(S)-(+)-2,6-dimethyl-5-heptenal | 118333-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-2,6-dimethyl-5-heptenal
• 英文别名: (S)-2,6-dimethyl-5-heptenal；S-(-)-citronellal；(S)-2,6-dimethylhept-5-enal；(2S)-2,6-dimethylhept-5-enal
• CAS: 118333-87-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: YGFGZTXGYTUXBA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (S)-(+)-2,6-dimethyl-5-heptenal 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以48.1%的产率得到(S)-(+)-2,6-dimethyl-5-heptenoic acid
  参考文献：
  名称：

  摘要：

  Usinggas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, butanoic acid, skatole, and (E)-2,6-dimethyl-6-octen-2-ol were identified as constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper subaeneus, which reproducibly elicited EAD responses in male and female antennae. This is the first report of the occurrence of (E)-2,6-dimethyl-6-octen-2-ol as a natural product, for which the name (E)-subaeneol is proposed. In some experiments, a few other constituents of the secretion also gave reproducible responses in specific male and female antennae but did not elicit responses when the analyses were repeated with other antennae. The major volatile constituent of the secretion, identified as (S)-(C)-2,6-dimethyl-5-heptenoic acid, is one of these EAD-active compounds. Both this compound and (E)-2,6-dimethyl-6-octen-2-ol were synthesized from authentic starting materials for comparison with the natural products.

  DOI：

  10.1023/a:1021440220329
• 作为产物：
  描述：

  (2S)-2,6-dimethyl-5-hepten-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到(S)-(+)-2,6-dimethyl-5-heptenal
  参考文献：
  名称：

  Odinokov, V. N.; Kukovinets, O. S.; Kasradze, V. G., Russian Journal of Organic Chemistry, 1993, vol. 29, # 10, p. 1611 - 1615

  摘要：

  DOI：

文献信息

• Synthesis of Tetrahydronaphthyridines from Aldehydes and HARP Reagents via Radical Pictet–Spengler Reactions
  作者：Moritz K. Jackl、Imants Kreituss、Jeffrey W. Bode

  DOI：10.1021/acs.orglett.6b00523

  日期：2016.4.15

  with newly designed HARP (halogen amine radical protocol) reagents gives access to α-substituted tetrahydronaphthyridines. By using different HARP reagents, various regioisomeric structures can be prepared in a single operation. These products, which are of high value in medicinal chemistry, are formed in a predictable manner via a formal Pictet–Spengler reaction of electron-poor pyridines that would

  醛与新设计的HARP（卤素胺自由基方案）试剂的组合可使用α-取代的四氢萘啶。通过使用不同的HARP试剂，可以在一次操作中制备各种区域异构结构。这些产品在药物化学中具有很高的价值，它们是通过可预测的方式通过贫电子吡啶的正式Pictet-Spengler反应形成的，而该不良电子吡啶不会参与相应的极性反应。
• Total Synthesis of (−)-Stellettamide B and Determination of Its Absolute Stereochemistry
  作者：Naoki Yamazaki、Wataru Dokoshi、Chihiro Kibayashi

  DOI：10.1021/ol0003228

  日期：2001.1.1

  [figure: see text] The first total synthesis of (-)-stellettamide B has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)-indolizidine fragment, prepared by TiCl4-mediated asymmetric allylation of the tricyclic N-acyl-N,O-acetal, with the chiral trienoic acid fragment. This synthesis led to revision of the published relative stereochemistry of the natural product and established

  [图：见正文]（-）-stellettamide B的第一个全合成是通过基于手性1-（氨基甲基）-吲哚并咪唑片段的酰胺偶联的序列实现的，该序列是由TiCl4介导的三环N的不对称烯丙基化制备的-酰基-N，O-乙缩醛，带有手性三烯酸片段。该合成导致对天然产物的公开相对立体化学的修订，并将其绝对立体化学确定为1S，4S，8aR，6” R。
• Increased Felkin−Anh Selectivity Using AlMe₃ in the Addition of Vinyllithiums to α-Chiral Aldehydes:  Do “Ate” Complexes Play Any Role?
  作者：Claude Spino、Marie-Claude Granger、Marie-Claude Tremblay

  DOI：10.1021/ol027236n

  日期：2002.12.1

  [GRAPHICS]AlMe3 dramatically increases the diastereoselectivity of addition of vinyllithiums to alpha-chiral aldehydes but decreases that of methyllithium. Our results are explained in terms of an addition of the free vinyllithium on the Me3Al-aldehyde complex.
• KULICKE, KLAUS JURGEN;GIESE, BERND, SYNLETT.,(1990) N, C. 91-92
  作者：KULICKE, KLAUS JURGEN、GIESE, BERND

  DOI：——

  日期：——
• PROCESS FOR PRODUCING 2,6-DIMETHYL-5-HEPTEN-1-AL
  申请人：BASF SE

  公开号：EP3140272A1

  公开（公告）日：2017-03-15