(1S,5R)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5R)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one
• 英文别名: (1S,5R)-4-[(E)-2-(4-methoxyphenyl)ethenyl]-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: PWLJUKIPDUZZEI-YOSLTCIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5R)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one 在 吡啶 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以63%的产率得到(1R,8S)-4-(4-Methoxy-phenyl)-9,9-dimethyl-5-selena-tricyclo[6.1.1.0^2,6]deca-2(6),3-dien-7-one
  参考文献：
  名称：

  Novel Reactivity of SeO₂ with 1,3-Dienes:  Selenophene Formation

  摘要：

  A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.

  DOI：

  10.1021/jo025630t
• 作为产物：
  描述：

  马鞭草烯醇 、 4-甲氧基苯甲醛 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以98%的产率得到(1S,5R)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-one
  参考文献：
  名称：

  发现具有抗氧化和抗缺血作用的新型（1 S）-（-）-马洛酮衍生物

  摘要：

  合成了一系列带有4-苯乙烯基支架的新颖的（1 S）-（-）-马来酮衍生物。测试了合成的化合物的抗氧化，抗兴奋毒性和抗缺血活性。这些衍生物显著降低的氧气-葡萄糖剥夺诱导的神经元损伤和Ñ甲基d在皮层神经元-天冬氨酸诱发的兴奋毒性。此外，化合物3F被鉴定为在体外缺血模型有效的抗局部缺血剂，这可能是由于抑制Ñ甲基d天冬氨酸诱发的兴奋性毒性和氧化/亚硝化应激。

  DOI：

  10.1016/j.bmcl.2013.07.038

文献信息

• Pharmaceutical composition containing verbenone derivative for treating or preventing neurodegenerative disease
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US10710951B2

  公开（公告）日：2020-07-14

  The present invention relates to a pharmaceutical composition or a functional health food comprising a verbenone derivative and pharmaceutically acceptable salts thereof as active ingredients for treating or preventing a neurodegenerative disease. More specifically, the verbenone derivative according to the present invention reduces neuronal cell death and oxidative stress, and is highly effective in preventing ischemic brain damage and inflammatory cell migration in rats, thereby providing the pharmaceutical composition or the functional health food which is useful in treating neurodegenerative diseases.

  本发明涉及一种药物组合物或功能性保健食品，其中包含马鞭草酮衍生物及其药学上可接受的盐类作为活性成分，用于治疗或预防神经退行性疾病。更具体地说，根据本发明的马鞭草酮衍生物可减少神经元细胞死亡和氧化应激，对防止大鼠缺血性脑损伤和炎症细胞迁移非常有效，从而提供了有助于治疗神经退行性疾病的药物组合物或功能性保健食品。
• PHARMACEUTICAL COMPOSITION CONTAINING VERBENONE DERIVATIVE FOR TREATING OR PREVENTING NEURODEGENERATIVE DISEASE
  申请人：Korea University Research and Business Foundation

  公开号：EP2857007B1

  公开（公告）日：2018-03-28
• US9603842B2
  申请人：——

  公开号：US9603842B2

  公开（公告）日：2017-03-28
• Novel Reactivity of SeO₂ with 1,3-Dienes:  Selenophene Formation
  作者：Truc M. Nguyen、Ilia A. Guzei、Daesung Lee

  DOI：10.1021/jo025630t

  日期：2002.9.1

  A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.
• Discovery of novel (1S)-(−)-verbenone derivatives with anti-oxidant and anti-ischemic effects
  作者：Chung Ju、Sumi Song、Sunyoung Hwang、Chorong Kim、Minkyoung Kim、Jail Gu、Yu-Kyoung Oh、Kyeong Lee、Jinsun Kwon、Kiho Lee、Won-Ki Kim、Yongseok Choi

  DOI：10.1016/j.bmcl.2013.07.038

  日期：2013.10

  A series of novel (1S)-(−)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen–glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified

  合成了一系列带有4-苯乙烯基支架的新颖的（1 S）-（-）-马来酮衍生物。测试了合成的化合物的抗氧化，抗兴奋毒性和抗缺血活性。这些衍生物显著降低的氧气-葡萄糖剥夺诱导的神经元损伤和Ñ甲基d在皮层神经元-天冬氨酸诱发的兴奋毒性。此外，化合物3F被鉴定为在体外缺血模型有效的抗局部缺血剂，这可能是由于抑制Ñ甲基d天冬氨酸诱发的兴奋性毒性和氧化/亚硝化应激。