(S)-3-Methyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one | 233671-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-3-Methyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one
• 英文别名: (7aS)-3-methyl-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one
• CAS: 233671-69-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: WBBCNLFCIBFEEO-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2R,1'S,2'S)-2-(1',2'-dihydroxycyclohexyl)-N,N-diisopropylpropanamide 在 吡啶 、 氯化亚砜 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.75h， 生成 (S)-3-Methyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one
  参考文献：
  名称：

  Diastereoselective Osmylation and Hydroboration of β,γ-Unsaturated N,N-Diisopropylamides and Acid-Catalyzed Conversion to δ-Lactones

  摘要：

  The title reactions of beta,gamma-unsaturated N,N-diisopropylamides occur with useful diastereofacial selectivity. The major diol isomer from osmylation of alkenes 1, 10, 11, and 12 in the presence of TMEDA at -78 degrees C corresponds to the facial preference shown in transition state model 41 (R-z = H), while the opposite preference for 42 is observed with the Z-alkene 13. (Table 1). Hydroboration with g-BBN does not show this inversion of diastereofacial selectivity for the Z-alkene. All of the results in Table 2 correspond to the usual preference for a transition state such as 45. Acid-catalyzed lactonization of the alcohols obtained in Tables 1 and 2 can be carried out with overall retention of configuration to afford delta-lactones. Butenolide 5 was prepared with 90% se from alcohol 2a via osmylation followed by acid-catalyzed lactonization to 3 and elimination using SOCl2/pyridine.

  DOI：

  10.1021/jo990119u

文献信息

• Diastereoselective Osmylation and Hydroboration of β,γ-Unsaturated <i>N,N</i>-Diisopropylamides and Acid-Catalyzed Conversion to δ-Lactones
  作者：E. Vedejs、A. W. Kruger

  DOI：10.1021/jo990119u

  日期：1999.6.1

  The title reactions of beta,gamma-unsaturated N,N-diisopropylamides occur with useful diastereofacial selectivity. The major diol isomer from osmylation of alkenes 1, 10, 11, and 12 in the presence of TMEDA at -78 degrees C corresponds to the facial preference shown in transition state model 41 (R-z = H), while the opposite preference for 42 is observed with the Z-alkene 13. (Table 1). Hydroboration with g-BBN does not show this inversion of diastereofacial selectivity for the Z-alkene. All of the results in Table 2 correspond to the usual preference for a transition state such as 45. Acid-catalyzed lactonization of the alcohols obtained in Tables 1 and 2 can be carried out with overall retention of configuration to afford delta-lactones. Butenolide 5 was prepared with 90% se from alcohol 2a via osmylation followed by acid-catalyzed lactonization to 3 and elimination using SOCl2/pyridine.