(R)-N-苄基哌啶-3-甲酰胺 | 168466-80-6

• 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)-N-苄基哌啶-3-甲酰胺
• 英文名称: (R)-N-benzylpiperidine-3-carboxamide
• 英文别名: (R)-1-(benzyl)nipecotamide；(R)-1-benzylnipecotamide；(3R)-1-benzylpiperidine-3-carboxamide
• CAS: 168466-80-6
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: QKDBCVUPRORMPD-GFCCVEGCSA-N

物化性质

• 沸点：
  390.4±31.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-苄基哌啶-3-甲酰胺 在 sodium hypochlorite 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以55%的产率得到(R)-3-氨基-1-苄基哌啶
  参考文献：
  名称：

  METHOD FOR PRODUCING OPTICALLY ACTIVE 3-AMINOPIPERIDINE OR SALT THEREOF

  摘要：

  本发明涉及一种生产光学活性3-氨基哌啶或其盐的方法。在该方法中，通过在有机体衍生的酶源存在下，立体选择性水解一个混合的尼皮科酰胺来获得光学活性尼皮科酰胺和光学活性尼皮科酸，然后通过酰化、霍夫曼重排、氨基保护基的去除和进一步的去保护，将光学活性尼皮科酰胺转化为光学活性氨基哌啶或其盐；或者通过用BOC进行选择性保护、霍夫曼重排和进一步的去保护，将光学活性尼皮科酰胺转化为光学活性氨基哌啶或其盐。通过本发明，可以从廉价且易得的起始材料中通过简单的工业制造方法生产出一种作为药物中间体有用的光学活性3-氨基哌啶或其盐。

  公开号：

  US20100105917A1
• 作为产物：
  描述：

  (R,S)-N-苄基哌啶-3-甲酰胺 在 sodium hydroxide 作用下， 反应 60.0h， 以99.8%的产率得到
  参考文献：
  名称：

  METHOD FOR PRODUCING OPTICALLY ACTIVE 3-AMINOPIPERIDINE OR SALT THEREOF

  摘要：

  本发明涉及一种生产光学活性3-氨基哌啶或其盐的方法。在该方法中，通过在有机体衍生的酶源存在下，立体选择性水解一个混合的尼皮科酰胺来获得光学活性尼皮科酰胺和光学活性尼皮科酸，然后通过酰化、霍夫曼重排、氨基保护基的去除和进一步的去保护，将光学活性尼皮科酰胺转化为光学活性氨基哌啶或其盐；或者通过用BOC进行选择性保护、霍夫曼重排和进一步的去保护，将光学活性尼皮科酰胺转化为光学活性氨基哌啶或其盐。通过本发明，可以从廉价且易得的起始材料中通过简单的工业制造方法生产出一种作为药物中间体有用的光学活性3-氨基哌啶或其盐。

  公开号：

  US20100105917A1

文献信息

• AMIDE OR THIOAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PAIN
  申请人：CHANG Chia-Ping

  公开号：US20100105777A1

  公开（公告）日：2010-04-29

  The present invention relates to novel compounds, pharmaceutical compositions comprising the same, use of said compounds for the manufacture of a medicament for treatment of pain and disorders related thereto as well as a method for treatment of pain and disorders related thereto, wherein said compounds are administered. The compounds are represented by the general formula (I), as further defined in the specification.

  本发明涉及新型化合物、包含该化合物的药物组合物，以及使用该化合物制造治疗疼痛和相关疾病的药物以及治疗疼痛和相关疾病的方法，其中该化合物被给予。该化合物由一般式(I)表示，具体定义详见说明书。
• Method for producing optically active 3-aminopiperidine or salt thereof
  申请人：Kaneka Corporation

  公开号：US08338142B2

  公开（公告）日：2012-12-25

  The present invention relates to a method for producing an optically active 3-aminopiperidine or salt thereof. In the method, a racemic nipecotamide is stereoselectively hydrolyzed to obtain an optically active nipecotamide and an optically active nipecotic acid in the presence of an enzyme source derived from an organism, and then the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by aroylation, Hofmann rearrangement, deprotection of the amino group and further deprotection; or the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by selective protection with BOC, Hofmann rearrangement and further deprotection. It is possible by the present invention to produce an optically active 3-aminopiperidine or salt thereof useful as a pharmaceutical intermediate from an inexpensive and easily available starting material by easy method applicable to industrial manufacturing.

  本发明涉及一种制备光学活性3-氨基哌啶或其盐的方法。在该方法中，利用来源于生物体的酶源，在立体选择性水解中得到光学活性的尼佩考胺和光学活性的尼佩考酸，然后通过酰化、霍夫曼重排、氨基保护基的去除和进一步去保护，或者通过选择性BOC保护、霍夫曼重排和进一步去保护将光学活性的尼佩考胺转化为光学活性的氨基哌啶或其盐。本发明可以通过简单的工业制造方法，从廉价易得的起始材料中制备出用于制药中间体的光学活性3-氨基哌啶或其盐。
• NOVEL AMIDASE, GENE FOR THE SAME, VECTOR, TRANSFORMANT, AND METHOD FOR PRODUCTION OF OPTICALLY ACTIVE CARBOXYLIC ACID AMIDE AND OPTICALLY ACTIVE CARBOXYLIC ACID BY USING ANY ONE OF THOSE ITEMS
  申请人：Kaneka Corporation

  公开号：EP2128258A1

  公开（公告）日：2009-12-02

  The present invention has its object to provide a novel polypeptide having amidase activity to selectively hydrolyze S-enantiomer in racemic nipecotamide, a DNA encoding the polypeptide, a vector containing the DNA, a transformant transformed with the vector, and a method for producing an optically active carboxylic acid amide and an optically active carboxylic acid in which a racemic carboxylic acid amide is hydrolyzed with the polypeptide or the transformant.

  本发明的目的是提供一种新型多肽，它具有酰胺酶活性，可选择性地水解外消旋尼泊金酰胺中的S-对映体；提供一种编码该多肽的DNA；提供一种含有该DNA的载体；提供一种用该载体转化的转化体；以及提供一种生产光学活性羧酸酰胺和光学活性羧酸的方法，其中外消旋羧酸酰胺是用该多肽或转化体水解的。
• Characterization of an enantioselective amidase from Cupriavidus sp. KNK-J915 (FERM BP-10739) useful for enzymatic resolution of racemic 3-piperidinecarboxamide
  作者：Masutoshi Nojiri、Naoaki Taoka、Yoshihiko Yasohara

  DOI：10.1016/j.molcatb.2014.08.016

  日期：2014.11

  A novel amidase (CsAM) acting on (R,S)-N-benzyl-3-piperidinecarboxamide was purified from Cupriavidus sp. KNK-J915 (FERM BP-10739) and characterized. The enzyme acts on (R,S)-N-benzyl-3-piperidinecarboxamide S-selectively to yield (R)-N-benzyl-3-piperidinecarboxamide. Analytical gel filtration column chromatography and SDS-PAGE revealed that the enzyme is a tetramer with a subunit of approximately 47 kDa. It has a broad substrate spectrum against nitrogen-containing heterocyclic amides. Its optimal pH and temperature are 8.0-9.0 and 50 degrees C, respectively. The CsAM gene was cloned and sequenced, and it was found to comprise 1341 bp and encode a polypeptide of 46,388 Da. The deduced amino acid sequence exhibited 78% identity to that of a putative amidase (CnAM) from Cupriavidus necator JMP134. The cultured cells of recombinant Escherichia coli producing CnAM could be used for the S-selective hydrolysis of (R,S)-N-benzyl-3-piperidinecarboxamide but could not be used for the S-selective hydrolysis of (R,S)-3-piperidinecarboxamide because of its very low level of selectivity. In contrast, the cultured cells of recombinant E. coli producing CsAM could hydrolyze both (R,S)-N-benzyl-3-piperidinecarboxamide and (R,S)-3-piperidinecarboxamide with high S-selectivity. (C) 2014 Elsevier B.V. All rights reserved.
• Amide or thioamide derivatives and their use in the treatment of pain
  申请人：Chang Chia-Ping

  公开号：US20070197653A1

  公开（公告）日：2007-08-23

  The present invention relates to novel compounds, pharmaceutical compositions comprising the same, use of said compounds for the manufacture of a medicament for treatment of pain and disorders related thereto as well as a method for treatment of pain and disorders related thereto, wherein said compounds are administered. The compounds are represented by the general formula (I), as further defined in the specification.