(E)-6,6,9-trimethyl-3,8-decadien-2-one | 210752-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6,6,9-trimethyl-3,8-decadien-2-one
• 英文别名: (3E)-6,6,9-trimethyldeca-3,8-dien-2-one
• CAS: 210752-20-8
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: DEMQDCUYWABUOE-VOTSOKGWSA-N

物化性质

• 沸点：
  280.9±19.0 °C(Predicted)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 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：

  (E)-6,6,9-trimethyl-3,8-decadien-2-one 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以66%的产率得到2-isopropyl-1-(2-oxopropylidene)-4,4-dimethylcyclopentane
  参考文献：
  名称：

  Synthetic Studies towards Compounds Related to Sterpurene and Protoilludene.

  摘要：

  As part of synthetic strategies towards the sesquiterpenes 6-protoilludene and sterpurene the intramolecular aldol condensation of 1-(2-oxopropyl)-2-acetyl-4,4-dimethylcyclopentane was studied in detail. Mixtures of 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one and 4,8,8-trimethylbicyclo[4.3.0]-3-nonen-2-one were formed. The reaction was carried out under different acidic and basic conditions, giving the two compounds in ratios varying from 1:1 to 12:1. The best conditons were found to be methanesulfonic acid in methanol. The preparation of trans-5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one by our route in about 70% overall yield constitutes formally a new synthesis of sterpurene.

  DOI：

  10.3891/acta.chem.scand.52-0806
• 作为产物：
  描述：

  3,3,6-trimethyl-5-heptenal 、 1-三苯基膦-2-丙酮 以 苯 为溶剂， 反应 52.0h， 以83%的产率得到(E)-6,6,9-trimethyl-3,8-decadien-2-one
  参考文献：
  名称：

  Synthetic Studies towards Compounds Related to Sterpurene and Protoilludene.

  摘要：

  As part of synthetic strategies towards the sesquiterpenes 6-protoilludene and sterpurene the intramolecular aldol condensation of 1-(2-oxopropyl)-2-acetyl-4,4-dimethylcyclopentane was studied in detail. Mixtures of 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one and 4,8,8-trimethylbicyclo[4.3.0]-3-nonen-2-one were formed. The reaction was carried out under different acidic and basic conditions, giving the two compounds in ratios varying from 1:1 to 12:1. The best conditons were found to be methanesulfonic acid in methanol. The preparation of trans-5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one by our route in about 70% overall yield constitutes formally a new synthesis of sterpurene.

  DOI：

  10.3891/acta.chem.scand.52-0806

文献信息

• Synthetic Studies towards Delta6-Protoilludene. A Formal Synthesis.
  作者：Trond Vidar Hansen、Stephen M'dachi、Lars Skattebøl、Yngve Stenstrøm

  DOI：10.3891/acta.chem.scand.52-1373

  日期：——

  A synthetic strategy towards Delta(6)-protoilludene included an intramolecular allene-ene cycloaddition reaction as a key step; however, the thermal reaction furnished a stereoisomeric mixture of 9-methyl-1,4,4,8-tetramethyltricyclo[6.2.0.0(2,6)]decane, which has a ring assembly isomeric with that of the target molecule. Another approach to Delta(6)-protoilludene required cis-4,4-dimethyl-2-isopropenylcyclopentylacetic acid, which was obtained from the mixture of stereoisomers by column chromatographic separation of the corresponding iodolactones. The cis-acid was further converted into cis-ethyl 4-(2-isopropenyl-4,4-dimethylcyclopentyl)-3-methyl-2-butenoate which has previously been transformed by others into Delta(6)-protoilludene. Hence, our approach constitutes formally a new synthesis of Delta(6)-protoilludene.