3-hexadecyl-4-methylfuran-2,5-dione | 71595-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-hexadecyl-4-methylfuran-2,5-dione
• 英文别名: 4-Hexadecyl-3-methyl-2,5-furandion；3-hexadecyl-4-methylmaleic anhydride；hexadecyl-methyl-maleic acid-anhydride；Hexadecyl-methyl-maleinsaeure-anhydrid
• CAS: 71595-37-4
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: NTFSJJZJIBCUOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hexadecyl-4-methylfuran-2,5-dione 在 磷化氢 、 氢碘酸 作用下， 生成 2-hexadecyl-3-methyl-succinic acid
  参考文献：
  名称：

  Kameda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 261,264; dtsch. Ref. S. 117, 120

  摘要：

  DOI：
• 作为产物：
  描述：

  Agaricinsaeure 生成 3-hexadecyl-4-methylfuran-2,5-dione
  参考文献：
  名称：

  Thoms; Vogelsang, Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 161

  摘要：

  DOI：

文献信息

• Expedient Synthesis, on Large Scale, of Aliphatic Chaetomellic Anhydrides from <i>N</i>-Allyl-2,2-dichlorocarboxyamides
  作者：Franco Ghelfi、Mariella Pattarozzi、Fabrizio Roncaglia、Valerio Giangiordano、Andrew F. Parsons

  DOI：10.1080/00397910903029974

  日期：2010.3.12

  Chaetomellic anhydride A and an analog (with two additional carbons) were obtained, on a preparative scale, starting from amides derived from the acylation of 2-(2-propenylamino)pyridine with 2,2-dichloropalmitic or 2,2-dichlorostearic acid. An alternative approach, in which the methyl substituent of the target anhydride is introduced by the carboxylic acid reactant and the long aliphatic chain is

  从衍生自 2-(2-丙烯基氨基)吡啶与 2,2-二氯棕榈酸或 2,2-二氯硬脂酸酰化的酰胺开始，以制备规模获得毛甲酸酐 A 和类似物（具有两个额外的碳）。另一种方法被证明是不可行的，其中目标酸酐的甲基取代基由羧酸反应物引入，并通过烯丙基氨基部分添加长脂肪链。
• Novel route to chaetomellic acid A and analogues: Serendipitous discovery of a more competent FTase inhibitor
  作者：Franco Bellesia、Seoung-ryoung Choi、Fulvia Felluga、Giuliano Fiscaletti、Franco Ghelfi、Maria Cristina Menziani、Andrew F. Parsons、C. Dale Poulter、Fabrizio Roncaglia、Massimo Sabbatini、Domenico Spinelli

  DOI：10.1016/j.bmc.2012.10.034

  日期：2013.1

  A new practical route to chaetomellic acid A (ACA), based on the copper catalysed radical cyclization (RC) of (Z)-3-(2,2-dichloropropanoyl)-2-pentadecylidene-1,3-thiazinane, is described. Remarkably, the process entailed: (i) a one-pot preparation of the intermediate N-alpha-perchloroacyl-2-(Z)-alkyliden-1,3-thia-zinanes starting from N-(3-hydroxypropyl)palmitamide, (ii) a two step smooth transformation of the RC products into ACA and (iii) only one intermediate chromatographic purification step. The method offers a versatile approach to the preparation of ACA analogues, through the synthesis of an intermediate maleic anhydride with a vinylic group at the end of the aliphatic tail, a function that can be transformed through a thiol-ene coupling. Serendipitously, the disodium salt of 2-(9-(butylthio)nonyl)-3-methylmaleic acid, that we prepared as a representative sulfurated ACA analogue, was a more competent FTase inhibitor than ACA. This behaviour was analysed by a molecular docking study. (C) 2012 Elsevier Ltd. All rights reserved.
• Asano; Ohta, Chemische Berichte, 1934, vol. 67, p. 1843
  作者：Asano、Ohta

  DOI：——

  日期：——
• US4725373A
  申请人：——

  公开号：US4725373A

  公开（公告）日：1988-02-16