filbertone | 122440-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: filbertone
• 英文别名: (E,5S)-5-methylhept-2-en-4-one
• CAS: 122440-59-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: ARJWAURHQDJJAC-KNIZRNDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(4-氟苯乙基磺酰基)-1-苯基-1H-四唑e 、 filbertone 在 4-二甲氨基吡啶 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以52%的产率得到2-[(4-fluorophenethyl)sulfonyl]-5-methylheptan-4-one
  参考文献：
  名称：

  Photoredox Generation of Sulfonyl Radicals and Coupling with Electron Deficient Olefins

  摘要：

  Various sulfone tetrazoles were activated via iridium photoredox catalysis in the presence of DMAP to give diallcyl sulfones. The presumed sulfone radical intermediates were trapped by a range of electron-deficient olefins in generally good to excellent yields.

  DOI：

  10.1021/acs.orglett.0c01730
• 作为产物：
  描述：

  (S)-2-甲基丁醛 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 三聚丙烯 、 丙二烯 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 24.0h， 生成 filbertone
  参考文献：
  名称：

  Improved synthesis of(S, E)-(+)-5-methylhept-2-en-4-one, the major aroma compound of hazelnuts

  摘要：

  An improved synthesis of enantiomerically pure (S, E)-(+)-5-methylhept-2-en-4-one from (S)-(+)-2-methyl-1-butanol in four steps is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00534-7

文献信息

• Scalable Preparation of Enantioenriched (S)-5-methylhept-2-en-4-one. Synthesis and Aroma Properties of Achiral Analogues Thereof
  作者：Eva Puchľová、Michal Dendys、Ivan Špánik、Peter Szolcsányi

  DOI：10.3390/molecules24244497

  日期：——

  addition, we have designed and prepared a set of new (di)enones as achiral synthetic analogues of the title compound. The results of their sensory analyses clearly show that relatively minor structural changes of the natural molecule significantly alter its olfactory properties. Thus, simple (poly)methylation completely changes the original hazelnut aroma of (S)-5-methylhept-2-en-4-one and shifts the

  (S)-5-Methylhept-2-en-4-one 是榛子中的一种关键风味化合物。我们已经以 39% 的总产率 (73% ee) 进行了基于手性池的化学酶合成。基于羟醛的四步序列避免使用高反应性和/或有毒试剂，不需要无水条件，仅使用蒸馏作为纯化方法。因此，这种方法代表了一种绿色且可扩展的替代方案，可替代迄今为止已知的针对这种天然产物的两种立体选择性方法。此外，我们设计并制备了一组新的（二）烯酮作为标题化合物的非手性合成类似物。他们的感官分析结果清楚地表明，天然分子相对较小的结构变化会显着改变其嗅觉特性。因此，
• Jauch, Johann; Schmalzing, Dieter; Schurig, Volker, Angewandte Chemie, 1989, vol. 101, # 8, p. 1039 - 1041
  作者：Jauch, Johann、Schmalzing, Dieter、Schurig, Volker、Emberger, Roland、Hopp, Rudolf、et al.

  DOI：——

  日期：——
• JAUCH, JOHANN;SCHMALZING, DIETER;SCHURIG, VOLKER;EMBERGER, ROLAND;HOPP, R+, ANGEW. CHEM., 101,(1989) N, C. 1039-1041
  作者：JAUCH, JOHANN、SCHMALZING, DIETER、SCHURIG, VOLKER、EMBERGER, ROLAND、HOPP, R+

  DOI：——

  日期：——
• MICHAEL ADDITION PRODUCT AND SCHIFF'S BASE AROMACHEMICALS
  申请人：Flexitral, Inc.

  公开号：EP1851211A2

  公开（公告）日：2007-11-07
• Michael addition product and Schiff's base aromachemicals
  申请人：Turin Luca

  公开号：US20060204462A1

  公开（公告）日：2006-09-14

  A pro-odorant or pro-flavorant having the formula (I): wherein R 1 is H, an aliphatic group or an aromatic group, R 2 is an aliphatic group or an aromatic group, provided that the total number of carbon atoms in the groups R 1 and R 2 is 10 or more; R 3 , R 4 and R 6 are each independently hydrogen or organic moieties which together with C(O)R 5 render a compound of formula R 5 C(O)R 6 C=CR 3 R 4 a material having odorant or flavourant characteristics and R 5 is hydrogen or an organic moiety; or having the formula (II): R 8 R 9 C=NR 10 wherein R 10 is an aliphatic group or an aromatic group having at least 10 carbon atoms; R 8 and R 9 are each independently hydrogen or organic moieties which together with C=O render a compound of formula R 8 R 9 C=O a material having odorant or flavourant characteristics, provided that only one of R 8 and R 9 is hydrogen; or having the formula (III): wherein R 1 is H, an aliphatic group or an aromatic group, R 2 is an aliphatic group or an aromatic group, provided that the total number of carbon atoms in the groups R 1 and R 2 is 10 or more; Z is CH 2 or O, n is 0 or 1, such that the ring is a 5 or 6 membered ring, R 11 is alkyl or alkenyl having up to 10 carbon atoms so as to render a compound of formula