ITXCORRITGNIHP-LBPRGKRZSA-N

物化性质

• 熔点：
  46.2°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-benzylpiperidine 、 1-萘甲酰氯 生成 [(2S)-2-benzylpiperidin-1-yl]-naphthalen-1-ylmethanone
  参考文献：
  名称：

  MEYERS, A. I.;DICKMAN, D. A.;BAILEY, TH. R., J. AMER. CHEM. SOC., 1985, 107, N 26, 7974-7978

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[(1R)-2-(甲氧基甲基氨基)-2-氧代-1-(苯基甲基)乙基]氨基甲酸1,1-二甲基乙基酯 在 Grubbs catalyst first generation 、 盐酸 、 lithium aluminium tetrahydride 、 水 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 生成 (2S)-2-benzylpiperidine
  参考文献：
  名称：

  Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding

  摘要：

  Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoylglycerol (2 -AG) that activates cannabinoid CB1 receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4 -substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5 -position of the piperidine ring provided ultrapotent inhibitor 38 (DH376) with picomolar activity. Compound 38 temporarily reduces fasting -induced refeeding of mice, thereby emulating the effect of cannabinoid' CB1-receptor inverse agonists. This was mirrored by 39 (DO34) but also by the negative control compound 40 (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple molecular targets.

  DOI：

  10.1021/acs.jmedchem.6b01482

文献信息

• [EN] 1,2,4 TRIAZOLO [4, 3 -A] [1,5] BENZODIAZEPIN-5 (6H) -ONES AS AGONISTS OF THE CHOLECYSTOKININ-1 RECEPTOR (CCK-IR)<br/>[FR] 1,2,4 TRIAZOLO[4,3-A][1,5] BENZODIAZÉPIN-5(6H)-ONES UTILISÉES COMME AGONISTES DU RÉCEPTEUR DE LA CHOLÉCYSTOKININE-1 (CCK-1R)
  申请人：PFIZER

  公开号：WO2010067233A1

  公开（公告）日：2010-06-17

  This invention relates to CCK-1 R agonists of Formula (I) wherein R1-R5 and X are as defined in the specificiation, as well as pharmaceutical compositions containing the compounds and methods of use of the compounds and compositions. The compounds are useful in treating obesity, type 2 diabetes and associated diseases.

  这项发明涉及到式（I）中的CCK-1 R激动剂，其中R1-R5和X如规范中所定义，以及含有这些化合物的药物组合物和这些化合物和组合物的使用方法。这些化合物在治疗肥胖症、2型糖尿病及相关疾病方面是有用的。
• Catalytic Asymmetric Synthesis of Substituted Morpholines and Piperazines
  作者：Huimin Zhai、Andrey Borzenko、Ying Yin Lau、Shin Hye Ahn、Laurel L. Schafer

  DOI：10.1002/anie.201206826

  日期：2012.12.3

  Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3‐substituted morpholines and the diastereoselective synthesis of 2,5‐substituted piperazines.

  在以下两种情况下：3族取代吗啉的模块化和对映选择性合成以及2，5-取代哌嗪的非对映选择性合成中具有第4类金属催化的加氢胺化作用。
• Catalytic Kinetic Resolution of Cyclic Secondary Amines
  作者：Michael Binanzer、Sheng-Ying Hsieh、Jeffrey W. Bode

  DOI：10.1021/ja209472h

  日期：2011.12.14

  The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.

  外消旋环胺的催化拆分是通过对映选择性酰胺化反应实现的，该反应具有非手性 N-杂环卡宾催化剂和新型手性异羟肟酸助催化剂协同作用。反应在室温下进行，不产生非挥发性副产物，并通过水萃取提供富含对映体的胺。
• Stereoelectronic Basis for the Kinetic Resolution of N-Heterocycles with Chiral Acylating Reagents
  作者：Sheng-Ying Hsieh、Benedikt Wanner、Philip Wheeler、André M. Beauchemin、Tomislav Rovis、Jeffrey W. Bode

  DOI：10.1002/chem.201402818

  日期：2014.6.10

  The kinetic resolution of N‐heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N‐heterocycles by using easily prepared reagents. A transition‐state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed

  N-杂环与手性酰化剂的动力学拆分揭示了胺酰化中以前未被认识的立体电子效应。与新的非手性异羟肟酸酯相结合，这种效应使得通过使用易于制备的试剂来拆分各种N-杂环成为可能。还提出了一种过渡态模型来合理化这种动力学解析的立体化学结果。
• Diastereopure Preparation of α-Benzotriazolyl 1-Azacycloalka[2,1-<i>b</i>][1,3]-oxazines and their Application as Versatile Chiral Precursors
  作者：Yuefei Hu、Xuenong Xu、Jun Lu、Rui Li、Zongming Ge、Yanmei Dong

  DOI：10.1055/s-2003-43353

  日期：——

  A group of diastereopure α-benzotriazolyl 1-azacyclo­alka[2,1-b][1,3]oxazines were prepared from non-racemic Betti base and they were employed as the versatile precursors for the preparation of chiral ligands and chiral substituted azacyclics with significant advantages in the stereoselectivity.

  制备了一组非外消旋的贝蒂碱衍生的立体纯α-苯并三氮唑基1-氮杂环烷[2,1-b][1,3]恶嗪。这些化合物被用作制备手性配体和手性取代氮杂环化合物的前体，具有显著的立体选择性优势。