2-([亚氨基](苯基)甲基]氨基)乙酸 | 32683-07-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-([亚氨基](苯基)甲基]氨基)乙酸
• 英文名称: N-carboxymethylbenzamidine
• 英文别名: N-<α-Imino-benzyl>-glycin；Benzamidino-essigsaeure；N²-Benzamidino-essigsaeure；N-(carboxymethyl)phenylamidine；(benzimidoylamino)acetic acid；2-[amino(phenyl)methylidene]azaniumylacetate
• CAS: 32683-07-1
• 化学式: C₉H₁₀N₂O₂
• mdl: MFCD01935985
• 分子量: 178.191
• InChiKey: ZDTNJTKQGYFSCI-UHFFFAOYSA-N

物化性质

• 熔点：
  210°
• 沸点：
  210°C
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-([亚氨基](苯基)甲基]氨基)乙酸 在 sodium ethanolate 作用下， 以 aq. phosphate buffer 、 乙醇 、 水 、 异丙醇 为溶剂， 反应 19.5h， 生成 5-氨基-6-氧代-2-苯基-1(6h)-嘧啶乙酸
  参考文献：
  名称：

  An Improved Synthesis of 5-Acylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic Acid from Glycine with Readily Removable Protecting Groups

  摘要：

  Concise synthesis of N-acyl-5-amino-6-oxo-2-phenyl-1(6H)-yrimidineacetic acid was achieved by cyclization reaction of 2-alkyl-4-lkoxymethylene-5(4H)-oxazolone with N-(carboxymethyl)benzamidine, while a similar reaction with sodium salt of 2-alkyl-4-hydroxymethylene-5(4H)-xazolones gave a mixture of regioisomers of the pyrimidinone. N-Acyl groups (acetyl or phenylacetyl) of the pyrimidinone derivatives were readily cleaved under very mild conditions with weak base or enzyme. Thus, the process enabled us to synthesize the drug candidate without exchanging N-protecting group. Since the starting oxazolones were easily prepared from N-acylglycine, the synthetic route can be used for the large scale synthesis of the key intermediate for several enzyme inhibitors.

  DOI：

  10.3987/com-12-12518
• 作为产物：
  描述：

  N²-Benzamidino-acetonitril 在 盐酸 作用下， 生成 2-([亚氨基](苯基)甲基]氨基)乙酸
  参考文献：
  名称：

  Julia,M.; Huynh Dinh Tam, Bulletin de la Societe Chimique de France, 1971, p. 1303 - 1308

  摘要：

  DOI：

文献信息

• Production method of pyrimidine derivative, intermediate therefor
  申请人：Ajinomoto Co., Inc.

  公开号：EP1529778A1

  公开（公告）日：2005-05-11

  The present invention relates to a production method of compound (XV), which includes hydrolysis of compound (I) to give compound (II), then reaction with reagent (III) to give compound (IV), then reaction with compound (V) to give compound (VI), then condensation with compound (XII) to give compound (XI), and preferably deprotection by an enzyme reaction. This method is an advantageous production method of a pyrimidine derivative and a synthetic intermediate useful as an enzyme inhibitor. wherein P is an alkyl group and the like, M is sodium and the like, R1 and R2 are each an alkyl group and the like, R3 is an alkyl group optionally having substituent(s) and the like, X is a halogen atom and the like, R5 is an alkyl group optionally having substituent(s) and the like, R6 is a hydrogen atom and the like, R7 is an aralkyl group optionally having substituent(s) and the like, and Y is a heteroaryl group optionally having substituents and the like.

  本发明涉及一种化合物（XV）的生产方法，包括将化合物（I）水解得到化合物（II），然后与试剂（III）反应得到化合物（IV），然后与化合物（V）反应得到化合物（VI），然后与化合物（XII）缩合得到化合物（XI），最好通过酶反应脱保护。该方法是一种有利的嘧啶衍生物和合成中间体的生产方法，可用作酶抑制剂。其中P是烷基等，M是钠等，R1和R2分别是烷基等，R3是可选地具有取代基的烷基等，X是卤素原子等，R5是可选地具有取代基的烷基等，R6是氢原子等，R7是可选地具有取代基的芳基烷基等，Y是可选地具有取代基的杂环芳基等。
• PROCESSES FOR PRODUCTION OF PYRIMIDINE DERIVATIVES AND INTERMEDIATES
  申请人：Ajinomoto Co., Inc.

  公开号：EP1695967A1

  公开（公告）日：2006-08-30

  Compound (I) is reacted with compound (II) to give compound (III), which is then reacted with compound (IX) to give compound (VIII), which is then preferably deprotected by an enzyme reaction to give compound (XII). The present invention provides an advantageous process for preparing a pyrimidine derivative useful as an enzyme inhibitor, and a synthetic intermediate: wherein P is an alkyl group and the like, R1 and R2 are alkyl groups and the like, R3 is an alkyl group optionally having substituent(s) and the like, R4 is a hydrogen atom and the like, R5 is an aralkyl group optionally having substituent(s) and the like, and Y is a heteroaryl group optionally having substituent(s) and the like.

  化合物（I）与化合物（II）发生反应得到化合物（III），然后与化合物（IX）发生反应得到化合物（VIII），然后最好通过酶反应去保护得到化合物（XII）。本发明提供了一种有利的制备嘧啶衍生物的方法，该衍生物可用作酶抑制剂，以及一种合成中间体：其中P为烷基基团等，R1和R2为烷基基团等，R3为可选地具有取代基的烷基基团等，R4为氢原子等，R5为可选地具有取代基的芳基烷基基团等，Y为可选地具有取代基的杂环芳基基团等。
• Process for the production of 2-substituted
  申请人：Lonza Ltd.

  公开号：US05696272A1

  公开（公告）日：1997-12-09

  A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## in which glycine is reacted with an imido ester of the general formula: ##STR2## and the resultant intermediate is converted into the product by a Vilsmeier reagent. The 2-substituted 5-chloroimidazole-4-carbaldehydes are valuable intermediates for the preparation of pharmaceuticals or herbicidally active compounds.

  一种制备2-取代的5-氯咪唑-4-甲醛的方法，其一般公式为：##STR1## 在该方法中，甘氨酸与一般公式为：##STR2## 的亚胺酯发生反应，产生的中间体通过威尔斯迈尔试剂转化为产物。这些2-取代的5-氯咪唑-4-甲醛是制备药物或除草活性化合物的有价值的中间体。
• Process for preparing pyrimidine compound
  申请人：Takahashi Daisuke

  公开号：US20050165234A1

  公开（公告）日：2005-07-28

  Azlactone Compound (2) is reacted with Amidine Compound (3) to give Pyrimidine Compound (1) which is useful as an intermediate for the production of enzyme inhibitors (e.g., elastase inhibitor, chymase inhibitor etc.): wherein each symbol is as defined in the specification.

  Azlactone化合物(2)与Amidine化合物(3)反应，得到嘧啶化合物(1)，该化合物可用作生产酶抑制剂（例如弹性蛋白酶抑制剂，胰蛋白酶抑制剂等）的中间体：其中每个符号如规范所定义。
• Process for the preparation of pyrimidine derivative, intermediate therefor and process for the preparation thereof
  申请人：Takahashi Daisuke

  公开号：US20050176966A1

  公开（公告）日：2005-08-11

  The present invention relates to a process for the preparation of compound (XV), which includes hydrolysis of compound (I) to give compound (II), then reaction with reagent (III) to give compound (IV), then reaction with compound (V) to give compound (VI), then condensation with compound (XII) to give compound (XI), and preferably deprotection by an enzyme reaction. This method is useful for the preparation of a pyrimidine derivative and a synthetic intermediate, which is useful as an enzyme inhibitor.

  本发明涉及一种制备化合物（XV）的方法，包括将化合物（I）水解得到化合物（II），然后与试剂（III）反应得到化合物（IV），然后与化合物（V）反应得到化合物（VI），然后与化合物（XII）缩合得到化合物（XI），并最好通过酶反应去保护基。该方法对于制备嘧啶衍生物和合成中间体非常有用，该中间体可用作酶抑制剂。