6-[(氨基羰基)氨基]己酸 | 1468-42-4

• 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: 6-[(氨基羰基)氨基]己酸
• 英文名称: 6-ureidohexanoic acid
• 英文别名: ε-ureidocaproic acid；ε-Ureido-capronsaeure；6-(carbamoylamino)hexanoic acid
• CAS: 1468-42-4
• 化学式: C₇H₁₄N₂O₃
• mdl: MFCD06655749
• 分子量: 174.2
• InChiKey: BQNWWHFSEXYHKU-UHFFFAOYSA-N

物化性质

• 熔点：
  174-178 °C(Solv: water (7732-18-5))
• 沸点：
  354.6±34.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090
• 储存条件：
  存储温度应保持在2-8°C，并需避免光照。

反应信息

• 作为反应物：
  描述：

  6-[(氨基羰基)氨基]己酸 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 120.0h， 生成 Benzyl 3-[6-[[1-(butylamino)-1-oxopropan-2-yl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Focused Library of Tetrahydropyrimidinone Amides via a Tandem Biginelli-Ugi Multi-Component Process

  摘要：

  我们制备了一个由 30 个四氢嘧啶酮酰胺组成的第二代聚焦文库。其设计基于 Hsp70 调节剂的结构。这个小型文库展示了串联多组分反应在生物先导分子结构-活性关系研究中的实用性。串联 Biginelli-Ugi 多组分反应促进了四个不同取代基的有效变化，只需两个一锅反应就能合成库中的成员。

  DOI：

  10.1055/s-2006-949648
• 作为产物：
  描述：

  1,3-二(5-羧基戊基)硫脲 在 氨 、 水 、 双氧水 、 硝酸 、 sodium nitrite 作用下， 生成 6-[(氨基羰基)氨基]己酸
  参考文献：
  名称：

  Amino Acids. V. 1,3-Di-(ι-carboxyalkyl)-thioureas and Their Chemistry

  摘要：

  DOI：

  10.1021/ja01539a058

文献信息

• Protecting Group Free Synthesis of Carboxyl-substituted Dihydropyrimidines Through Biginelli Reaction
  作者：Eugeniy N. Ostapchuk、Andrey S. Plaskon、Oleksandr O. Grygorenko、Andrey A. Tolmachev、Sergey V. Ryabukhin

  DOI：10.1002/jhet.1568

  日期：2013.11

  acetoacetic acid derivatives, and various carboxyl‐containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono‐substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one‐pot, protecting group free synthesis of dihydropyrimidines

  探索了氯三甲基硅烷促进的苯甲醛，乙酰乙酸衍生物和各种含羧基尿素的Biginelli型反应。发现脲取代基的空间负荷强烈影响反应结果。特别是，该方法仅在带有脂肪族或芳香族基团的直链单取代尿素中有效。该方法可以进行具有保护功能的二氢嘧啶的单锅，无保护基的合成。
• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20040009995A1

  公开（公告）日：2004-01-15

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I 1 or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3 , R 4 and R 7 are defined in the specification, Z is SO or SO 2 , and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用公式I的化合物的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中在规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本文中定义的芳香族或杂环芳基。
• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Combating fungi with 1-(.omega.-substituted
  申请人：Bayer Aktiengesellschaft

  公开号：US04188401A1

  公开（公告）日：1980-02-12

  1-(.omega.-Substituted pentyl)-3-(2-cyano-acetyl)-ureas of the formula ##STR1## in which R represents R.sup.1, CO--R.sup.2, CO--NH--R.sup.3 or CO--OR.sup.4, R.sup.1 represents unsubstituted alkyl with 1 to 10 carbon atoms; or represents substituted alkyl with 1 to 4 carbon atoms, which contains, as a substituent, a vinyl group, an alkynyl group with up to 4 carbon atoms, an alkylcarbonyl group with 2 to 5 carbon atoms, an alkoxycarbonyl group with 2 to 5 carbon atoms, an alkenoxycarbonyl or alkynoxycarbonyl group with 4 to 5 carbon atoms, an aminocarbonyl group, an N-alkylaminocarbonyl or N-cycloalkylaminocarbonyl group with up to 7 carbon atoms in either case or a N-phenylaminocarbonyl group, which can optionally have C.sub.1 -C.sub.4 alkyl and/or chlorine as further substituents on the phenyl radical; or represents benzyl, which can be substituted in the aromatic part by a methyl, methoxy, methylenedioxy, nitro, trifluoromethyl, benzoyl, monochlorobenzoyl, dichlorobenzoyl, phenyl or phenoxy group or by 1 to 4 chlorine atoms; R.sup.2 represents a straight-chain or branched, saturated or unsaturated hydrocarbon radical with up to 8 carbon atoms, which can be substituted by chlorine or bromine or by a cyano group, R.sup.3 represents a straight-chain or branched alkyl radial with up to 11 carbon atoms, which can be substituted by a cyano group of by an alkoxycarbonyl radical with up to 5 carbon atoms, or represents a phenyl radical, which can be substituted y a methyl, nitro or trifluoromethyl group or by chlorine, R.sup.4 represents a saturated or unsaturated aliphatic group with up to 4 carbon atoms, Q represents CN, CO--NH.sub.2, COOH or CO--OR.sup.5, and R.sup.5 denotes an alkyl group with 1 to 4 carbon atoms, which possess fungicidal properties.

  公式为##STR1##的1-(.omega.-取代戊基)-3-(2-氰乙酰基)-脲类化合物，其中R代表R.sup.1，CO--R.sup.2，CO--NH--R.sup.3或CO--OR.sup.4，R.sup.1代表具有1至10个碳原子的未取代烷基；或代表具有1至4个碳原子的取代烷基，其中包含乙烯基、具有最多4个碳原子的炔基、具有2至5个碳原子的烷基羰基、具有2至5个碳原子的烷氧羰基、具有4至5个碳原子的烯氧羰基或炔氧羰基、氨基羰基、N-烷基氨基羰基或N-环烷基氨基羰基，每种情况中最多含有7个碳原子，或N-苯胺氨基羰基，苯基团上的苯基团可以选择性地具有C.sub.1 -C.sub.4烷基和/或氯作为苯基团上的进一步取代基；或代表苄基，可以通过甲基、甲氧基、亚甲二氧基、硝基、三氟甲基、苯甲酰基、对氯苯甲酰基、邻二氯苯甲酰基、苯基或苯氧基团或1至4个氯原子在芳香部分取代，R.sup.2代表具有最多8个碳原子的直链或支链、饱和或不饱和的烃基，可以通过氯或溴或氰基取代，R.sup.3代表具有最多11个碳原子的直链或支链烷基，可以通过氰基或最多5个碳原子的烷氧羰基基取代，或代表苯基，可以通过甲基、硝基或三氟甲基基或氯取代，R.sup.4代表具有最多4个碳原子的饱和或不饱和脂肪族基，Q代表CN，CO--NH.sub.2，COOH或CO--OR.sup.5，R.sup.5表示具有1至4个碳原子的烷基，具有杀真菌性能。