2-Hydroxy-4-methoxybenzaldehyde, pentyl ether | 938270-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Hydroxy-4-methoxybenzaldehyde, pentyl ether
• 英文别名: 4-methoxy-2-pentoxybenzaldehyde
• CAS: 938270-81-6
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: HHKQGMUKYNDPMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-4-methoxybenzaldehyde, pentyl ether 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 生成 4-methoxy-2-pentyloxy-benzoic acid
  参考文献：
  名称：

  Discovery and Structural Modification of 1-Phenyl-3-(1-phenylethyl)urea Derivatives as Inhibitors of Complement

  摘要：

  A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7I, and 7o) greatly improving their activity. Optimized compound 7I has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7I inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.

  DOI：

  10.1021/ml300005w

文献信息

• [DE] VERFAHREN ZUR HERSTELLUNG VON EINEM 1-(3-CYCLOPENTYLOXY-4-ALKOXYPHENYL)-4-OXOCYCLOHEXANCARBONITRIL<br/>[EN] METHOD FOR PRODUCING A 1-(3-CYCLOPENTENYLOXY- 4-ALKOXYPHENYL)-4- OXOCYCLOHEXANECARBONITRILE<br/>[FR] PROCEDE POUR PRODUIRE UN 1-(3-CYCLOPENTYLOXY- 4-ALCOXYPHENYL)-4- OXOCYCLOHEXANECARBONITRILE
  申请人：LONZA AG

  公开号：WO1999011607A1

  公开（公告）日：1999-03-11

  (DE) Beschrieben wird ein neues Verfahren zur Herstellung von 1-(3-Cyclopentyloxy-4-alkoxyphenyl)-4-oxocyclohexancarbonitril der allgemeinen Formel (I). Dabei wird ein 4-Cyan-4-(3-cyclopentyloxy-4-methoxyphenyl)-heptandisäuredialkylester der allgemeinen Formel (II), in Gegenwart einer Base zu einem 5-Cyan-5-(3-cyclopentyloxy-4-alkoxyphenyl)-2-oxocyclohexancarbonsäurealkylester der allgemeinen Formel (III) cyclisiert, dann die Verbindung der allgemeinen Formel (III) mit einem Alkalimetallhydrogencarbonat neutralisiert und letztere wird dann in Gegenwart von einem Alkalimetallcarbonat zum Endprodukt, gemäss Formel (I), decarboxyliert.(EN) Disclosed is a novel method for producing 1-(3-cyclopentenyloxy- 4- alkoxyphenyl)-4- oxocyclohexanecarbonitrile of general formula (I). A 4-cyano-4- (3-cyclopentenyloxy- 4-methoxyphenyl)- heptanediaciddialkyl ester of general formula (II) is cyclized in the presence of a base to form a 5-cyano-5- (3-cyclopentyloxy-4- alkoxyphenyl)-2- oxocyclohexane carbonic acid ester of general formula (III), then the compound of general formula (III) is neutralized with an alkali metal hydrogen carbonate and finally decarboxylated in the presence of an alkali metal carbonate to form an end product according to formula (I).(FR) L'invention concerne un nouveau procédé de production de 1-(3-cyclopentyloxy- 4-alcoxyphényl)- 4-oxocyclohéxanecarbonitrile de formule générale (I). A cet effet, un dialkylester de diacide de 4-cyano-4- (3-cyclopentyloxy- 4-méthoxyphényl)- heptane de formule générale (II) est cyclisé en présence d'une base pour former un alkylester d'acide carboxylique de 5-cyano-5- (3-cyclopentyloxy-4- alcoxyphényl)-2- oxocyclohéxane de formule générale (III), puis le composé de formule générale (III) est neutralisé avec un carbonate d'hydrogène de métal alcalin avant d'être décarboxylé en présence d'un carbonate de métal alcalin pour former le produit final correspondant à la formule (I).

  描述了一种制备1-(3-环戊氧基-4-烷氧基苯基)-4-氧环己烷腈（通式(I)）的新方法。具体而言，将4-氰基-4-(3-环戊氧基-4-甲氧基苯基)戊二酸二甲酯（通式(II)），在碱性条件下环化为5-氰基-5-(3-环戊氧基-4-烷氧基苯基)-2-氧环己烷羧酸甲酯（通式(III)），然后用碱金属碳酸氢盐对通式(III)的化合物进行中和，再在碱金属碳酸盐的存在下脱羧，最终得到通式(I)的产物。 Invention concerns a new process for producing 1-(3-cyclopentyloxy-4-alkoxyphenyl)-4-oxocyclohexanecarbonitrile of general formula (I). For this purpose, a dialkyl ester of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)heptanedioic acid of general formula (II) is cyclized in the presence of a base to form an alkyl ester of 5-cyano-5-(3-cyclopentyloxy-4-alkoxyphenyl)-2-oxocyclohexanecarboxylic acid of general formula (III). The compound of general formula (III) is then neutralized with an alkali metal hydrogen carbonate and finally decarboxylated in the presence of an alkali metal carbonate to form the final product according to formula (I). 本发明涉及1-(3-环戊氧基-4-烷氧基苯基)-4-氧环己烷腈（通式(I)）的一种新型制备方法。为此，将4-氰基-4-(3-环戊氧基-4-甲氧基苯基)庚二酸二甲酯（通式(II)）在碱性条件下环化，得到5-氰基-5-(3-环戊氧基-4-烷氧基苯基)-2-氧环己烷羧酸甲酯（通式(III)）。然后，将通式(III)的化合物用碱金属碳酸氢盐进行中和，最后在碱金属碳酸盐的存在下脱羧，得到通式(I)的最终产物。
• VERFAHREN ZUR HERSTELLUNG VON EINEM 1-(3-CYCLOPENTYLOXY-4-ALKOXYPHENYL)-4-OXOCYCLOHEXANCARBONITRIL
  申请人：LONZA AG

  公开号：EP1009735A1

  公开（公告）日：2000-06-21
• Discovery and Structural Modification of 1-Phenyl-3-(1-phenylethyl)urea Derivatives as Inhibitors of Complement
  作者：Mei Zhang、Xiao-Ying Yang、Wei Tang、Tom W. L. Groeneveld、Pei-Lan He、Feng-Hua Zhu、Jia Li、Wei Lu、Anna M. Blom、Jian-Ping Zuo、Fa-Jun Nan

  DOI：10.1021/ml300005w

  日期：2012.4.12

  A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7I, and 7o) greatly improving their activity. Optimized compound 7I has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7I inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.