6-allyl-2,6-dimethyl-2-cyclohexen-1-one | 152429-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-allyl-2,6-dimethyl-2-cyclohexen-1-one
• 英文别名: 2,6-Dimethyl-6-prop-2-enylcyclohex-2-en-1-one
• CAS: 152429-49-7
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: LFQDKTIREATCAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  6-allyl-2,6-dimethyl-2-cyclohexen-1-one 在 盐酸 、 sodium hydroxide 、 重铬酸吡啶 、 双氧水 、 4-甲基苯磺酸吡啶 、 二(3-甲基丁烷-2-基)硼烷 、 sodium hydride 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 104.17h， 生成 ethyl (Z)-5-(2-formyl-1,3-dimethyl-2-cyclohexenyl)-2-trimethylsilylmethyl-2-pentenoate
  参考文献：
  名称：

  Synthesis of a Stereoisomer of Frullanolide Utilizing the Intramolecular Cyclization ofω-Formyl-2-alkenylsilane

  摘要：

  据报道，通过 ω-甲酰基-α-三甲基甲硅烷基甲基-α,β-不饱和酯的分子内环化合成了 10-epi-frullanolide (3)。环化前体 (Z)-5-(2-甲酰基-1,3-二甲基-2-环己烯基)-2-三甲基甲硅烷基甲基-2-戊烯酸酯 (17) 由 2,6-二甲基-2-环己烯制备-1-酮通过二醛单缩醛为关键中间体。 17与四丁基氟化铵环化生成具有C(6α)-H和C(7β)-H的羟基酯，将其水解，然后进行藤泽内酯化得到3。

  DOI：

  10.1246/bcsj.66.2298
• 作为产物：
  描述：

  6-Allyl-2,6-dimethyl-cyclohexa-2,4-dienon 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0~22.0 ℃ 、30.0 kPa 条件下， 生成 6-allyl-2,6-dimethyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Stereoselective synthesis of cyclohexa-2,4-dien-1-ones and cyclohex-2-en-1-ones from phenols

  摘要：

  A convenient synthetic method for the synthesis of substituted cyclohex-2-en-1-ones by the direct alkylation of phenols has been developed. Furthermore, enantiomerically enriched 2,6-dimethyl-6-(3-methylbut-2-enyl)-cyclohexa-2,4-dienone was prepared by the deprotonation of 2,6-dimethylphenol with a sparteine-lithium complex followed by alkylation with 1-chloro-3-methylbut-2-ene. 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone was prepared from the corresponding cyclohexa-2,4-dien-1-one by selective hydrogenation of the 4,5-double bond. The method was extended to 2-methyl-naphthalen-1-ol and 1-methyl-naphthalen-2-ol resulting in 2-(R)methyl-2-(3-methylbut-2-enyl)-2H-naphthalen- 1-one and 1-(S)-methyl-1-(3-methylbut-2-enyl)-1H-naphthalen-2-one, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.017

文献信息

• TORI, MOTOO;YOSHIMURA, SHIN;KURODA, CHIAKI;ASAKAWA, YOSHINORI, CHEM. LETT.,(1990) N1, C. 2117-2120
  作者：TORI, MOTOO、YOSHIMURA, SHIN、KURODA, CHIAKI、ASAKAWA, YOSHINORI

  DOI：——

  日期：——
• Synthesis of a Stereoisomer of Frullanolide Utilizing the Intramolecular Cyclization of<i>ω</i>-Formyl-2-alkenylsilane
  作者：Chiaki Kuroda、Shigeru Shimizu、Takahiro Haishima、James Y. Satoh

  DOI：10.1246/bcsj.66.2298

  日期：1993.8

  Synthesis of 10-epi-frullanolide (3) is reported via the intramolecular cyclization of ω-formyl-α-trimethylsilylmethyl-α,β-unsaturated ester. The cyclization precursor, ethyl (Z)-5-(2-formyl-1,3-dimethyl-2-cyclohexenyl)-2-trimethylsilylmethyl-2-pentenoate (17), was prepared from 2,6-dimethyl-2-cyclohexen-1-one through the dialdehyde monoacetal as the key intermediate. Cyclization of 17 with tetrabutylammonium fluoride produced the hydroxy ester having C(6α)–H and C(7β)–H, which was hydrolyzed, then subjected to Fujisawa’s lactonization to afford 3.

  据报道，通过 ω-甲酰基-α-三甲基甲硅烷基甲基-α,β-不饱和酯的分子内环化合成了 10-epi-frullanolide (3)。环化前体 (Z)-5-(2-甲酰基-1,3-二甲基-2-环己烯基)-2-三甲基甲硅烷基甲基-2-戊烯酸酯 (17) 由 2,6-二甲基-2-环己烯制备-1-酮通过二醛单缩醛为关键中间体。 17与四丁基氟化铵环化生成具有C(6α)-H和C(7β)-H的羟基酯，将其水解，然后进行藤泽内酯化得到3。
• Stereoselective synthesis of cyclohexa-2,4-dien-1-ones and cyclohex-2-en-1-ones from phenols
  作者：Martin A. Lovchik、Andreas Goeke、Georg Fráter

  DOI：10.1016/j.tetasy.2006.06.017

  日期：2006.7

  A convenient synthetic method for the synthesis of substituted cyclohex-2-en-1-ones by the direct alkylation of phenols has been developed. Furthermore, enantiomerically enriched 2,6-dimethyl-6-(3-methylbut-2-enyl)-cyclohexa-2,4-dienone was prepared by the deprotonation of 2,6-dimethylphenol with a sparteine-lithium complex followed by alkylation with 1-chloro-3-methylbut-2-ene. 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone was prepared from the corresponding cyclohexa-2,4-dien-1-one by selective hydrogenation of the 4,5-double bond. The method was extended to 2-methyl-naphthalen-1-ol and 1-methyl-naphthalen-2-ol resulting in 2-(R)methyl-2-(3-methylbut-2-enyl)-2H-naphthalen- 1-one and 1-(S)-methyl-1-(3-methylbut-2-enyl)-1H-naphthalen-2-one, respectively. (c) 2006 Elsevier Ltd. All rights reserved.