7-C-Phenyl-D-gluco-hept-2-enono-γ-lactone | 142955-65-5

• 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: 7-C-Phenyl-D-gluco-hept-2-enono-γ-lactone
• 英文别名: (S)-5-((1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one；(2S)-2-[(1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl]-2H-furan-5-one
• CAS: 142955-65-5
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: FJBARMGOBUNTIH-WKSBVSIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-C-Phenyl-D-gluco-hept-2-enono-γ-lactone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到(+)-goniofufurone
  参考文献：
  名称：

  （+）-gonfufufurone，（+）-7- epi- goniofufurone，（+）-crassalactones B和C的简明合成

  摘要：

  从已知的d-葡萄糖酸-δ-内酯衍生物9到6到7步实现了（+）-goniofufurone，（+）-7- epi- goniofufurone，（+）-crassalactones B和C的简洁有效合成。用酸介导的级联环化反应一锅构建呋喃呋喃酮双环骨架。

  DOI：

  10.1016/j.tetlet.2019.06.001
• 作为产物：
  描述：

  (1S)-1-phenylprop-2-en-1-ol 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 四氧化锇 、 甲基磺酰胺 、 AD-mix β 、 氢气 、 palladium(II) hydroxide 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 93.0h， 生成 7-C-Phenyl-D-gluco-hept-2-enono-γ-lactone
  参考文献：
  名称：

  （+）- exo-和（-）- exo- brevicomins，（+）-内切-和（-）-内切-brevicomins，（+）-和（-）-心脏丁醇化物，（+）-goniofufurone的立体选择性总合成

  摘要：

  聚集信息素（+）- exo -brevicomin（9a），（-）- exo -brevicomin（9b），（+）-内-brevicomin（9c），（-）- endo -brevicomin（9d）和苯乙烯内酯（+）-心脏丁醇内酯（14a），（-）-心脏丁醇内酯（14b）和（+）-goniofufurone（19a）是从对映体纯的高度官能化的呋喃类化合物糖基砌块（1a - d中获得的））涉及类似的合成策略，因此使这些呋喃类化合物糖类在面向多样性的合成（DOS）中成为非常有用的构建基块。

  DOI：

  10.1016/j.tet.2011.04.014

文献信息

• Total synthesis of antitumour agent (+)-goniofufurone
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1039/c39920000810

  日期：——

  The absolute configuration of the natural goniofufurone is confirmed as 1 by a short and stereoselective synthesis in eight steps from D-glycero-D-gulo-heptono-γ-lactone with an overall yield of 12.7%.

  通过D-甘油-D-古洛-庚酮-γ-内酯的短程立体选择性合成，分八步合成，天然的角尼呋喃酮的绝对构型为1，总产率为12.7%。
• Gonibutenolides A and B: serendipitous syntheses, relative and absolute configuration
  作者：Tony K. M. Shing、Vincent W.-F. Tai、Hon-Chung Tsui

  DOI：10.1039/c39940001293

  日期：——

  The relative and absolute stereochemistries of natural goniobutenolides A and B are established as 1 and 2 respectively by short syntheses of them and their 8-epimers.

  通过简短合成天然高尼丁内酯 A 和 B 及其 8-表聚物，确定它们的相对和绝对立体化学结构分别为 1 和 2。
• Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-<i>epi</i>-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo0702342

  日期：2008.1.1

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.
• Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1021/jo00115a030

  日期：1995.5

  Practical and efficient syntheses of a number of styryl lactones with various structural complexities were accomplished from commercially available and inexpensive D-glycero -D-gulo-heptono-gamma-lactone (D-glucoheptonic gamma-lactone)(11). Lactone 11 was converted by four sequential reactions (acetonation, selective deacetonation, glycol cleavage oxidation, and Grignard reaction) into key intermediates 3,5-O-isopropylidene-1, 1,6-tri-C-phenyl-D-glycero-D-gulo-hexitol (15) and 3,5-O-isopropylidene-1,1,6-tri-C-phenyl-L-glycero-D-gulo- hexitol(16). The alcohol 15 was transformed via a glycol cleavage oxidation and a Z-selective Wittig reaction into enoate Z-9 which underwent hydrolysis and an intramolecular Michael-type cyclization to give (+)-goniofufurone (1). Likewise, reaction of 16 afforded 7-epi-goniofufurone (2). Acylation and subsequent deacylation of 7-C-phenyl-D-gluco-hept-2-enono-gamma-lactone (20) readily gave (+)-goniobutenolide A (3) and (-)-goniobutenolide B (4), whereas treatment of (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate (Z-22) with DBU followed by acid hydrolysis and intramolecular Michael reaction provided (+)-goniopypyrone (5). Mesylation of 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enono-delta- lactone (27) followed by acid hydrolysis furnished (+)-altholactone (6). (+)-Goniotriol (7) and (+)-7-acetylgoniotriol (8) were readily obtained from the enoate Z-9. This work also provides a viable synthetic route for the construction of the enantiomers of the above styryl lactones for biological evaluation from the same starting material 11. Suggestions about the possible biosynthetic pathway of the styryl lactones are given.