5-甲基-1-(4-甲基环己-3-烯-1-基)己-4-烯-1-酮 | 76280-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲基-1-(4-甲基环己-3-烯-1-基)己-4-烯-1-酮
• 英文名称: 2-methyl-6-keto-6-(4-methyl-3-cyclohexen-1-yl)-2-hexene
• 英文别名: 2-methyl-6-keto-6-(4-methyl-3-cyclohex-1-yl)-2-hexene；norbisabolenone；(+/-)-2-Methyl-6-keto-(4'-methyl-Δ^3'-cyclohexenyl)-Δ²-hexen；5-Methyl-1-(4-methyl-cyclohex-3-enyl)-hex-4-en-1-on；5-Methyl-1-(4-methyl-3-cyclohexenyl)-4-hexen-1-on；5-Methyl-1-(4-methyl-3-cyclohexen-1-yl)-4-hexen-1-one；5-methyl-1-(4-methylcyclohex-3-en-1-yl)hex-4-en-1-one
• CAS: 76280-88-1
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: BUSKKOPCEZGTQK-UHFFFAOYSA-N

物化性质

• 沸点：
  157 °C(Press: 14 Torr)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  5-甲基-1-(4-甲基环己-3-烯-1-基)己-4-烯-1-酮 、 甲基溴化镁 以 乙醚 为溶剂， 反应 3.0h， 以75%的产率得到bisabolol
  参考文献：
  名称：

  有机硅化合物的化学—165：2-三甲基甲硅烷基-甲基-1，3-丁二烯—萜烯合成的通用组成部分

  摘要：

  讨论了2-三甲基甲硅烷基甲基-1,3-丁二烯（7）的两种合成上有用的反应。7与路易斯酸活化的酰基氯，醛，酮和乙缩醛的反应生成异戊二烯基化的化合物，而7与亲二烯体进行Diels-Alder反应。该反应的高区域特异性使7成为萜烯合成的通用组成部分。

  DOI：

  10.1016/s0040-4020(01)88587-2
• 作为产物：
  描述：

  (R)-2-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxolane 在 盐酸 、 potassium tert-butylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 、 苯 为溶剂， 生成 5-甲基-1-(4-甲基环己-3-烯-1-基)己-4-烯-1-酮
  参考文献：
  名称：

  Vig,O.P. et al., Journal of the Indian Chemical Society, 1966, vol. 43, p. 27 - 31

  摘要：

  DOI：

文献信息

• Regioselective α-Alkylation of Silyl Enolates using a Mild Catalyst- ZnCl₂Doped on Acidic Alumina
  作者：G. L. Kad、Vasundhara Singh、Anupam Khurana、Sangeeta Chaudhary、Jasvinder Singh

  DOI：10.1080/00397919908085973

  日期：1999.10

  Abstract ZnCl2 doped acidic alumina used as a solid support acts as a better Lewis acid in the SNl reaction of trimethyl silyl enol ethers with 30, allylic and benzylic halides to yield exclusively the substituted product in excellent yields. This method has been employed for the synthesis of monocyclic sesquitepene hydrocarbon, (±)-β-bisabolene and a monoterpene, 2,6-dimethyl-7-octen-4-one.

  摘要 ZnCl2 掺杂的酸性氧化铝用作固体载体，在三甲基甲硅烷基烯醇醚与 30、烯丙基和苄基卤化物的 SNl 反应中充当更好的路易斯酸，以优异的产率专门产生取代产物。该方法已被用于合成单环倍半萜烃、(±)-β-红没药烯和单萜、2,6-二甲基-7-辛烯-4-one。
• Highly regioselective diels-alder reactions of 2-trimethylsilylmethyl- 1,3-butadiene catalyzed by a lewis acid and applications to syntheses of terpenes
  作者：Akira Hosomi、Hirokazu Iguchi、Jun-ichi Sasaki、Hideki Sakurai

  DOI：10.1016/s0040-4039(00)86886-0

  日期：1982.1

  2-Trimethylsilylmethyl-1,3-butadiene undergoes highly regioselective Diels-Alder reactions with dienophiles such as acrolein and methyl vinyl ketone catalyzed by aluminum chloride in which the “para” isomers are obtained almost exclusively. The adducts are converted readily to a variety of naturally occurring mono and sesquiterpenes.

  2-三甲基甲硅烷基甲基-1,3-丁二烯与亲二烯（如丙烯醛和甲基乙烯基酮）通过氯化铝催化发生高度区域选择性的Diels-Alder反应，其中几乎完全获得“对”异构体。加合物易于转化为各种天然存在的单倍体和倍半萜。
• Termite Trail Attractants: New Syntheses of Racemic (<i>E</i>)-<i>α</i>-, (<i>Z</i>)-<i>α</i>- and<i>β</i>-Bisabolenes
  作者：Laura Argenti、Fabio Bellina、Adriano Carpita、Nicola Dell'Amico、Renzo Rossi

  DOI：10.1080/00397919408010239

  日期：1994.12

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.
• Vig,O.P. et al., Journal of the Indian Chemical Society, 1971, vol. 48, p. 993 - 999
  作者：Vig,O.P. et al.

  DOI：——

  日期：——
• Ho, Tse-Lok, Synthetic Communications, 1981, vol. 11, # 3, p. 237 - 240
  作者：Ho, Tse-Lok

  DOI：——

  日期：——