lithium enolate of 2-pentanone | 59356-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: lithium enolate of 2-pentanone
• 英文别名: 2-Pentanone lithium enolate；Lithium;pent-1-en-2-olate
• CAS: 59356-96-6
• 化学式: C₅H₉O*Li
• 分子量: 92.0669
• InChiKey: LMKHTFFOLTWDRW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.34
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lithium enolate of 2-pentanone 、 溴乙醛 反应 0.25h， 以60%的产率得到1-bromo-2-hydroxy-4-heptanone
  参考文献：
  名称：

  Direct preparation of bromoacetaldehyde

  摘要：

  DOI：

  10.1021/jo00160a040

文献信息

• Enantiocontrolled Synthesis of 2,6-Disubstituted Piperidines by Desymmetrization of <i>m</i><i>eso</i>-<i>η</i>-(3,4,5)-Dihydropyridinylmolybdenum Complexes. Application to the Total Synthesis of (−)-Dihydropinidine and (−)-Andrachcinidine
  作者：Chutian Shu、Lanny S. Liebeskind

  DOI：10.1021/ja029537y

  日期：2003.3.1

  A conceptually new approach to the enantiocontrolled synthesis of 2,6-disubstituted piperidines was achieved by desymmetrization of meso-2,6-dimethoxy-eta-(3,4,5)-dihydropyridinylmolybdenum complexes. After protection of the piperidine nitrogen as a urethane derived from (+)- or (-)-trans-2-(alpha-cumyl)cyclohexyl (TCC), a sequential, one-pot methoxide abstraction/nucleophilic addition/methoxide a

  2,6-二取代哌啶的对映控制合成的概念上新方法是通过meso-2,6-二甲氧基-eta-(3,4,5)-dihydropyridinylmolybdenum 配合物的去对称化实现的。将哌啶氮保护为衍生自 (+)- 或 (-)-trans-2-(α-枯基) 环己基 (TCC) 的氨基甲酸酯后，依次进行一锅甲醇提取/亲核加成/甲醇提取/亲核此外，2,6-二取代-eta-(3,4,5)-二氢吡啶基钼配合物的产率很高。该序列通过高度非对映选择性甲醇盐提取 (>40:1) 进行。高产量的原脱金属和 N-脱保护为各种 2,6-二取代哌啶提供了一种简单且对映控制的合成入口。
• Synthesis of 2-[1-(Alkoxycarbonyl)alkyl]-3-methylbenzothiazolines and 3-Methyl-2-(2-oxoalkyl)benzothiazolines by the Direct Alkylation of Lithium Enolates with 3-Methylbenzothiazolium Salts
  作者：Hidenori Chikashita、Naoto Takegami、Yoshiyuki Yanase、Kazuyoshi Itoh

  DOI：10.1246/bcsj.62.3389

  日期：1989.10

  enolates derived from esters and ketones could be readily alkylated with 3-methylbenzothiazolium salts to give the novel α-(benzothiazolinyl) esters and ketones, 2-[1-(alkoxycarbonyl)alkyl]3-methylbenzothiazolines and 3-methyl-2-(2-oxoalkyl)benzothiazolines in good yields, respectively.

  多种衍生自酯和酮的烯醇锂可以很容易地用 3-甲基苯并噻唑鎓盐烷基化，得到新型 α-（苯并噻唑啉基）酯和酮、2-[1-（烷氧基羰基）烷基]3-甲基苯并噻唑啉和 3-甲基- 2-(2-氧代烷基)苯并噻唑啉分别以良好的收率。
• Synthesis of 4-Hydroxy-2-cyclopentenone Derivatives by [3 + 2] Annulation of β-Heteroatom-Substituted Acryloylsilanes and Lithium Enolate of Methyl Ketones
  作者：Kei Takeda、Yasuhiro Ohtani、Emi Ando、Ken-ichi Fujimoto、Eiichi Yoshii、Toru Koizumi

  DOI：10.1246/cl.1998.1157

  日期：1998.11

  The [3 + 2] annulation using β-[2-(pyridyl)thio] and β,β-dichloro derivatives of acryloylsilane and the lithium enolate of methyl ketones successfully proceeded to afford 4-alkyl-4-hydroxy-3-(2-pyridylthio)cyclopentanone and 4-alkyl-3-chloro-4-hydroxy-2-cyclopentenone, respectively.

  丙烯酰硅烷的β-[2-(吡啶基)硫代]和β,β-二氯衍生物与甲基酮的烯醇锂成功地进行[3+2]环化，得到4-烷基-4-羟基-3-(2 -吡啶硫基）环戊酮和 4-烷基-3-氯-4-羟基-2-环戊烯酮，分别。
• Synthesis of the C1′–C11′ portion of pamamycin-607 via a stereoselective oxymercuration of a gamma—silyloxyallene and a stereospecific magnesium—methanol reduction
  作者：Robert D. Walkup、Gyoosoon Park

  DOI：10.1016/s0040-4039(00)80798-4

  日期：1988.1

  The C1′–C11′ portion of the antibiotic pamamycin-607, a novel homologue and C2-epimer of nonactic acid, was synthesized in six steps from 4,5-hexadien-1-ol via a novel -selective oxymercuration/transpalladation/methoxycarboxylation of a γ-silyloxyallene and a -selective reduction of a 2-(2-tetrahydrofuranyl)acrylate using magnesium in methanol. Spectroscopic properties of a derivative of the synthetic

  的C 1'〜C 11'的抗生素pamamycin-607，一种新颖的同系物和C的部分2 nonactic酸差向异构体，在六个步骤通过一种新颖的合成由4,5-己二烯-1-醇-选择性oxymercuration /使用甲醇中的镁，将γ-甲硅烷基氧丙烯烯进行palpalpalation /甲氧基羧化反应，并选择性地还原2-（2-四氢呋喃基）丙烯酸酯。合成℃的衍生物的光谱性质1' -C 11'部分匹配的材料从天然产物衍生的。
• The addition of metallo enolates to chiral 1-acylpyridinium salts. An asymmetric synthesis of (-)-sedamine
  作者：Daniel L. Comins、Hao Hong

  DOI：10.1021/jo00071a005

  日期：1993.9

  Synthetically useful 2-(2-oxoalkyl)-2,3-dihydro-4-pyridones are prepared in high diastereomeric excess by addition of ketone metallo enolates to chiral 1-acyl-4-methoxypyridinium salts.