cis,cis-muconic acid mononitrile | 73824-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: cis,cis-muconic acid mononitrile
• 英文别名: (2Z,4Z)-5-cyanopenta-2,4-dienoic acid
• CAS: 73824-86-9
• 化学式: C₆H₅NO₂
• 分子量: 123.111
• InChiKey: IZRBYWRHSHSUCQ-CCAGOZQPSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  306.5±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis,cis-muconic acid mononitrile 生成 6-氨基己酸
  参考文献：
  名称：

  DEMMIN T. R.; ROGIC M. M., J. ORG. CHEM., 1980, 45, NO 13, 2737-2739

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二酚 以40%的产率得到cis,cis-muconic acid mononitrile
  参考文献：
  名称：

  Preparation of muconic acid mononitriles and copper(II)-ammonia reagent

  摘要：

  取代和未取代的苯酚、邻二酚和邻苯二酚可通过与铜(II)-氨试剂反应转化为黏着酸单硝基脲。铜(II)-氨试剂可通过在液氨、氨水或吡啶中将氯化亚铜与氧或空气反应后加入氨或氨水来制备。黏着酸单硝基脲可用作单体或共聚单体，以及用于制造取代和未取代的6-氨基己酸、己内酰胺和聚酰胺的中间体。

  公开号：

  US04277419A1

文献信息

• Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ2701
  作者：Otto Meth-Cohn、Mei-Xiang Wang

  DOI：10.1039/a703904b

  日期：——

  or γ-sulfur is present. Hydrolysis of N,N-bis(2-cyanoethyl)anilines 4h–j takes place slowly affording exclusively the monoacids 5h–j while the monocyano amides 5o–p are obtained as the sole isolable product from rapid hydrolysis of the corresponding N,N-bis(2-cyanomethyl)butylamine 4o and N,N-bis(3-cyanopropyl)butylamine 4p. Higher homologues of arylimino- and butylimino-dinitriles are inert to enzymatic

  使用Rhodococcus sp在非常温和的条件下选择性地水解了多种二腈。AJ270。脂族二腈NC [CH 2 ] n CN 1进行区域选择性水解，得到的单官能酸2在腈官能团之间最多具有4个亚甲基，而n  > 4的单酸2获得的二酸3的收率很好。当将氧置于氰基的β，γ或δ或β-或γ-上时，带有醚键或硫化物键的二腈NC [CH 2 ] n X [CH 2 ] n CN 4被有效地转化为一元酸5。存在硫。N，N的水解双（2-氰乙基）苯胺的4H-j取而monocyano酰胺0-50 p如从相应的快速水解的唯一可分离产物获得缓慢发生，得到专门的一元酸5H-J Ñ，Ñ双（2-氰基）丁胺4o和N，N-双（3-氰基丙基）丁胺4p。芳基-和丁基亚氨基-二腈的较高同系物对酶促水解是惰性的。多种其它脂族二腈的已被容易地转化成单酸以良好至优异的产率，除了ö -phenylenediacetonitrile其给出ø
• Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270
  作者：Otto Meth-Cohn、Mei-Xiang Wang

  DOI：10.1039/a700859g

  日期：——

  Aliphatic dinitriles undergo regioselective hydrolysis with the title organism to give monoacids with up to four methylenes between the nitrile functions (optimally 2–3) or when either an oxygen is placed β, γ or δ to the nitrile (δ-placement being optimal) or β or γ (optimally γ) but not δ sulfur substituents are present; nitrogen substituents appear to behave as for oxygen but suffer a steric limitation of the size of the nitrogen substituent.

  脂肪族二腈在该有机体的催化下发生区域选择性水解，生成单酸，腈基之间最多可有四个亚甲基（最优为2-3个），或者当氧原子位于腈的β、γ或δ位时（以δ位最佳），或者在β或γ位时（最优为γ），但如果存在δ位的硫取代基则不行；氮取代基的行为类似于氧，但受到氮取代基尺寸的空间限制。
• Enzymatic hydrolysis of nitrites and dinitriles
  作者：Petra Hönicke-Schmidt、Manfred P. Schneider

  DOI：10.1039/c39900000648

  日期：——

  An immobilized enzyme system derived from Rhodococcus sp. catalyses under neutral conditions the hydrolysis of nitriles (1)–(6) and dinitriles (7) and (8) into the corresponding acids (1a)–(6a) and monocyano carboxylic acids (7a) and (8a), respectively.

  固定的酶系统来源于红球菌。在中性条件下催化腈（1）–（6）和二腈（7）和（8）水解为相应的酸（1a）–（6a）和单氰基羧酸（7a）和（8a）。
• Preparation of muconic acid mononitriles and copper(II)-ammonia reagent therefor
  申请人：ALLIED CORPORATION

  公开号：EP0009369A1

  公开（公告）日：1980-04-02

  Substituted and unsubstituted phenols, catechols and orthobenzoquinones are converted to muconic acid mononitriles by reaction with copper(II)-ammonia reagent. The copper(II)-ammonia reagents can be prepared by the reaction of cuprous chloride with oxygen or air in liquid ammonia or in ammonium hydroxide or in pyridine followed by addition of ammonia or ammonium hydroxide. The muconic acid mononitriles are useful as monomers or comonomers and as intermediates in the manufacture of substituted and unsubstituted 6-aminocaproic acids, caprolactams and polyamides.

  取代和未取代的苯酚、儿茶酚和邻苯醌可通过与铜（II）-氨试剂反应转化为单腈基粘多酸。铜（II）-氨试剂可通过氯化亚铜与氧气或空气在液氨或氢氧化铵或吡啶中反应，然后加入氨或氢氧化铵制备。粘酸单腈类可用作单体或共聚单体，以及制造取代和未取代的 6-氨基己酸、己内酰胺和聚酰胺的中间体。
• Cis, cis muconic acid mononitrile and copper (II) salts thereof
  申请人：ALLIED CORPORATION

  公开号：EP0045527A2

  公开（公告）日：1982-02-10

  Phenol, catechol and orthobenzoquinone are converted to cis,cis-muconic acid mononitrile and its copper(II) salts by reaction with copper(ll)-ammonia reagent. The copper(II)-ammonia reagents can be prepared by the reaction of cuprous chloride with oxygen or air in liquid ammonia or in ammonium hydroxide or in pyridine followed by addition of ammonia or ammonium hydroxide. The muconic acid mononitrile is useful as a monomer or comonomer and as an intermediate in the manufacture of substituted and unsubstituted 6-aminocaproic acids, caprolactams and polyamides.

  苯酚、邻苯二酚和邻苯醌可通过与铜(ll)-氨试剂反应转化为顺式、顺式-粘多酸一腈及其铜(II)盐。铜（II）-氨试剂可通过氯化亚铜与氧气或空气在液氨或氢氧化铵或吡啶中反应，然后加入氨或氢氧化铵来制备。粘酸单腈可用作单体或共聚单体，也可用作制造取代和未取代的 6-氨基己酸、己内酰胺和聚酰胺的中间体。