环戊烷-1,3-二羧酸 | 42856-47-3

• 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: 环戊烷-1,3-二羧酸
• 英文名称: N¹,N⁵-dibenzylglutaramide
• 英文别名: N,N'-dibenzylglutaramide；N,N'-dibenzyl-glutaramide；N,N'-Dibenzyl-glutaramid；N,N'-Dibenzyl-glutar amide；N,N'-dibenzylpentanediamide
• CAS: 42856-47-3
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: HOXOPIHPIRQXCD-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  戊二酸 、 苄胺 在 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 水 为溶剂， 以91%的产率得到环戊烷-1,3-二羧酸
  参考文献：
  名称：

  Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM

  摘要：

  Selective formation of carboxamides in an alcohol or water by an exceptionally convenient one-step procedure in which a condensing agent is simply added to a mixture of acids and amines has been achieved successfully by using a new condensing agent, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Activation of carboxylic acids by DMT-MM in the presence of amines and subsequent aminolysis of the resulting acyloxytriazine in alcoholic solvents occurred selectively and led to the formation of carboxamides in excellent yields. The rate of aminolysis of the acyloxytriazine intermediate can be estimated to be about 2x10(4) times greater than that of methanolysis. The amide/ester selectivity observed using DMT-MM was much larger than that obtained with DCC or EDC. Condensation of polar substrates, such as amino acid esters and their hydrochlorides, glucosamine hydrochloride, sodium acetate and dicarboxylic acids, proceeded successfully in MeOH, water or aqueous MeOH in good yields. The present reaction is technically quite simple and easy to achieve. It proceeds by simple mixing of acids, amines and DMT-MM without any additives, and the MeOH is readily removable by a rotary evaporator after completion of the reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01137-6

文献信息

• Hydrogen Bond Organocatalysis of Benzotriazole in Transamidation of Carboxamides with Amines
  作者：Thanh Binh Nguyen、Ali Al-Mourabit、Ludmila Ermolenko、Marie-Elise Tran Huu Dau

  DOI：10.3987/com-13-s(s)41

  日期：——

  systems (ring-opening of four-membered rings; (ii) intramolecular assistance, or both factors); (iii) use of moisture-sensitive and/or activation reagents (up to 2–3 equivalents; borate esters, dialkylformamide dialkyl acetals, AlCl3, AlMe3, HCl). Examples of transamidation from the Stahl's group provided an elegant possibility of preparing amides under mild † This paper is dedicated to Prof. Victor

  开发了一种苯并三唑催化胺与甲酰胺转酰胺化的新方法。简介 酰胺键在生命系统中无处不在，在生物有机化学和药物化学中发挥着关键作用。甲酰胺基被发现出现在超过 25% 的已知药物中。因此，酰胺形成是有机合成中最基本的反应之一。形成酰胺键的最常见策略是在化学计量的活化试剂存在下胺和羧酸之间的反应。对于这种方法，第一步是酸（酰基氯、酰基咪唑、酰基叠氮化物、酸酐和活性酯）的活化，然后是氨解。已经做出了很多努力来开发催化直接酰胺化。或者，羧酰胺和胺之间的转酰胺基反应是合成有机化学中一种有吸引力的工具。然而，在一般剧烈的加热条件下需要非催化的氨基转移。已经开发了利用活化试剂或催化剂的不同方法，目的是降低反应温度。尽管范围很广，但这些协议至少需要以下条件之一：（i）能量有利的系统（四元环的开环；（ii）分子内辅助，或两者兼而有之）；(iii) 使用湿度敏感和/或活化试剂（最多 2-3 当量；硼酸酯、二烷基甲酰
• Cleavage of 1,3-dicarbonyls through oxidative amidation
  作者：Phillip Biallas、Andreas P. Häring、Stefan F. Kirsch

  DOI：10.1039/c7ob00731k

  日期：——

  A mild and convenient protocol for the oxidative cleavage of 1,3-diketone compounds is described. Under metal-free conditions, the method converts the 1,3-dicarbonyls into amides when treated with (nBu4N)N3 and iodine in the presence of an amine at room temperature. Using this method, a range of 1,3-dicarbonyls with various structural motifs including sterically demanding substituents and ordinary

  描述了一种温和方便的方案，用于1,3-二酮化合物的氧化裂解。在无金属的条件下，该方法在室温下在胺的存在下用（n Bu 4 N）N 3和碘处理时，可将1,3-二羰基化合物转化为酰胺。使用这种方法，很容易将一系列具有各种结构基序的1,3-二羰基（包括空间上必不可少的取代基和普通官能团）片段化，并证明环状的1,3-二羰基可以通过开环直接转化为无环二酰胺。 。最初的机理研究表明，烯醇形式的叠氮化后是胺的亲核取代。
• N-BENZYLAMIDES AS DERIVATIVES FOR IDENTIFYING THE ACYL GROUP IN ESTERS^1,2
  作者：O. C. DERMER、JACK KING

  DOI：10.1021/jo01190a008

  日期：1943.3
• Onda; Kunugi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 690
  作者：Onda、Kunugi

  DOI：——

  日期：——