6-methyl-cyclohex-3-enone | 32863-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methyl-cyclohex-3-enone
• 英文别名: 6-Methyl-cyclohex-3-enon；2-Methylcyclohexen-(4)-on-(1)；6-Methylcyclohex-3-en-1-on；6-Methylcyclohex-3-en-1-one
• CAS: 32863-04-0
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: YDXDEELQNUOGGX-UHFFFAOYSA-N

物化性质

• 沸点：
  165.6±9.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-methyl-cyclohex-3-enone 、 氯磷酸二乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 1-(diethoxyphosphoryloxy)-6-methyl-1,3-cyclohexadiene
  参考文献：
  名称：

  Synthesis of cyclohexadienylstannanes – Novel example of vinylic SRN1 mechanism: A theoretical and experimental study

  摘要：

  The reaction of trimethyltinsodium (1) with 1-(diethoxyphosphoryl) oxy-1,3-cyclohexadienes in liquid ammonia under irradiation affords the corresponding 1-trimethylstannylcyclohexadienes. We suggest that these reactions occur by an S(RN)1 mechanism. On the other hand, 2-(diethoxyphosphoryl)oxy-1,3-cyclohexadiene reacts very slowly towards 1 and the substitution product decomposes under the reaction conditions employed. Thus, structurally similar compounds do not behave in the same way under ET conditions. We suggest that this behavior is mainly due to differences in spin density of their radical anions, which affect their fragmentation rates. Our results are supported by computational calculations. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.04.018
• 作为产物：
  描述：

  2-甲基苯甲醚 在 氨 、 lithium 、 叔丁醇 、 水 、 草酸 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 3.0h， 生成 6-methyl-cyclohex-3-enone
  参考文献：
  名称：

  Synthesis of cyclohexadienylstannanes – Novel example of vinylic SRN1 mechanism: A theoretical and experimental study

  摘要：

  The reaction of trimethyltinsodium (1) with 1-(diethoxyphosphoryl) oxy-1,3-cyclohexadienes in liquid ammonia under irradiation affords the corresponding 1-trimethylstannylcyclohexadienes. We suggest that these reactions occur by an S(RN)1 mechanism. On the other hand, 2-(diethoxyphosphoryl)oxy-1,3-cyclohexadiene reacts very slowly towards 1 and the substitution product decomposes under the reaction conditions employed. Thus, structurally similar compounds do not behave in the same way under ET conditions. We suggest that this behavior is mainly due to differences in spin density of their radical anions, which affect their fragmentation rates. Our results are supported by computational calculations. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.04.018

文献信息

• The Stereochemistry of the SN2' Reaction. I. Preparation of Pure trans-6-Alkyl-2-cyclohexen-1-ols
  作者：Gilbert Stork、William N. White

  DOI：10.1021/ja01599a024

  日期：1956.9
• Braude et al., Journal of the Chemical Society, 1958, p. 3336,3340
  作者：Braude et al.

  DOI：——

  日期：——
• GENET J. P.; FICINI J., TETRAHEDRON LETT., 1979, NO 17, 1499-1502
  作者：GENET J. P.、 FICINI J.

  DOI：——

  日期：——
• Cyanate resin composition and copper-clad laminate
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0612783B1

  公开（公告）日：1999-05-06
• Modulation of Pathogenicity
  申请人：Ammendola Aldo

  公开号：US20070093534A1

  公开（公告）日：2007-04-26

  The present invention relates to the use of compounds of the general Formula (XIII): wherein A 7 is C═O, C═S, SO 2 , CH—OR 13 , C═NR 12 , or CH 2 —CHOR 13 ; A 8 is C(R 14 ) 2 , O, S, or NR 12 ; A 9 is C═O, C═S, SO 2 , CH—OR 13 , C═NR 12 , or CH 2 —CHOR 13 ; m is 0, or 1 q is 0, or 1 r is 0, or 1 R 12 is H, CH 3 , CH 2 —CH 3 , C 6 H 5 , OCH 3 , OCH 2 —CH 3 , OH, or SH; R 13 is H, CH 3 , or CH 2 —CH 3 ; R 14 is H, alkyl, alkoxy, OH, or SH;