(E)-8-chloro-2,6-dimethyl-octa-2,6-dien-4-one | 79998-86-0

• 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
• 英文名称: (E)-8-chloro-2,6-dimethyl-octa-2,6-dien-4-one
• 英文别名: 5-oxo-geranyl chloride；(6E)-8-chloro-2,6-dimethylocta-2,6-dien-4-one
• CAS: 79998-86-0
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: PJHZWBVDRGLZMX-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 在 sodium tetrahydroborate 、 pyridinium chlorochromate absorbed on neutral alumina 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.25h， 生成 Methyl 4[(2e)-3,7-dimethyl-5-oxo-2,6-octadienyl]oxy-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis of Geranyl Phenyl Ethers Based on the Cytotoxic Monoterpenoids from the Liverwort Genus Trichocolea

  摘要：

  The synthesis of three geranyl ethers, methyl 4-[{(2E)-3,7-dimethyl-5-oxo-2,6-octadienyl}oxy]-3-methoxybenzoate (1), methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxybenzoate (2), and methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-hydroxybenzoate (3), previously isolated from New Zealand Trichocolea liverworts, is described. Differing reactivity of the hydroxy groups of methyl protocatachuate toward alkylation and the ability of alkyl groups to migrate from oxygen to an ortho-oxygen in these benzene derivatives are noted.

  DOI：

  10.1021/np980031w
• 作为产物：
  描述：

  3-甲基巴豆酰氯 、 天然橡胶 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(E)-8-chloro-2,6-dimethyl-octa-2,6-dien-4-one
  参考文献：
  名称：

  新的草烯衍生物的合成；（2E，6E，9E）-和（2Z，6E，9E）-环戊二烯酮，通过被保护的氰醇的分子内烷基化。通往腐殖质的途径

  摘要：

  （2 E，6 E，9 E）-2,5,5,9-tetramethyl-2,6,9-cyclooundecatrienone（）和（2 Z，6 E，9 E）-2,5,5，提出了基于受保护的氰醇分子内烷基化的9-四甲基-2,6,9-环烯基三烯酮（）和（E，E，E）-三烯酮向humulene（）的转化。

  DOI：

  10.1016/s0040-4039(00)86230-9

文献信息

• Narcissus trevithian and Narcissus geranium: Analysis and synthesis of compounds
  作者：Hans M. van Dort、Paul P. Jagers、Roel. ter Heide、Anton J. A. van der Weerdt

  DOI：10.1021/jf00035a047

  日期：1993.11

  The essential oils of two narcissus varieties, Narcissus trevithian and Narcissus geranium, obtained by extraction of flowers followed by high vacuum distillation of the absolute, were analyzed by GC/MS. After separation in fractions, unknown compounds were isolated by preparative GLC and their structures established by NMR/IR spectroscopy. The synthesis of a number of new compounds, found for the first time in narcissus oil, is described. The two narcissus species are compared with respect to their main components and odor quality. All compounds found so far in narcissus varieties are listed.
• TAKAHASHI, TAKASHI;KITAMURA, KYOKO;TSUJI, J., TETRAHEDRON LETT., 1983, 24, N 43, 4695-4698
  作者：TAKAHASHI, TAKASHI、KITAMURA, KYOKO、TSUJI, J.

  DOI：——

  日期：——
• Synthesis of Geranyl Phenyl Ethers Based on the Cytotoxic Monoterpenoids from the Liverwort Genus <i>Trichocolea</i>
  作者：Seung-Hwa Baek、Nigel B. Perry、Rex T. Weavers

  DOI：10.1021/np980031w

  日期：1998.9.1

  The synthesis of three geranyl ethers, methyl 4-[(2E)-3,7-dimethyl-5-oxo-2,6-octadienyl}oxy]-3-methoxybenzoate (1), methyl 4-[(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxybenzoate (2), and methyl 4-[(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-hydroxybenzoate (3), previously isolated from New Zealand Trichocolea liverworts, is described. Differing reactivity of the hydroxy groups of methyl protocatachuate toward alkylation and the ability of alkyl groups to migrate from oxygen to an ortho-oxygen in these benzene derivatives are noted.
• Syntheses of new humulene derivatives; (2E,6E,9E)- and (2Z,6E,9E)-cycloundecatrienones, by intramolecular alkylation of protected cyanohydrin. A route to humulene
  作者：Takashi Takahashi、Kyoko Kitamura、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)86230-9

  日期：——

  6,9-cycloundecatrienone () and (2Z,6E,9E)-2,5,5,9-tetramethyl-2,6,9-cycloundecatrienone () based on the intramolecular alkylation of protected cyanohydrin and conversion of the (E,E,E)-trienone to humulene () are presented.

  （2 E，6 E，9 E）-2,5,5,9-tetramethyl-2,6,9-cyclooundecatrienone（）和（2 Z，6 E，9 E）-2,5,5，提出了基于受保护的氰醇分子内烷基化的9-四甲基-2,6,9-环烯基三烯酮（）和（E，E，E）-三烯酮向humulene（）的转化。