3,5,5,6-tetramethyl-2-cyclohexenone | 16782-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,5,6-tetramethyl-2-cyclohexenone
• 英文别名: 2,3,3,5-Tetramethyl-cyclohexen-(5)-on-(1)；3,5,5,6-Tetramethyl-2-cyclohexen-1-on；3,5,5,6-Tetramethyl-cyclohexen-(2)-on-(1)；3,5,5,6-Tetramethyl-cyclohex-2-en-1-on；1,1,3,6-Tetramethyl-cyclohexen-(3)-on-(5)；3,5,5,6-tetramethyl-cyclohex-2-enone；3,5,5,6-Tetramethyl-cyclohex-2-enon；3,5,5,6-Tetramethylcyclohex-2-en-1-one
• CAS: 16782-80-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: SDVOAXYGGMIAIV-UHFFFAOYSA-N

物化性质

• 沸点：
  209.7±10.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3,5,5,6-tetramethyl-2-cyclohexenone 、 manganese triacetate 以 苯 为溶剂， 反应 10.0h， 以76%的产率得到(+/-)-6-acetoxy-3,5,5,6-tetramethyl-2-cyclohexen-1-one
  参考文献：
  名称：

  乙酸锰（III）氧化环状α，β-不饱和酮上的α'-取代基

  摘要：

  描述了用乙酸锰（III）选择性氧化各种2-环戊烯酮，2-环己烯酮和芳族酮衍生物上的叔α'-位置。

  DOI：

  10.1016/s0040-4020(03)01094-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 水 、 溶剂黄146 作用下， 生成 3,5,5,6-tetramethyl-2-cyclohexenone
  参考文献：
  名称：

  427.萜烯化合物。第十部分。（±）-角度的合成

  摘要：

  DOI：

  10.1039/jr9560002179

文献信息

• Favorskii rearrangement of α,β-epoxy ketones
  作者：R.W. Mouk、K.M. Patel、W. Reusch

  DOI：10.1016/0040-4020(75)80004-4

  日期：1975.1

  or (2) Favorskii rearrangement via a cyclopropanone or zwitterion intermediate. Among the factors that appear to control these reactions, it is suspected that an α′-substituent effect may operate. Such an effect has been confirmed by observing the conversion of 3,5,5,6 - tetramethyl - 2,3 - epoxycyclohexanone (1) to the ring-contracted γ-lactone 3, together with other Favorskii rearrangement products

  α，β-环氧酮与亲核碱的反应通常采取以下两个过程之一：（1）α置换，然后除水（β），或（2）通过环丙烷酮或两性离子中间体进行的Favorskii重排。在似乎控制这些反应的因素中，怀疑有α'取代作用可能起作用。通过观察3,5,5,6-四甲基-2,3-环氧环己酮（1）向环缩合的γ-内酯3以及其他Favorskii重排产物在回流处理中的转化，可以证实这种效果。甲醇氢氧化钾。在相似的反应条件下将α'-甲基取代的类固醇2转化为大致等量的4，5和4（均通过类似Favorskii的机制进行了合理化）。在每种情况下，缺少α'-Me取代基的类似环氧酮均无法产生任何Favorskii产品。
• METHODS FOR PRODUCING FUELS, GASOLINE ADDITIVES, AND LUBRICANTS USING AMINE CATALYSTS
  申请人：The Regents of the University of California

  公开号：US20170327448A1

  公开（公告）日：2017-11-16

  Provided herein are methods for producing α,β-unsaturated ketones from the condensation of methyl ketones in the presence of an amine catalyst. Such amine catalysts may be supported, for example, on a silica-alumina support. Such amine catalysts may be used in the presence of an additional acid. The α,β-unsaturated ketones may be produced by dimerization and/or timerization of the methyl ketones. Such α,β-unsaturated ketones may be suitable for use in producing fuels, gasoline additives, and/or lubricants, or precursors thereof. The methyl ketones may be obtained from renewable sources, such as by the fermentation of biomass.

  本文提供了一种制备α，β-不饱和酮的方法，该方法是通过在胺催化剂存在下对甲基酮进行缩合反应实现的。这样的胺催化剂可以被负载在二氧化硅-氧化铝载体上。这样的胺催化剂可以在存在额外酸的情况下使用。α，β-不饱和酮可以通过甲基酮的二聚化和/或三聚化产生。这样的α，β-不饱和酮可适用于生产燃料、汽油添加剂和/或润滑剂，或其前体。甲基酮可以从可再生来源获得，例如通过生物质发酵。
• Chapurlat,R. et al., Bulletin de la Societe Chimique de France, 1967, p. 2446 - 2450
  作者：Chapurlat,R. et al.

  DOI：——

  日期：——
• Manganese(III) acetate based selective oxidation of the tertiary α′-position on various cyclic α,β-unsaturated ketones
  作者：Cihangir Tanyeli、Bengü Sezen、Çigdem İyigün、Olcay Elmalı

  DOI：10.1016/s0040-4039(01)01262-x

  日期：2001.9

  We describe the preliminary results of manganese(III) acetate based selective oxidation of various alpha ' -methyl 2-cyclohexenone and 2-cyclopentenone derivatives to afford the corresponding alpha ' -acetoxy-alpha ' -methyl substituted oxidation products in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The first enzymatic resolution of quaternary α′-acetoxy α,β-unsaturated cyclohexenones and cyclopentenones
  作者：Cihangir Tanyeli、Fazilet Devrim Özdemirhan、Çiğdem İyigün

  DOI：10.1016/j.tetasy.2005.11.016

  日期：2005.12

  The enantio selective resolution of various quaternary alpha'-acetoxy alpha,beta-unsaturated cyclohexenones and cyclopentenones was performed with the commercially available enzyme CCL in pH = 8.0 phosphate buffer. Various parameters that would affect the enantioselectivities were tested and the best enzymatic resolution conditions were found to afford the enantiomerically enriched quaternary acetoxylated substrates with high ee varying between 36% and 99%. (c) 2005 Elsevier Ltd. All rights reserved.