(R)-2,5-dimethylhex-4-enal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2,5-dimethylhex-4-enal
• 英文别名: 2,5-dimethyl-4-hexenal；(2R)-2,5-dimethylhex-4-enal
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: NTPNJYFKMSTHQR-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-2,5-dimethylhex-4-enal 在 戴斯-马丁氧化剂 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (R)-3,6-dimethyl-5-hepten-2-one
  参考文献：
  名称：

  Syntheses and odor properties of optically active dimethyl octenone and its analogs

  摘要：

  The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.002
• 作为产物：
  描述：

  (3-甲基丁-2-烯基)丙二酸二乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 Amano PS Lipase 、 水 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 异丙醚 为溶剂， 反应 19.0h， 生成 (R)-2,5-dimethylhex-4-enal
  参考文献：
  名称：

  Syntheses and odor properties of optically active dimethyl octenone and its analogs

  摘要：

  The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.002

文献信息

• ——
  作者：Claudia M. Schulz、Lutz Lehmann、Rumsaïs Blatrix、Pierre Jaisson、Abraham Hefetz、Wittko Francke

  DOI：10.1023/a:1021492204400

  日期：——

  Extracts of Dufour's gland of the ponerine ant, Gnamptogenys striatula, were analyzed by using the combination of gas chromatography and mass spectrometry. Series of esters of the new homoterpenoids (2E,6)-3,4,7-trimethyl-2,6-octadiene-1-ol (4-methylgeraniol) and (2E,6)-3,4,7-trimethyl-2,6-nonadiene-1-ol (bishomogeraniol) with unbranched medium-chain fatty acids were identified. Transformation of the

  通过使用气相色谱法和质谱法相结合的方法对杜弗氏蚂蚁腺体Gnamptogenys striatula的提取物进行了分析。新的类萜类化合物（2E，6）-3,4,7-三甲基-2,6-辛二烯-1-醇（4-甲基香叶醇）和（2E，6）-3,4,7-三甲基-鉴定了具有直链中链脂肪酸的2，6-壬二烯-1-醇（双香叶香叶醇）。手性天然产物向1,4-二（三氟乙酰氧基）-3-甲基戊烷的转化以及在修饰的环糊精相上的气相色谱保留时间与合成旋光参考样品的气相色谱保留时间的比较证明，立体中心可以保持（S）-组态。萃取物中的（2E，4S，6）-3,4,7-三甲基-2,6-辛二烯-1-基酯和相应的十二烷酸酯是主要的挥发物。
• Syntheses and odor properties of optically active dimethyl octenone and its analogs
  作者：Masashi Kawasaki、Momo Shimizu、Saki Kuroyanagi、Yoshiaki Shishido、Tsuyoshi Komiyama、Naoki Toyooka

  DOI：10.1016/j.tetasy.2016.02.002

  日期：2016.4

  The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported. (C) 2016 Elsevier Ltd. All rights reserved.