dihydrodehydroacetic acid | 18781-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dihydrodehydroacetic acid
• 英文别名: 3-Acetyl-4-hydroxy-6-methyl-5,6-dihydro-pyran-2-one；5-acetyl-4-hydroxy-2-methyl-2,3-dihydropyran-6-one
• CAS: 18781-80-1
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: UXDFXEYZSDAXPT-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  363.5±42.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihydrodehydroacetic acid 生成
  参考文献：
  名称：

  Nedjar-Kolli, Bellara; Hamdi, Maamar; Perie, Jacques, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 543 - 547

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二氢-4-羟基-6-甲基-2H-吡喃-2-酮 在 sodium 作用下， 以 苯 为溶剂， 反应 6.5h， 生成 dihydrodehydroacetic acid
  参考文献：
  名称：

  Nedjar-Kolli, Bellara; Hamdi, Maamar; Perie, Jacques, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 543 - 547

  摘要：

  DOI：

文献信息

• Substituted 1, 4-thiazepine and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20020010169A1

  公开（公告）日：2002-01-24

  The present invention is directed to substituted 1,4-thiazepine and analogs thereof, represented by the general Formula I: 1 wherein the dashed lines, A 1 , A 2 , A 3 , X 1 and R 1 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of capases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被一般式I表示的取代的1,4-噻吩和其类似物，其中虚线、A1、A2、A3、X1和R1在此处被定义。本发明还涉及发现具有式I的化合物是卡泊酶激活剂和凋亡诱导剂。因此，本发明的卡泊酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，其中异常细胞的不受控制的生长和扩散。
• Evaluation of heteroatom-rich derivatives as antitubercular agents with InhA inhibition properties
  作者：Bachar Rébat Moulkrere、Beatrice S. Orena、Giorgia Mori、Nathalie Saffon-Merceron、Frédéric Rodriguez、Christian Lherbet、Nadji Belkheiri、Mohamed Amari、Pascal Hoffmann、Mokhtar Fodili

  DOI：10.1007/s00044-017-2064-x

  日期：2018.1

  Two series of heterocyclic compounds derived from 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (DHA) and 2-acetylbutyrolactone have been synthesized and characterized. The compounds were evaluated for their activities against Mycobacterium tuberculosis strain, and as inhibitors of InhA, a key enzyme involved in the type II fatty acid biosynthesis pathway of M. tuberculosis. Among the tested compounds

  两个系列的杂环化合物由3-乙酰基-4-羟基-6-甲基-2衍生ħ -吡喃-2-酮（DHA）和2-乙酰基丁内酯已被合成和表征。化合物及其对活动进行了评价的结核分枝杆菌菌株，并且如INHA，参与II型脂肪酸的生物合成途径中的关键酶的抑制剂的结核分枝杆菌。在测试的化合物中，一种DHA衍生物化合物2对分枝杆菌和InhA均显示出有希望的活性。还进行了对接研究，并给出了一些与当前结构知识兼容的新结构-活性趋势。
• Ayer, William A.; Villar, J. Daniel Figueroa, Canadian Journal of Chemistry, 1985, vol. 63, p. 1161 - 1165
  作者：Ayer, William A.、Villar, J. Daniel Figueroa

  DOI：——

  日期：——
• A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin
  作者：Igor P. Lokot、Felix S. Pashkovsky、Fedor A. Lakhvich

  DOI：10.1016/s0040-4020(99)00150-7

  日期：1999.4

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Total Synthesis and Stereochemistry of Alternaric Acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1021/jo00096a016

  日期：1994.8

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.