6-acetoxy-3-methoxy-2-methyl-2-cyclohexen-1-one | 132783-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-acetoxy-3-methoxy-2-methyl-2-cyclohexen-1-one
• 英文别名: Xvbhlqnxvzwwtb-uhfffaoysa-；(4-methoxy-3-methyl-2-oxocyclohex-3-en-1-yl) acetate
• CAS: 132783-35-8
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: XVBHLQNXVZWWTB-UHFFFAOYSA-N

物化性质

• 沸点：
  308.4±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-acetoxy-3-methoxy-2-methyl-2-cyclohexen-1-one 在 lithium aluminium tetrahydride 、 pig liver esterase 、 potassium phosphate buffer 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (S)-4-hydroxy-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.006
• 作为产物：
  描述：

  3-methoxy-2-methylcyclohex-2-en-1-one 、 manganese triacetate 以 苯 为溶剂， 生成 6-acetoxy-3-methoxy-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.006

文献信息

• The Oxidation of β-Alkoxycyclopentenones and β-Alkoxycyclohexenones to α′-Acyloxy Derivatives Using Manganese(III) Acetate in Combination with Carboxylic Acids
  作者：Ayhan S. Demir、Tugmac Sayrac、David S. Watt

  DOI：10.1055/s-1990-27108

  日期：——

  The α′-oxidation of cyclic derivatives of β-alkoxy-α,β-unsaturated ketones using manganese(III) acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-3-alkoxy-2-cyclopentenones and 6-acyloxy-3-alkoxy-2-cyclohexenones.

  在各种羧酸存在下，使用乙酸锰（III）对δ-烷氧基-δ,δ-不饱和酮的环状衍生物进行δ′-氧化，可方便地合成 5-乙酰氧基-3-烷氧基-2-环戊烯酮和 6-乙酰氧基-3-烷氧基-2-环己烯酮。
• DEMIR, AYHAN S.;SAYRAC, TUGMAC;WATT, DAVID S., SYNTHESIS (BRD),(1990) N2, C. 1119-1121
  作者：DEMIR, AYHAN S.、SAYRAC, TUGMAC、WATT, DAVID S.

  DOI：——

  日期：——
• A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones
  作者：Ayhan S. Demir、Hamide Fındık、Elif Köse

  DOI：10.1016/j.tetasy.2003.12.006

  日期：2004.3

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

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