(S,E)-2-(7-methoxytetradec-4-enyloxy)-tetrahydro-2H-pyran | 142088-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (S,E)-2-(7-methoxytetradec-4-enyloxy)-tetrahydro-2H-pyran
• 英文别名: 2-((S,E)-7-methoxytetradec-4-enyloxy)tetrahydro-2Hpyran；(E,7S)-7-methoxy-1-tetrahydropyran-2-yloxy-4-tetradecene；2-[(E,7S)-7-methoxytetradec-4-enoxy]oxane
• CAS: 142088-54-8
• 化学式: C₂₀H₃₈O₃
• 分子量: 326.52
• InChiKey: FNPZQIJVXCCZJY-CPBJYODASA-N

物化性质

• 沸点：
  418.1±45.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-2-(7-methoxytetradec-4-enyloxy)-tetrahydro-2H-pyran 在 chromium(VI) oxide 、 N-羟基-7-氮杂苯并三氮唑 、 硫酸 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.5h， 生成 (E,7S)-N-[(2S)-1-[[(2S,3S,4R)-3-hydroxy-5-[(2S)-3-methoxy-5-oxo-2-propan-2-yl-2H-pyrrol-1-yl]-4-methyl-5-oxopentan-2-yl]amino]-1-oxopropan-2-yl]-7-methoxy-N-methyltetradec-4-enamide
  参考文献：
  名称：

  Total synthesis of malyngamide X and its 7′S-epi isomer

  摘要：

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.035
• 作为产物：
  描述：

  4-四氢吡喃基氧基-丁烷-1-醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (S,E)-2-(7-methoxytetradec-4-enyloxy)-tetrahydro-2H-pyran
  参考文献：
  名称：

  Novel malyngamide structural analogs: synthesis and biological evaluation

  摘要：

  In the course of our search for new anticancer agents, a series of novel malyngamide derivatives were synthesized by sharpless asymmetric epoxidation, followed by Julia-Kocinski olefination reactions as key reaction sequence. Anticancer activities of all these derivatives were screened against IMR-32, SF-295, SKNSH, HeLa, Colon-502713, SW-620, and Hop-62 cell lines for the first time.

  DOI：

  10.1007/s00044-013-0466-y

文献信息

• Synthesis of (4E)-7-methoxytetradec-4-enoic acid: a novel fatty acid from lyngbya majuscula
  作者：Craig B. Fryhle、Paul G. Williard、Rybak Carol M.

  DOI：10.1016/s0040-4039(00)74202-x

  日期：1992.4

  The synthesis of (4E)-7-methoxytetradec-4-enoic acid is described. This novel fatty acid is found in the blue-green algae . and is incorporated as the amide in several nitrogeneous metabolites, including the fish antifeedant compound malyngamide A.

  描述了（4E）-7-甲氧基十四烷基-4-烯酸的合成。在蓝绿色藻类中发现了这种新的脂肪酸。并作为酰胺掺入几种含氮代谢产物中，包括鱼类拒食化合物麦芽酰胺A。
• Total synthesis of malyngamide M and isomalyngamide M
  作者：Jie Chen、Zi-Fa Shi、Ling Zhou、An-Le Xie、Xiao-Ping Cao

  DOI：10.1016/j.tet.2010.03.004

  日期：2010.5

  The stereoselective synthesis of malyngamide M (1) was accomplished in nine steps from o-cresol in 12% overall yield. The key steps involved the Wittig reaction of an α-NHBoc aryl ketone 4 for the introduction of vinyl chloride functionality, an amidation of lyngbic acid 3 with a secondary amine 2 for the framework of target molecule, and an isomerization of a (Z)-vinyl chloride to the (E)-configuration

  麦芽酰胺M（1）的立体选择性合成是从邻甲酚开始的9个步骤，总产率为12％。关键步骤包括用于引入氯乙烯官能团的α- NHBoc芳基酮4的Wittig反应，针对目标分子框架的lyngbic acid 3与仲胺2的酰胺化以及（Z）-的异构化使用二苯甲酮作为光敏剂将氯乙烯制成（E）-构型。还合成了异麦芽酰胺M（Z - 1）。
• Novel malyngamide structural analogs: synthesis and biological evaluation
  作者：G. Venkateswar Reddy、T. Vijaya Kumar、B. Siva、K. Suresh Babu、P. V. Srinivas、Irum Sehar、A. K. Saxena、J. Madhusudana Rao

  DOI：10.1007/s00044-013-0466-y

  日期：2013.10

  In the course of our search for new anticancer agents, a series of novel malyngamide derivatives were synthesized by sharpless asymmetric epoxidation, followed by Julia-Kocinski olefination reactions as key reaction sequence. Anticancer activities of all these derivatives were screened against IMR-32, SF-295, SKNSH, HeLa, Colon-502713, SW-620, and Hop-62 cell lines for the first time.
• Total synthesis of malyngamide X and its 7′S-epi isomer
  作者：Suchada Suntornchashwej、Khanit Suwanborirux、Minoru Isobe

  DOI：10.1016/j.tet.2007.01.035

  日期：2007.4

  Stereoselective syntheses of malyngamide X (1) and its 7'(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7' in the molecules of natural and synthetic 1, and 7'(S)-epi 1 was confirmed by NMR chiral solvation experiments. (c) 2007 Elsevier Ltd. All rights reserved.