(+)-5α-hydroxy-β-selinene | 119967-73-6

• 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: (+)-5α-hydroxy-β-selinene
• 英文别名: (+)-(5R,7S,10S)-cis-Selina-4(15),11-dien-5-ol；(3R,4aR,8aR)-8a-methyl-5-methylidene-3-prop-1-en-2-yl-2,3,4,6,7,8-hexahydro-1H-naphthalen-4a-ol
• CAS: 119967-73-6
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: OEFZSVXJENLPRM-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-5α-hydroxy-β-selinene 在 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (+)-(11R)-eudesm-4(14)-en-5α,11R,12-triol
  参考文献：
  名称：

  Enantioselective total syntheses of kudtriol, 5-epi-kudtriol and their C-11 epimers

  摘要：

  Two approaches for the enantioselective syntheses of naturally occurring kudtriol 2a and 5-epi-kudtriol 3a as well as their C-ll epimers are presented, both using the Sharpless asymmetric dihydroxylation as the key reaction. Through comparison of the spectral data of natural triols and synthetic samples, we could confirm the absolute configuration of the natural triols. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00119-1
• 作为产物：
  描述：

  α-香附酮 在 dichloroalane 、 碳酸氢钠 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 (+)-5α-hydroxy-β-selinene
  参考文献：
  名称：

  Enantioselective total syntheses of kudtriol, 5-epi-kudtriol and their C-11 epimers

  摘要：

  Two approaches for the enantioselective syntheses of naturally occurring kudtriol 2a and 5-epi-kudtriol 3a as well as their C-ll epimers are presented, both using the Sharpless asymmetric dihydroxylation as the key reaction. Through comparison of the spectral data of natural triols and synthetic samples, we could confirm the absolute configuration of the natural triols. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00119-1

文献信息

• First Synthesis of (+)-5α-Hydroxy-β-selinene and (−)-5β-Hydroxy-β-selinene
  作者：Zhaoming Xiong、Gang Zhou、Yonggang Chen、Yulin Li

  DOI：10.1039/a801951g

  日期：——

  A facile and efficient synthesis of (+)-5α-hydroxy-β-selinene 1 and (–)-5β-hydroxy-β-selinene 2 starting from (+)-dihydrocarvone has been carried out.

  以(+)-二氢香芹酮为起点，简便高效地合成了(+)-5δ-±-羟基-δ-硒烯 1 和(â)-5δ-²-羟基-δ-硒烯 2。
• Terpenoids from the seeds of Artemisia annua
  作者：Geoffrey D. Brown、Guang-Yi Liang、Lai-King Sy

  DOI：10.1016/s0031-9422(03)00294-2

  日期：2003.9

  sesquiterpenes, three monoterpenes and one diterpene natural product have been isolated from the seeds of Artemisia annua. The possible biogenesis of some of these natural products are discussed by reference to recently reported experimental results for the autoxidation of dihydroartemisinic acid and other terpenoids from Artemisia annua.

  已从青蒿种子中分离出十四种倍半萜、三种单萜和一种二萜天然产物。参考最近报道的二氢青蒿酸和青蒿中其他萜类化合物的自氧化实验结果，讨论了其中一些天然产物的可能生物起源。
• Enantioselective total syntheses of kudtriol, 5-epi-kudtriol and their C-11 epimers
  作者：Gang Zhou、Xiaolei Gao、Zhe Zhang、Weidong Z Li、Yulin Li

  DOI：10.1016/s0957-4166(00)00119-1

  日期：2000.5

  Two approaches for the enantioselective syntheses of naturally occurring kudtriol 2a and 5-epi-kudtriol 3a as well as their C-ll epimers are presented, both using the Sharpless asymmetric dihydroxylation as the key reaction. Through comparison of the spectral data of natural triols and synthetic samples, we could confirm the absolute configuration of the natural triols. (C) 2000 Elsevier Science Ltd. All rights reserved.