3-Methylspiro<4.5>-2-decen-1-one | 85923-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methylspiro<4.5>-2-decen-1-one
• 英文别名: 3-Methylspiro[4.5]dec-2-en-1-one；2-methylspiro[4.5]dec-2-en-4-one
• CAS: 85923-88-2
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: DRCKRYBQMFKUIB-UHFFFAOYSA-N

物化性质

• 沸点：
  272.8±10.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  环己甲酸甲酯 在 tris(dibenzoylmethano)iron(III) samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.25h， 生成 3-Methylspiro<4.5>-2-decen-1-one
  参考文献：
  名称：

  Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents

  摘要：

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.

  DOI：

  10.1021/jo00077a053

文献信息

• Cyclocarbonylation of 1,1,3-trisubstituted 1,3-dienes via their Tricarbonyl iron complexes. Synthesis of cyclocondensed and (or) spirocyclic (optically active) cyclopenten-2-ones
  作者：Michel Franck-Neumann、Jean-Michel Vernier

  DOI：10.1016/s0040-4039(00)60189-2

  日期：1992.11

  Tricarbonyl iron complexes of 1,1,3 and 1,1,2,3,-substituted 1,3-dienes are decomplexed under mild conditions by aluminium halides to conjugated cyclopentenones. This is illustrated for the cyclic substitution patterns A and C, leading to spirocyclic and cyclocondensed cyclopentenones. Optically active compounds are obtained in high optical purity from complexed optically active ligands, the cyclocarbonylation

  1,1,3和1,1,2,3，-取代的1,3-二烯的三羰基铁配合物在温和的条件下被卤化铝分解为共轭的环戊烯酮。对于环状取代模式A和C说明了这一点，导致了螺环和环缩合的环戊烯酮。光学活性化合物是由络合的光学活性配体以高光学纯度获得的，环羰基化反应是立体特异性的。
• Cyclocontraction - spiroannulation: a stereoselective approach to spirocycles
  作者：Barry M. Trost、Bruce R. Adams

  DOI：10.1021/ja00352a062

  日期：1983.7
• TROST, B. M.;ADAMS, B. R., J. AMER. CHEM. SOC., 1983, 105, N 14, 4849-4850
  作者：TROST, B. M.、ADAMS, B. R.

  DOI：——

  日期：——
• Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00077a053

  日期：1993.12

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.