2-methyl-6-methylenecyclohexanone | 42858-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-6-methylenecyclohexanone
• 英文别名: 6-Methyl-2-methylenecyclohexanone；2-methyl-6-methylene-cyclohexanone；2-Methyl-6-methylen-cyclohexanon；2-Methylen-6-methylcyclohexanon；2,6-Dimethylcyclohex-2-enon；2-Methyl-6-methylidenecyclohexan-1-one
• CAS: 42858-50-4
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: PJXABFXUKFJZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-methyl-6-methylenecyclohexanone 、 2,4,6-三甲基苯甲腈N-氧化物 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到7-Methyl-3-(2,4,6-trimethyl-phenyl)-1-oxa-2-aza-spiro[4.5]dec-2-en-6-one
  参考文献：
  名称：

  腈与 α-亚甲基环酮的 1,3-偶极环加成反应合成新型螺异恶唑啉

  摘要：

  在苯甲腈与不同的 α-亚甲基环酮的高度区域选择性环加成反应中，以良好的收率制备了新型螺异恶唑啉。

  DOI：

  10.1080/00397919908086046
• 作为产物：
  描述：

  6-methyl-1-trimethylsiloxycyclohex-1-ene 在 potassium hydrogensulfate 、 二碘甲烷 、 铜 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-6-methylenecyclohexanone
  参考文献：
  名称：

  Novel synthesis of .alpha.-methylene carbonyl compounds

  摘要：

  DOI：

  10.1021/ja00498a031

文献信息

• A simple, effective, new, palladium-catalyzed conversion of enol silanes to enones and enals
  作者：Richard C. Larock、Timothy R. Hightower、George A. Kraus、Pat Hahn、Deye Zheng

  DOI：10.1016/0040-4039(95)00306-w

  日期：1995.4

  Enol silanes derived from aldehydes and ketones are readily converted to the corresponding α,β-unsaturated carbonyl compounds by 10% Pd(OAc)2 in the presence of one atmosphere of oxygen in DMSO as the solvent.

  在一种氧气在DMSO中作为溶剂存在下，由醛和酮衍生的烯醇硅烷很容易通过10％Pd（OAc）2转化为相应的α，β-不饱和羰基化合物。
• Synthesis of α,β-unsaturated carbonyl compounds via a visible-light-promoted organocatalytic aerobic oxidation
  作者：Junlin Zhang、Leming Wang、Qi Liu、Zhen Yang、Yong Huang

  DOI：10.1039/c3cc46778c

  日期：——

  α,β-Unsaturated ketones and aldehydes have been synthesized from their corresponding silyl enol ethers in a straightforward protocol involving a visible-light promoted organocatalytic, aerobic oxidation reaction. A cheap organic dye was used catalytically in these reactions as the photosensitizer.

  α,β-不饱和酮和醛已通过其相应的硅基烯醇醚在一种简便的协议中合成，该协议涉及可见光促进的有机催化、需氧氧化反应。在这些反应中，使用了一种廉价的有机染料作为光敏剂进行催化。
• Thiophosphates and Selenophosphates in Organic Synthesis. A New Approach to Exocyclic Olefins and Bicyclic Enones
  作者：Aleksandra Skowronska、Ewa Krawczyk、Marek Koprowski、Piotr Dybowski

  DOI：10.1080/10426509608046285

  日期：1996.2.1
• .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes
  作者：Hiroyuki Nakahira、Ilhyong Ryu、Masanobu Ikebe、Yoshiaki Oku、Akiya Ogawa、Nobuaki Kambe、Noboru Sonoda、Shinji Murai

  DOI：10.1021/jo00027a008

  日期：1992.1

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.
• Larock Richard C., Hightower Timothy R., Kraus George A., Hahn Pat, Zheng+, Tetrahedron Lett., 36 (1995) N 14, S 2423-2426
  作者：Larock Richard C., Hightower Timothy R., Kraus George A., Hahn Pat, Zheng+

  DOI：——

  日期：——