3-methylene-2-methyl-2-heptanol | 50965-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylene-2-methyl-2-heptanol
• 英文别名: 2-Methyl-3-methylen-heptan-2-ol；3-butyl-2-methyl-but-3-en-2-ol；2-Methyl-3-methylideneheptan-2-ol
• CAS: 50965-92-9
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: PMQLTEPDOMWIJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  n-butylcopper 、 sodium salt of 1,1-dimethylpropynol 以 四氢呋喃 为溶剂， 生成 3-methylene-2-methyl-2-heptanol
  参考文献：
  名称：

  Addition d'alkylcuivres sur divers dérivés propargyliques

  摘要：

  DOI：

  10.1016/s0022-328x(00)86599-7

文献信息

• A Novel Palladium-Catalyzed Asymmetric Cyclocarbonylation of Allylic Alcohols to γ-Butyrolactones
  作者：Wing-Yiu Yu、Corinne Bensimon、Howard Alper

  DOI：10.1002/chem.19970030313

  日期：——

  AbstractA catalyst system based on [Pd2(dba)3]·CHCl3/(‐)‐BPPM has been found to effect asymmetric cyclocarbonylation of certain prochiral allylic alcohols to produce good yields of optically enriched γ‐butyrolactones. The reaction was performed under an atmosphere of H2 (400 psi) and CO (400 psi) at 100°C in methylene chloride for 48 hours. Asymmetric cyclocarbonylation of allylic alcohols with aliphatic substituents proceeded with moderate enantioselectivities (ee = 25–43%). However, enantiomeric excesses of up to 83% were obtained for substrates containing aromatic substituents, in which case the ee was found to be more sensitive to steric, rather than to electronic factors. Recrystallization of the lactones containing an aromatic group from a mixture of CH2Cl2/Et2O/hexanes (0.5/1.0/8.5), by slow evaporation of the solvent or at low temperature, improved the enantiopurities to >98% ee on a reproducible basis. The asymmetric center of the aromatic lactones was assigned the (S)‐configuration based on the X‐ray crystal structure analysis of enantiopure (S)‐(+)‐3,3‐dimethyl‐2‐(2′‐methylphenyl)‐γ‐butyrolactone (2k). A hydridopalladium intermediate is believed to play a key role in this reaction. Enantioselectivity is thought to be brought about by the preferential formation of 6b. The carbon skeleton of 6b fits into the chiral scaffold of (‐)‐BPPM.