4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone | 151830-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone
• 英文别名: (4R,4aR,8aS)-4-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-4a,8a-dihydro-4H-pyrano[3,2-d][1,3]dioxin-6-one
• CAS: 151830-90-9
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: HWVZYMUOGJAGRS-ZGKBOVNRSA-N

物化性质

• 沸点：
  483.3±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone 在 溶剂黄146 作用下， 反应 2.0h， 以89%的产率得到哥纳香三醇
  参考文献：
  名称：

  Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol

  摘要：

  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.

  DOI：

  10.1021/jo00115a030
• 作为产物：
  描述：

  (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one 在 对甲苯磺酸 、 丙酮 作用下， 反应 96.0h， 以67%的产率得到4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone
  参考文献：
  名称：

  Chen, Wei-Ping; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1999, # 2, p. 103 - 105

  摘要：

  DOI：

文献信息

• Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes
  作者：Lidia Dumitrescu、Doan Thi Mai Huong、Nguyen Van Hung、Benoit Crousse、Danièle Bonnet-Delpon

  DOI：10.1016/j.ejmech.2010.03.032

  日期：2010.7

  Novel fluorinated analogues of goniothalamin 1 and howiinol A 2 have been prepared from trifluorocrotonate derivatives. Trifluoromethyl goniothalamin (R/S) 4 showed a slightly lower activity than 1, while the trifluoromethyl howiinol A 16 exhibited similar activities on several cell lines in the micromolar range. Unlike (R) goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products
  作者：Wei-Shan Zhou、Zhi-Cai Yang

  DOI：10.3987/rev-96-487

  日期：——
• Chen, Wei-Ping; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1999, # 2, p. 103 - 105
  作者：Chen, Wei-Ping、Roberts, Stanley M.

  DOI：——

  日期：——
• 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.