5-氰基戊酸铵盐 | 5238-61-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-氰基戊酸铵盐
• 英文名称: 5-cyanovaleric acid ammonium salt
• 英文别名: Azane;5-cyanopentanoic acid；azane;5-cyanopentanoic acid
• CAS: 5238-61-9
• 化学式: C₆H₈NO₂*H₄N
• 分子量: 144.173
• InChiKey: DYSXBURFMWFBSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氰基戊酸铵盐 以95%的产率得到5-氰基戊酸
  参考文献：
  名称：

  Preparation of lactams from aliphatic .alpha., .omega.-dinitriles

  摘要：

  已经开发了一种从脂肪族α，ω-二腈制备五元环或六元环内酰胺的方法。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性的催化剂或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的组合将脂肪族α，ω-二腈在水溶液中转化为ω-腈羧酸铵盐。然后，在水溶液中通过加氢将ω-腈羧酸铵盐直接转化为相应的内酰胺，而无需分离中间体ω-腈羧酸或ω-氨基羧酸。当脂肪族α，ω-二腈在α-碳原子上也非对称取代时，腈酶以大于98%的区域选择性产生由水解ω-腈基而得到的ω-腈羧酸铵盐，从而在随后的加氢过程中仅产生两种可能内酰胺产物中的一种。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。

  公开号：

  US05908954A1
• 作为产物：
  描述：

  己二腈 反应 86.0h， 以6.6%的产率得到己二酰二胺
  参考文献：
  名称：

  Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

  摘要：

  Five- and six-membered ring lactams have been prepared by first converting an aliphatic alpha,omega-dinitrile to an omega-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax: facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The omega-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate omega-cyanocarboxylic acid or omega-aminocarboxylic acid. Only one of two possible lactam products was produced from alpha-alkyl-substituted alpha,omega-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the omega-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.

  DOI：

  10.1021/jo9804386

文献信息

• Nitrilase-producing acidovorax facilis
  申请人：E. I. du Pont de Nemours & Company

  公开号：US06066490A1

  公开（公告）日：2000-05-23

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α，ω-二腈制备五元环或六元环内酰胺的方法已被开发。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂将脂肪族α，ω-二腈转化为水溶液中的ω-腈酸铵盐。然后，在水溶液中直接将ω-腈酸铵盐转化为相应的内酰胺，而不需要分离中间体ω-腈酸或ω-氨基酸。当脂肪族α，ω-二腈在α-碳原子处也非对称取代时，腈酶以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈酸铵盐，从而在随后的氢化反应中仅产生两种可能的内酰胺产物之一。还提供了一种热处理过程，用于选择理想的区域选择性腈酶或腈水合酶活性并破坏不良活性。
• Preparation of lactams from aliphatic .alpha.,.omega.-dinitriles
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05814508A1

  公开（公告）日：1998-09-29

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α，ω-二腈制备五元环或六元环内酰胺的方法已经开发出来。在该过程中，使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂，首先将脂肪族α，ω-二腈在水溶液中转化为ω-腈基羧酸铵盐。然后，直接在水溶液中将ω-腈基羧酸铵盐转化为相应的内酰胺，而不需要分离中间体ω-腈基羧酸或ω-氨基羧酸。当脂肪族α，ω-二腈在α-碳原子处也被非对称取代时，腈酶以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈基羧酸铵盐，从而在随后的氢化过程中仅产生两种可能的内酰胺产品之一。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。
• Preparation of lactams from aliphatic .alpha..omega.-dinitriles
  申请人：E. I. du Pont de Nemours and Company

  公开号：US06077955A1

  公开（公告）日：2000-06-20

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α,ω-双腈制备五元环或六元环内酰胺的方法已经开发出来。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂将脂肪族α,ω-双腈转化为在水溶液中的ω-腈酸铵盐。然后，将ω-腈酸铵盐直接在水溶液中氢化为相应的内酰胺，而无需分离中间体ω-腈酸或ω-氨基酸。当脂肪族α,ω-双腈在α-碳原子处也不对称取代时，腈酶会以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈酸铵盐，从而在随后的氢化过程中仅产生两种可能的内酰胺产品之一。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。
• Preparation of lactams from aliphatic .alpha.,.omega.-Dinitiles
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05922589A1

  公开（公告）日：1999-07-13

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha., .omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α，ω-二腈制备五元或六元环内酰胺的方法已经开发出来。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂，在水溶液中将脂肪族α，ω-二腈转化为ω-腈基羧酸铵盐。然后直接在水溶液中将ω-腈基羧酸铵盐转化为相应的内酰胺，而不需要分离中间体ω-腈基羧酸或ω-氨基羧酸。当脂肪族α，ω-二腈在α-碳原子处也不对称取代时，腈酶以大于98％的区域选择性水解ω-腈基团，从而产生ω-腈基羧酸铵盐，在随后的氢化过程中仅产生两种可能的内酰胺产品之一。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。
• Preparation of lactams from aliphatic - dinitriles
  申请人：E.I. DUPONT DE NEMOURS AND COMPANY

  公开号：EP1449830A1

  公开（公告）日：2004-08-25

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic α,ω-dinitriles has been developed. In the process an aliphatic α,ω-dinitrile is first converted to an ammonium salt of an ω-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the ω-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate ω-nitrilecarboxylic acid or ω-aminocarboxylic acid. When the aliphatic α,ω-dinitrile is also unsymmetrically substituted at the α-carbon atom, the nitrilase produces the ω-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the ω-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  我们开发了一种从脂肪族 α,ω-二腈制备五元环或六元环内酰胺的工艺。在该工艺中，首先在水溶液中使用具有脂肪族硝化酶（EC 3.5.5.7）活性或兼具腈水解酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂将脂肪族 α,ω-二腈转化为ω-腈羧酸的铵盐。然后，ω-腈羧酸的铵盐在水溶液中通过氢化作用直接转化为相应的内酰胺，而无需分离中间体ω-腈羧酸或ω-氨基羧酸。当脂肪族α,ω-二腈在α-碳原子上也被非对称取代时，硝化酶水解ω-腈基产生的ω-腈羧酸铵盐的区域选择性超过 98%，从而在随后的氢化过程中只产生两种可能内酰胺产物中的一种。此外，还提供了一种热处理工艺，用于选择理想的区域选择性腈酶或腈水解酶活性，同时破坏不理想的活性。