5-hydroxy-4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone | 138531-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-hydroxy-4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone
• 英文别名: 5-Hydroxy-4-(6-phenyl-1,3,5-hexatrienyl)-2(5H)-furanone；2-hydroxy-3-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2H-furan-5-one
• CAS: 138531-17-6
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: ASTSPPNXMWCPRE-CDWOPPGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以57%的产率得到4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone
  参考文献：
  名称：

  Biological activities of retinoidal γ-hydroxybutenolides in cancer cell apoptosis and differentiation

  摘要：

  Retinoidal gamma-hydroxybutenolides 2a-d having various lengths of conjugated double bond were prepared in three steps from the corresponding aldehyde 4. Their biological activities were then measured. Of these compounds, only compound 2c possessing a structure similar to that of retinoic acid showed differentiation- inducing activity and very strong apoptosis-inducing activity in HL-60 cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.034
• 作为产物：
  描述：

  5-triethylsilyloxy-4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone 在 氟化氢吡啶 作用下， 以72%的产率得到5-hydroxy-4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]-2(5H)-furanone
  参考文献：
  名称：

  在大块路易斯酸的存在下，采用交叉羟醛缩合法合成γ-羟基丁烯内酯及其抗肿瘤活性。

  摘要：

  使用庞大的路易斯酸三（2,6-二苯酚铝）铝，通过醛2a-d与受保护的γ-羟基-β-甲基丁烯化物3或4之间的交叉羟醛缩合反应，可以提高γ-羟基丁烯化物1a-d的合成效率（ ATPH）。使用相同的方法，合成了具有各种杂芳族环的γ-羟基丁烯内酯17a-d，并评估了它们的抗肿瘤活性。

  DOI：

  10.1248/cpb.55.1365

文献信息

• JPH04316568A
  申请人：——

  公开号：JPH04316568A

  公开（公告）日：1992-11-06
• Biological activities of retinoidal γ-hydroxybutenolides in cancer cell apoptosis and differentiation
  作者：Yumiko Yamano、Yukari Mizuguchi、Yumi Fujita、Maki Yoshida、Masayoshi Ito、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2005.07.034

  日期：2005.11

  Retinoidal gamma-hydroxybutenolides 2a-d having various lengths of conjugated double bond were prepared in three steps from the corresponding aldehyde 4. Their biological activities were then measured. Of these compounds, only compound 2c possessing a structure similar to that of retinoic acid showed differentiation- inducing activity and very strong apoptosis-inducing activity in HL-60 cells. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of .GAMMA.-Hydroxybutenolides Applying Crossed Aldol Condensation in the Presence of a Bulky Lewis Acid and Their Anti-tumor Activity
  作者：Yumiko Yamano、Yumi Fujita、Yukari Mizuguchi、Kimie Nakagawa、Toshio Okano、Masayoshi Ito、Akimori Wada

  DOI：10.1248/cpb.55.1365

  日期：——

  An improved synthesis of gamma-hydroxybutenolides 1a-d was achieved via crossed aldol condensation between aldehydes 2a-d and the protected gamma-hydroxy-beta-methylbutenolides 3 or 4 using the bulky Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH). Using this same methodology, the gamma-hydroxybutenolides 17a-d having various heteroaromatic rings were synthesized and their anti-tumor activities

  使用庞大的路易斯酸三（2,6-二苯酚铝）铝，通过醛2a-d与受保护的γ-羟基-β-甲基丁烯化物3或4之间的交叉羟醛缩合反应，可以提高γ-羟基丁烯化物1a-d的合成效率（ ATPH）。使用相同的方法，合成了具有各种杂芳族环的γ-羟基丁烯内酯17a-d，并评估了它们的抗肿瘤活性。