2-(1,2-Dihydroxy-cyclohexyl)-propionic acid ethyl ester | 143836-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,2-Dihydroxy-cyclohexyl)-propionic acid ethyl ester
• CAS: 143836-99-1
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: IFQRSADDCSUKIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(1,2-Dihydroxy-cyclohexyl)-propionic acid ethyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以84%的产率得到2,4,5,6,7,7a-Hexahydro-3-methyl-1-benzofuran-2-on
  参考文献：
  名称：

  An efficient entry into butenolides: Synthesis of (±) mintlactone

  摘要：

  Osmylation of beta,gamma-unsaturated esters and acid catalysed cyclisation of the resultant diols generate butenolides in high yields.

  DOI：

  10.1016/s0040-4039(00)61325-4
• 作为产物：
  描述：

  2-cyclohex-1-enyl-propionic acid ethyl ester 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以87%的产率得到2-(1,2-Dihydroxy-cyclohexyl)-propionic acid ethyl ester
  参考文献：
  名称：

  An efficient entry into butenolides: Synthesis of (±) mintlactone

  摘要：

  Osmylation of beta,gamma-unsaturated esters and acid catalysed cyclisation of the resultant diols generate butenolides in high yields.

  DOI：

  10.1016/s0040-4039(00)61325-4

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.