5-(4-氯苯基)咪唑烷-2,4-二酮 | 6212-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-(4-氯苯基)咪唑烷-2,4-二酮
• 英文名称: 5-(p-chlorophenyl)hydantoin
• 英文别名: 5-(4-Chlorophenyl)imidazolidine-2,4-dione
• CAS: 6212-32-4
• 化学式: C₉H₇ClN₂O₂
• mdl: MFCD03970797
• 分子量: 210.62
• InChiKey: VPZYKVWVBSWFFL-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C
• 密度：
  1.404±0.06 g/cm3(Predicted)
• 溶解度：
  >31.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)咪唑烷-2,4-二酮 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 乙醚 为溶剂， 反应 48.5h， 生成 [2-[[1-(4-Chlorophenyl)-2-pyrrolidin-1-ylethyl]-methylamino]-1-(3,4-dichlorophenyl)-2-oxoethyl] acetate
  参考文献：
  名称：

  Synthesis and κ binding affinity of 1-(pyrrolidin-1-ylmethyl)-2-(N-methyl)-4-[(3,4-dichloro)phenyl]-1,2,3,4 tetrahydroisoquinolin-3(2H)-ones

  摘要：

  Diastereomeric forms of 1-(pyrrolidin-1-ylmethyl)-2-(N-methyl)-4-[(3,4-dichloro)phenyl]-1,2,3,4-tetrahydroisoquinoline-3(2h)-ones 3a and its chloro analog 3c were synthesized. Compounds 3a,c are related to the kappa-selective opiate ICI 199441 1 by linking the benzylic CH2 to the ortho position of the phenyl in 1. Compared with morphine, these compounds had lost in kappa and mu affinities; only cis-3a showed a modest kappa affinity. 1-Pyrrolidin-1-ylmethyl-N-[2-(3,4-dichlorphenyl)acetyl]-1,2,3,4-tetrahydroisoquinoline 2, which is also a cyclic congener of 1, was reported to display high kappa and mu affinity, and so a conformational study was undertaken on 1, 2 and 3a. This showed that, while active 2 extensively superposed on 1, 3a assumes another geometry which does not allow a fit with the pharmacophoric moieties of 1 and 2.

  DOI：

  10.1016/0223-5234(96)88263-8
• 作为产物：
  描述：

  4-氯苯甲醛 在 ammonium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 5-(4-氯苯基)咪唑烷-2,4-二酮
  参考文献：
  名称：

  Benzimidazoles having antithrombotic activity

  摘要：

  本发明涉及一般式中Ra到Rc、A、Ar和B所定义的新苯并咪唑，其互变异构体，立体异构体，混合物，前药，含有在生理条件下带负电荷的基团而不是羧基的衍生物及其盐，特别是与无机或有机酸或碱的生理可接受的盐，具有有价值的特性。上述一般式I中Rc表示氰基的化合物是制备一般式I中其他化合物的有价值的中间体，而上述一般式I中Rc表示权威要求1中提到的氨基甲酰基之一的化合物具有有价值的药理学特性，特别是抗血栓活性。

  公开号：

  US06248770B1

文献信息

• 一种连续快速制备DL-苯甘氨酸及其类似物的方法
  申请人：天宝动物营养科技股份有限公司

  公开号：CN109824531B

  公开（公告）日：2022-08-23

  本发明提供一种连续快速制备DL‑苯甘氨酸及其类似的方法，包括：将2‑羟基‑苯乙腈及其类似物（简称氰醇）与碳铵水溶液加入微通道反应器进行反应，控制反应温度为80～130℃，压力为0.5～2.0MPa，反应物在微通道内停留时间为1～8min，得到5‑苯基‑乙内酰脲及其类似物（简称海因）水溶液；将海因与碱加入微通道反应器进行反应，控制反应温度为120～200℃，压力为1.0～3.5MPa，反应物在微通道内的停留时间为1～8min，得到苯甘氨酸及其类似物盐水溶液，经酸化中和、结晶，得到苯甘氨酸及其类似物。本发明采用微通道反应器，大大缩短了反应时间，加快反应速率，减少了氰醇热解聚合，无副产物产生，产品收率高，清洁环保，降低了生产成本。
• Process for the production of D-alpha-amino acids
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0677585A1

  公开（公告）日：1995-10-18

  A process is described for the production of D-α-amino acids by the stereospecific conversion of racemic mixtures of 5-substituted hydantoins, where said conversion is carried out in the presence of a microorganism transformed with a plasmid capable of expressing at high levels and without inducers an enzymatic system capable of converting said hydandoins in the corresponding D-α-amino acids. A plasmid is also described comprising the genes which encode said enzymatic system and a microorganism selected from Escherichia coli or Bacillus subtilis transformed with said plasmid. D-α-amino acids are intermediates useful in the preparation of pharmacologically active substances, pesticides and sweeteners.

  描述了一种通过 5-取代的海因外消旋混合物的立体特异性转化生产 D-α-氨基酸的工艺，其中所述转化是在用质粒转化的微生物存在下进行的，该质粒能够高水平表达一种酶系统，该酶系统无需诱导剂即可将所述海因转化为相应的 D-α-氨基酸。 还描述了一种质粒，其中包括编码所述酶系统的基因和用所述质粒转化的大肠杆菌或枯草杆菌中的微生物。 D-α- 氨基酸是用于制备药理活性物质、杀虫剂和甜味剂的中间体。
• Stable mutants of D-N-alpha-carbamylase
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0677584A1

  公开（公告）日：1995-10-18

  The present invention relates to mutants of D-N-α-carbamylase wherein at least one of the cysteines in position 243, 250 and 279 of the amino acid sequence of the wild type enzyme is substituted with a different residue selected from natural amino acids; a recombinant plasmid comprising a nucleotidic sequence which encodes for at least one of the mutants of D-N-α-carbamylase, host microorganisms transformed with said plasmid and a process for the preparation of these mutants by the culture of said microorganisms. The mutants of D-N-α-carbamylase have a higher enzymatic stability than that of the wild type enzyme and are particularly useful in the preparation of D-α-amino acids providing an improvement in the production yields.

  本发明涉及D-N-α-氨基甲酰酶的突变体，其中野生型酶的氨基酸序列的243、250和279位的半胱氨酸中至少有一个被选自天然氨基酸的不同残基取代；重组质粒，其包含编码至少一种D-N-α-氨基甲酰酶突变体的核苷酸序列；用所述质粒转化的宿主微生物；以及通过培养所述微生物制备这些突变体的工艺。 与野生型酶相比，D-N-α-氨基甲酰酶的突变体具有更高的酶稳定性，尤其适用于制备 D-α-氨基酸，可提高产量。
• Thermostable mutants of D-N-alpha-Carbamoylase
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0780473A2

  公开（公告）日：1997-06-25

  The present invention relates to thermostable mutants of D-N-α-carbamoylase and means and methods for their preparation. Said thermostable mutants have an unaltered or improved activity with respect to the wild type enzyme and are particularly useful in the preparation of D-α-aminoacids.

  本发明涉及 D-N-α-氨基甲酰酶的恒温突变体及其制备方法。 与野生型酶相比，所述恒温突变体的活性没有改变或有所提高，特别适用于制备 D-α-氨基酸。
• Preparation of D-alpha-amino acids, using bacteria transformed with the carbamoylase-hydantoinase operon
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0775748A2

  公开（公告）日：1997-05-28

  In an improved process for the preparation of D-α-amino acids by the stereoselective conversion of racemic mixtures of 5-substituted hydantoins with an enzymatic system produced by a microorganism, the improvement consists in the fact that a microorganism is used transformed with the plasmid pSM700 cultivated at a temperature of between 20°C and 28°C. The use of this microorganism allows an improvement in the expression of the enzymatic system and an increase in the conversion rate of the racemic hydantoin to D-α-amino acid.

  一种通过微生物产生的酶系统立体选择性转化 5-取代的海因外消旋混合物来制备 D-α-氨基酸的改进工艺，其改进在于使用了一种在 20°C 至 28°C 温度下培养的转化了质粒 pSM700 的微生物。 使用这种微生物可以改善酶系统的表达，提高外消旋海因向 D-α-氨基酸的转化率。