(S)-6-hydroxy-3-methoxycyclohex-2-en-1-one | 443286-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-6-hydroxy-3-methoxycyclohex-2-en-1-one
• 英文别名: (6S)-6-hydroxy-3-methoxycyclohex-2-en-1-one
• CAS: 443286-53-1
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: GBNFMOZIGXQHPS-LURJTMIESA-N

物化性质

• 沸点：
  305.4±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-hydroxy-3-methoxycyclohex-2-en-1-one 在 copper(II) bis(trifluoromethanesulfonate) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (+/-)-6-acetoxy-3-methoxycyclohex-2-en-1-one
  参考文献：
  名称：

  A New and Efficient Chemoenzymatic Route to Both Enantiomers of 4-Hydroxycyclohex-2-en-1-one

  摘要：

  [GRAPHIC]A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-hydroxycyclohex-2-en-1-one in three steps starting from 3-methoxycyclohex-2-en-1-one is described. Manganese(Ill) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of a-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclohex-2-en-1-one in high enantiomeric excess.

  DOI：

  10.1021/ol025847+
• 作为产物：
  描述：

  (S)-6-acetoxy-3-methoxycyclohex-2-en-1-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 phosphate buffer 、 正己烷 、 二甲基亚砜 为溶剂， 生成 (S)-6-hydroxy-3-methoxycyclohex-2-en-1-one
  参考文献：
  名称：

  A New and Efficient Chemoenzymatic Route to Both Enantiomers of 4-Hydroxycyclohex-2-en-1-one

  摘要：

  [GRAPHIC]A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-hydroxycyclohex-2-en-1-one in three steps starting from 3-methoxycyclohex-2-en-1-one is described. Manganese(Ill) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of a-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclohex-2-en-1-one in high enantiomeric excess.

  DOI：

  10.1021/ol025847+

文献信息

• A New and Efficient Chemoenzymatic Route to Both Enantiomers of 4-Hydroxycyclohex-2-en-1-one
  作者：Ayhan S. Demir、Ozge Sesenoglu

  DOI：10.1021/ol025847+

  日期：2002.6.1

  [GRAPHIC]A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-hydroxycyclohex-2-en-1-one in three steps starting from 3-methoxycyclohex-2-en-1-one is described. Manganese(Ill) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of a-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclohex-2-en-1-one in high enantiomeric excess.