(5Z)-2-甲基-6-(4-甲基-3-环己烯-1-基)-2,5-庚二烯-4-酮 | 26294-59-7

• 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
• 中文名称: (5Z)-2-甲基-6-(4-甲基-3-环己烯-1-基)-2,5-庚二烯-4-酮
• 英文名称: (E)-α-atlantone
• 英文别名: α-atlantone；(E)-atlantone；alpha-Atlantone；(5E)-2-methyl-6-[(1R)-4-methylcyclohex-3-en-1-yl]hepta-2,5-dien-4-one
• CAS: 26294-59-7
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: OJEFBZMKKJTKKK-UELRPHRMSA-N

物化性质

• 沸点：
  321.1±21.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (5Z)-2-甲基-6-(4-甲基-3-环己烯-1-基)-2,5-庚二烯-4-酮 在 palladium on activated charcoal 作用下， 反应 12.0h， 以80%的产率得到dihydro-ar-turmerone
  参考文献：
  名称：

  Aromatization of (Z) and (E)-α-atlantones isolated from Cedrus atlantica essential oil followed by condensation with thiosemicarbazide: synthesis of new thiadiazolines derivatives

  摘要：

  Aromatization, using Pd/C (10%) of (Z) and (E)-alpha-atlantones isolated from Cedrus atlantica essential oil, followed by condensation with thiosemicarbazide gave novel 1,3,4-thiadiazolic derivatives by the introduction of new functional groups on the terpenic skeletons. After aromatization and thiosemicarbazide condensation, all products were obtained in good yields to give thiadiazolic compounds bearing new spiro carbons. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.103
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 aluminum oxide 作用下， 以 乙醚 为溶剂， 生成 (5Z)-2-甲基-6-(4-甲基-3-环己烯-1-基)-2,5-庚二烯-4-酮
  参考文献：
  名称：

  Metalation of limonene. Novel method for the synthesis of bisabolane sesquiterpenes

  摘要：

  DOI：

  10.1021/ja00767a044

文献信息

• Studies in sesquiterpenes—LIII
  作者：R. Shankaranarayan、S. Krishnappa、S.C. Bisarya、Sukh Dev

  DOI：10.1016/0040-4020(77)80415-8

  日期：——

  tetrahydro-γ-pyrone from the essential oil from the wood of Cedrus deodara Loud is described. The compound, which has been named deodarone, has been chemically correlated with the sesquiterpene ketone, atlantone. An hydroxy ketone, designated as atlantolone, has also been isolated. This compound appears to be the precursor of the new C12-ketone, recently described as a component of the essential oil of Cedrus atlantica

  描述了一种从雪松木的香精油中分离出新的基于双杂草烷的四氢-γ-吡喃酮并进行结构测定的方法。该化合物已被命名为Deodarone，已与倍半萜酮，Atlantone化学相关。还分离出了称为酮兰酮的羟基酮。该化合物似乎是新的C 12-酮的前体，最近被描述为Cedrus atlantica Manet香精油的一种成分。
• [2+1] Cycloaddition reaction of α-atlantone with m-CPBA in the light of experimental and MEDT quantum-chemical study
  作者：Houria Raji、Abdelhak Ouled Aitouna、Ali Barhoumi、Redouane Hammal、Ahmed Chekroun、Abdellah Zeroual、Ahmed Benharref、Noureddine Mazoir

  DOI：10.1007/s10593-023-03172-4

  日期：2023.3

  diastereoisomers of 6-(3,4-epoxy-4-methylcyclohexyl)-2-methylhepta-2,5-dien-4-one were synthesized in the [2+1] cycloaddition reaction of α-atlantone, isolated compound from Cedrus atlantica essential oil, with m-chloroperbenzoic acid in CH2Cl2. The chemoselectivity of this cycloaddition reaction has been both experimentally and theoretically studied within the molecular electron density theory. Parr functions

  6-(3,4-epoxy-4-methylcyclohexyl)-2-methylhepta-2,5-dien-4-one 的两种非对映异构体是在 α-atlantone 的 [2+1] 环加成反应中合成的，从大西洋雪松精油，在 CH 2 Cl 2中含有间氯过苯甲酸。这种环加成反应的化学选择性已经在分子电子密度理论中进行了实验和理论研究。试剂的 Parr 函数和电子定位函数分析正确预测了实验化学选择性，在 C3'=C4' 键处具有最有利的相互作用。这些反应遵循两阶段一步机制。
• Plattier; Teisseire, Recherches, 1974, vol. 19, p. 153,164
  作者：Plattier、Teisseire

  DOI：——

  日期：——
• Vilsmeier Formylation of Limonene. A New Method for the Synthesis of α-Atlantone
  作者：G. Dauphin

  DOI：10.1055/s-1979-28835

  日期：——
• Metalation of limonene. Novel method for the synthesis of bisabolane sesquiterpenes
  作者：Robert J. Crawford、William F. Erman、Charles D. Broaddus

  DOI：10.1021/ja00767a044

  日期：1972.6