3-甲基-5-戊基-2-呋喃十一烷酸 | 57818-37-8

• 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: 3-甲基-5-戊基-2-呋喃十一烷酸
• 英文名称: 11-<(3-methyl-5-pentyl)-2-furyl>undecanoic acid
• 英文别名: 11-[(3-methyl-5-pentylfuran)-2-yl]undecanoic acid；11-(3-methyl-5-pentylfuran-2-yl)undecanoic acid；3-Methyl-5-pentyl-2-furanundecanoic acid
• CAS: 57818-37-8
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: QDTBMEGPXZUECM-UHFFFAOYSA-N

物化性质

• 沸点：
  459.1±40.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲基-5-戊基-2-呋喃十一烷酸 、 重氮甲烷 生成 methyl 11-(3-methyl-5-pentyloxolan-2-yl)undecanoate
  参考文献：
  名称：

  SCHEINKONIG, JOSEF;SPITELLER, GERHARD, LIEBIGS ANN. CHEM.,(1991) N, C. 451-453

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-二溴-2-呋喃甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium dihydroxide copper(l) iodide 、 氢气 、 二乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 3-甲基-5-戊基-2-呋喃十一烷酸
  参考文献：
  名称：

  Sequential Pd(0)-catalyzed reactions for the construction of multiple substituted furans. A short synthesis of the F5 furan fatty acid1a

  摘要：

  4,5-Dibromofurfural (1) undergoes a regioselective Pd(0)-catalyzed C-C bond forming reaction at its C-5 position to yield the corresponding furans 3. The second bromine substituent in C-4 position can be substituted by a methyl group in a subsequent Pd(0)-catalyzed cross coupling reaction. The furan fatty acid 12 and its benzyl ester 13 were prepared in a short synthetic sequence using this method. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00054-9

文献信息

• Optimised total syntheses of the F-furan fatty acids F 5 and F 6 and some deuterated derivatives
  作者：David W. Knight、Andrew W.T. Smith

  DOI：10.1016/j.tet.2015.05.061

  日期：2015.9

  with methyl lithium, which gave trideuterated derivatives 16 of the F6 acid by using CD3Li. The two acids 2 and 3 proved very unstable; thus, if samples are to be stored for extended periods, this should be as an ester and not as the free acids. This instability does raise questions regarding previously determined levels of these free acids (and perhaps some of their structurally close relatives) in various

  完整描述了F 5-和F 6-呋喃脂肪酸2和3的优化合成。关键步骤包括使用由硝酸银（I）或碘引发的5-内消旋环化反应，由单个3-炔烃-1,2-二醇6形成呋喃。通过与丙烯酸苄酯的交叉复分解和氢化，实现了最终羧酸功能的引入和一碳同系物。中间体碘代呋喃的碘-甲基交换是通过直接用甲基锂处理而实现的，使用CD 3 Li可以得到三重氘的F 6酸衍生物16。两种酸2和3证明非常不稳定；因此，如果样品要长期保存，应以酯而不是游离酸的形式存在。这种不稳定性确实引起了人们对各种天然来源中这些游离酸（可能还有一些其结构上的近亲）的先前确定水平的质疑。
• Total synthesis of the naturally occurring furanoid fatty acid, F5
  作者：Charles M. Marson、Steven Harper

  DOI：10.1016/s0040-4039(97)10481-6

  日期：1998.1

  The furanoid fatty acid F5 has been synthesized using a mercury(II) catalyzed isomerization of 2-(1,2-oxiranylcyclododecyl)-3-nonyn-2-ol.

  使用2-（1,2-环氧乙烷基环十二烷基）-3-壬基-2-醇的汞（II）催化异构化合成呋喃酮脂肪酸F 5。
• The Preparation of 2,3,5-Tri- and 2,3-Disubstituted Furans by Regioselective Palladium(0)-Catalyzed Coupling Reactions: Application to the Syntheses of Rosefuran and the F5 Furan Fatty Acid
  作者：Thorsten Bach、Lars Krüger

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2045::aid-ejoc2045>3.0.co;2-6

  日期：1999.9

  regioselective Pd0-catalyzed coupling reaction at the C-2 carbon atom. With alkynes the corresponding 2-alkynylfurans 4 and 5 were accessible (49–97% yield). Alkyl-, aryl-, and alkenylzinc reagents gave the 2-substituted furans 8 starting from compound 2 (66–84% yield). The 2-allylfurans 8e and 8f were obtained by a regioselective Stille coupling in 79% and 73% yield. The latter reaction was also applied to

  5-受体取代的 2,3-二溴呋喃 1 和 2 在 C-2 碳原子上进行了区域选择性 Pd0 催化的偶联反应。对于炔烃，可以得到相应的 2-炔基呋喃 4 和 5（产率 49-97%）。烷基-、芳基-和烯基锌试剂从化合物 2 开始得到 2-取代的呋喃 8（产率 66-84%）。2-烯丙基呋喃 8e 和 8f 通过区域选择性 Stille 偶联获得，产率分别为 79% 和 73%。后一反应也适用于母体 2,3-二溴呋喃 (27) 并产生取代产物 28 (60% 产率)。随后的 Pd0 催化反应通过甲基脱溴在 3-位引入甲基，成功地进行了 2-炔基-3-溴呋喃与 MeZnCl 和 PdCl2(PPh3)2 作为催化剂在 THF（回流）中得到化合物 13-16和 24 (67–76%) 以及使用 SnMe4 和 PdCl2[P(o-Tol)3]2 作为催化剂在 DMA (90 °C) 中制备 2-烯丙基-3-溴呋喃
• Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes
  作者：Charles M. Marson、Steven Harper

  DOI：10.1021/jo980856a

  日期：1998.12.1

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.
• BIODEGRADABLE COMPOSITIONS AND MATERIALS
  申请人：Putnam David Aaron

  公开号：US20100104625A1

  公开（公告）日：2010-04-29

  The present invention provides compounds of Formula I, materials comprising one or more compounds of Formula I and one or more biologically active agents, pharmaceutical compositions comprising an inventive material and a pharmaceutically acceptable excipient, methods of making compounds of Formula I, methods of making inventive materials, and methods of using pharmaceutical compositions comprising an inventive material and a pharmaceutically acceptable excipient.