(1R,2S,11S,12S,16R)-2-phenyl-10,13,17-trioxatetracyclo[9.6.0.03,8.012,16]heptadeca-3,5,7-trien-14-one | 1361026-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (1R,2S,11S,12S,16R)-2-phenyl-10,13,17-trioxatetracyclo[9.6.0.03,8.012,16]heptadeca-3,5,7-trien-14-one
• CAS: 1361026-55-2
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: QCAVTTYSHUKHBB-DABHTEOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,11S,12S,16R)-2-phenyl-10,13,17-trioxatetracyclo[9.6.0.03,8.012,16]heptadeca-3,5,7-trien-14-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 192.0h， 以70%的产率得到(2R,3S,3aR,6aR)-3-hydroxy-2-[(S)-(2-methylphenyl)-phenylmethyl]-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
  参考文献：
  名称：

  Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies

  摘要：

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.069
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 吡啶 、 四氟化钛 、 高碘酸 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 428.0h， 生成 (1R,2S,11S,12S,16R)-2-phenyl-10,13,17-trioxatetracyclo[9.6.0.03,8.012,16]heptadeca-3,5,7-trien-14-one
  参考文献：
  名称：

  Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies

  摘要：

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.069

文献信息

• Novel goniofufurone and 7-epi-goniofufurone mimics from an unexpected titanium-mediated displacement process
  作者：Jovana Francuz、Bojana Srećo、Mirjana Popsavin、Goran Benedeković、Vladimir Divjaković、Vesna Kojić、Gordana Bogdanović、Agneš Kapor、Velimir Popsavin

  DOI：10.1016/j.tetlet.2012.01.121

  日期：2012.4

  Treatment of 7-O-benzoyl-5-O-benzyl derivatives of (+)-goniofufurone or 7-epi-(+)-goniofufurone with titanium(IV) chloride or titanium(IV) bromide gave 7-chloro and 7-bromo-7-deoxy-goniofufurone mimics as the main reaction products along with minor amounts of the corresponding C-7 epimers. An unexpected cyclized product, benzoxepane 8 was isolated in some cases. (C) 2012 Elsevier Ltd. All rights reserved.
• Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies
  作者：Velimir Popsavin、Jovana Francuz、Bojana Srećo Zelenović、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.bmcl.2013.08.069

  日期：2013.10

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.