3-甲基十一烷-2-酮 | 1534-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲基十一烷-2-酮
• 英文名称: 3-methylundecan-2-one
• 英文别名: 3-methyl-2-undecanone
• CAS: 1534-28-7
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: KSIQCBVUTKCESV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-癸醇 在 三溴化磷 、 magnesium 作用下， 反应 2.0h， 生成 3-甲基十一烷-2-酮
  参考文献：
  名称：

  Midgley, Gary; Thomas, C. Barry, Journal of the Chemical Society. Perkin transactions II, 1987, p. 1103 - 1108

  摘要：

  DOI：

文献信息

• One-carbon homologation of unsymmetrical ketones through magnesium β-oxido carbenoid rearrangement and trapping the enolate intermediates with electrophiles
  作者：Shu Tanaka、Takehiro Anai、Makoto Tadokoro、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2008.05.079

  日期：2008.7

  A procedure for one-carbon homologation of unsymmetrical ketones, including one-carbon ring-expansion of 2-substituted cyclohexanones, through magnesium β-oxido carbenoid rearrangement as the key reaction is described. Addition of the α-sulfinyl carbanion of 1-chloroethyl p-tolyl sulfoxide to an unsymmetrical ketone gave two diastereomers as adducts in good yields. The adducts were treated with a base

  描述了一种通过不对称酮的一碳同系化（包括2-取代的环己酮的一碳环扩展）通过镁β-氧化类胡萝卜素重排作为关键反应的方法。1-氯乙基p的α-亚磺酰基碳负离子的加成甲苯磺酸亚砜制得不对称酮后，以高收率得到了两种非对映异构体作为加合物。将加合物用碱处理以得到醇盐，将其用格氏试剂处理以得到β-氧化类胡萝卜素镁。然后进行β-氧化类胡萝卜素重排，以提供在α-位具有甲基的一碳同系酮。在重排中观察到显着的特异性或选择性。发现该反应的烯醇镁中间体能够被数种亲电试剂捕获，从而得到一碳同系的α，α-二取代的酮。还讨论了特异性和选择性的起源。
• Nucleophilic addition to 2-imidazolines. A ketone synthesis via tetrahydrofolate coenzyme models
  作者：Michael W. Anderson、Raymond C. F. Jones、John Saunders

  DOI：10.1039/c39820000282

  日期：——

  2-Alkyl-1-benzyl-3-methyl-2-imidazolinium salts with Grignard reagents give addition products that are hydrolysed to ketone; 2-imidazolines and 2-imidazolinium salts with hydride reagents afford N-alkylated 1,2-diaminoethanes.

  用格氏试剂制得的2-烷基-1-苄基-3-甲基-2-咪唑啉鎓盐可将加成产物水解为酮；用氢化试剂将2-咪唑啉和2-咪唑啉盐得到N-烷基化的1，2-二氨基乙烷。
• Organomanganese (II) reagents XVI1: copper-catalyzed 1,4-addition of organomanganese chlorides to conjugated enones
  作者：Gérard Cahiez、Mouad Alami

  DOI：10.1016/s0040-4039(00)99434-6

  日期：1989.1

  Copper-catalyzed conjugate addition of organomanganese chlorides to conjugated enones in THF, at 0°C, leads to the 1,4 addition products in high yields. The scope of the reaction is very large and the results are generally better than those obtained from organomagnesium compounds in the presence of a copper salt as well as from organocopper or cuprate reagents. Furthermore organomanganese chlorides are indisputably

  在0℃下，铜催化的有机锰氯化物在THF中的共轭烯酮的共轭加成反应，可高产率地产生1,4加成产物。该反应的范围非常大，其结果通常比在铜盐以及有机铜或铜酸盐试剂存在下从有机镁化合物获得的结果更好。此外，有机锰氯化物无疑比后者更便宜，更稳定。
• Highly dispersed potassium on alumina as a metalating agent. Alkylation of enolizable compounds
  作者：Diego Savoia、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1016/s0022-328x(00)80496-9

  日期：1981.1

  Highly dispersed potassium on alumina (K/Al2O3) acts as a metalating agent towards enolizable compounds and the intermediate organopotassium derivatives can be alkylated with primary alkyl bromides. The reaction conditions are dependent on the substrate. In particular, tetrahydrofuran is the solvent of choice for the metalation of nitriles and aldehydeN,N-dimethylhydrazones at −60°C and of N-cyclohexyl

  氧化铝上高度分散的钾（K / Al 2 O 3）作为可烯醇化化合物的金属化剂，中间有机钾衍生物可以用伯烷基溴化物烷基化。反应条件取决于底物。特别地，四氢呋喃是在-60℃下腈和醛N，N-二甲基hydr和N-环己基酮亚胺在室温下金属化的选择的溶剂，而己烷必须用于酮。
• Volatiles from the Psychrotolerant Bacterium <i>Chryseobacterium polytrichastri</i>
  作者：Lukas Lauterbach、Jeroen S. Dickschat

  DOI：10.1002/cbic.202000503

  日期：2020.12.11

  Over 70 volatile organic compounds have been identified in a headspace extract from C. polytrichastri. The extract was particularly rich in nitrogen‐containing natural products, many of which were structurally derived from 2‐phenylethylamine. Several compounds are new natural products, their suggested structures are based on the observed mass spectral fragmentation, confirmed by synthesis of reference

  在C. polytrichastri的顶空提取物中已鉴定出70 多种挥发性有机化合物。该提取物富含含氮天然产物，其中许多在结构上源自 2-苯乙胺。几种化合物是新的天然产物，它们的建议结构基于观察到的质谱碎片，并通过参考物质的合成得到证实。