L-α-Curcumen | 4548-25-8

• 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: L-α-Curcumen
• 英文别名: 1-methyl-4-[(2R)-6-methylhept-6-en-2-yl]benzene
• CAS: 4548-25-8
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: BVFXTXVUDRHULL-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  methyl (R)-5-(4-methylphenyl)hexanoate 在 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 L-α-Curcumen 、 alpha-姜黄烯
  参考文献：
  名称：

  内酯的立体有择氢解：应用的全合成（- [R ）-芳-Himachalene和（- [R）-Curcumene

  摘要：

  对于和姜黄的合成的直接战略AR-报道himachalene。合成的亮点包括使用Pd / C或Ni / Raney催化剂的催化和不对称乙烯基Mukaiyama反应和叔苄基中心的立体有择氢解。值得注意的是，使用Ni / Raney，氢解的立体选择性结果（转化相对于保留）取决于叔苄醇的取代。

  DOI：

  10.1021/acs.joc.7b00419

文献信息

• Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies
  作者：Petra M. Bleeker、Paul J. Diergaarde、Kai Ament、Stefan Schütz、Bettina Johne、Jan Dijkink、Henk Hiemstra、René de Gelder、Michiel T.J. de Both、Maurice W. Sabelis、Michel A. Haring、Robert C. Schuurink

  DOI：10.1016/j.phytochem.2010.10.014

  日期：2011.1

  How whiteflies (Bemisia tabaci) make the choice for a host plant prior to landing, is not precisely known. Here we investigated whether they respond to specific volatiles of tomato. Zingiberene and curcumene were purified from Solanum habrochaites (PI127826), characterised by NMR and X-ray analysis and identified as 7-epizingiberene and R-curcumene. In contrast, oil from Zingiber officinalis contained the stereoisomers zingiberene and S-curcumene, respectively. Using a combination of free-choice bio-assays and electroantennography, 7-epizingiberene and its dehydrogenated derivative R-curcumene were shown to be active as semiochemicals to B. tabaci adults, whereas the stereoisomers from ginger were not. In addition, R-curcumene elicited the strongest electroantennographic response. Bio-assays showed that a cultivated tomato could be made less attractive to B. tabaci than its neighbouring siblings by the addition of the tomato stereoisomer 7-epizingiberene or its derivative R-curcumene. These sesquiterpenes apparently repel adult whiteflies prior to landing, presumably because it informs them that after landing they, or their offspring, may be exposed to higher and lethal concentrations of the same compounds. (C) 2010 Elsevier Ltd. All rights reserved.