2,3,4-tris(ethoxycarbonyl)cyclopentanone | 6261-04-7

• 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
• 英文名称: 2,3,4-tris(ethoxycarbonyl)cyclopentanone
• 英文别名: 4-oxo-cyclopentane-1,2,3-tricarboxylic acid triethyl ester；4-Oxo-cyclopentan-1,2,3-tricarbonsaeure-triaethylester；2,3,4-Triethoxycarbonyl-cyclopentanon
• CAS: 6261-04-7
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: NABWPCKBTAFKRH-UHFFFAOYSA-N

物化性质

• 沸点：
  171 °C(Press: 2 Torr)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tris(ethoxycarbonyl)cyclopentanone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 rac-4-oxocyclopentane-1,2-dicarboxylic acid
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of β-Amino Acid BAY 10-8888/PLD-118, a Novel Antifungal for the Treatment of Yeast Infections

  摘要：

  δ-氨基酸 BAY 10-8888/PLD-118 作为一种治疗酵母菌感染的新型抗真菌药物，目前正在进行 II 期临床研究。本文介绍了该化合物的高效不对称合成。关键步骤采用了高度对映选择性的奎宁介导的介酸酐中间体醇解。

  DOI：

  10.1055/s-2003-36265
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2,3,4-tris(ethoxycarbonyl)cyclopentanone
  参考文献：
  名称：

  Ranganathan, Current Science, 1940, vol. 9, p. 276

  摘要：

  DOI：

文献信息

• Further Study of Syntheses of<i>dl</i>-2,3-Dicarboxycyclopentylacetic Acids
  作者：Kazu Kurosawa、Heitaro Obara

  DOI：10.1246/bcsj.39.525

  日期：1966.3

  The assignment of the configuration of racemic trans-trans and cis-cis-2,3-dicarboxycyclopentylacetic acid previously proposed has been confirmed by the syntheses of these compounds through other unambiguous reaction sequences. The trans-cis-isomer has been prepared by the epimerization of the 3-carboxyl group of the cis-cis-isomer, but the attempt to synthesize the fourth isomer (cis-trans) has been

  先前提出的外消旋反式和顺式-顺式-2,3-二羧基环戊基乙酸的构型的分配已通过这些化合物的合成通过其他明确的反应序列得到证实。反式-顺-异构体已经通过顺-顺-异构体的3-羧基差向异构化制备，但合成第四个异构体（顺-反）的尝试没有成功。
• A Synthetic Route to (±)-Tetrahydroanhydroaucubigenone
  作者：Hiroshi Kimura、Heitaro Obara、Sei Takahashi

  DOI：10.1246/bcsj.55.3661

  日期：1982.11

  (±)-Tetrahydroanhydroaucubigenone was synthesized by partial reduction, followed by acid hydrolysis, of (4aRS,7RS,7aSR)-7-(methoxycarbonyl) octahydrocyclopenta[c]pyran-1,5-dione ethylene acetal, which was prepared from 2,3,4-tris(ethoxycarbonyl)cyclopentanone through 7 steps.

  (4aRS,7RS,7aSR)-7-（甲氧基羰基）八氢环戊并[c]吡喃-1,5-二酮乙烯缩醛是由 2,3,4-三（乙氧基羰基）环戊酮通过 7 个步骤部分还原并经酸性水解合成的。
• Syntheses of<i>dl</i>-Tetrahydroanhydrodesoxyaucubigenin and Related Compounds
  作者：Kazu Kurosawa、Heitaro Obara、Hisashi Uda

  DOI：10.1246/bcsj.39.530

  日期：1966.3

  The racemic tetrahydroanhydrodesoxyaucubigenin, one of the derivatives from a glycoside, aucubin, has been synthesized using cis-cis-2-(2′-hydroxyethyl)-5-methoxycarbonylcyclopentane-carboxylic acid δ-lactone as an intermediate. 6,7-Dimethoxycarbonyl-2-oxa-bicyclo[3.3.0]-octane has also been synthesized, and the mechanism of the base-catalyzed rearrangement of the naturally-derived tetrahydroanhydroaucubigenin

  外消旋四氢脱水脱氧桃花心苷是一种糖苷桃红素的衍生物，已使用顺式-顺式-2-(2'-羟乙基)-5-甲氧基羰基环戊烷-羧酸δ-内酯作为中间体合成。还合成了 6,7-二甲氧基羰基-2-氧杂-双环[3.3.0]-辛烷，并阐明了天然衍生的四氢无水橙花碱对甲苯磺酸盐的碱催化重排机制。
• Novel antifungal β-amino acids: synthesis and activity against Candida albicans
  作者：Joachim Mittendorf、Franz Kunisch、Michael Matzke、Hans-Christian Militzer、Axel Schmidt、Wolfgang Schönfeld

  DOI：10.1016/s0960-894x(02)00958-7

  日期：2003.2

  A series of novel beta-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. beta-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections. (C) 2002 Elsevier Science Ltd. All rights reserved.