(3AR,6AS)-二氢-6-甲氧基-2,2-二甲基呋喃[3,4-D][1,3]二恶茂烷-4(3AH)-酮 | 951377-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3AR,6AS)-二氢-6-甲氧基-2,2-二甲基呋喃[3,4-D][1,3]二恶茂烷-4(3AH)-酮
• 英文名称: (3aR,6aS)-6-Methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
• 英文别名: (3aR,6aS)-6-methoxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 951377-84-7
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: BXFYHFZSSWKNFZ-GXFGBBIGSA-N

物化性质

• 沸点：
  286.2±40.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3AR,6AS)-二氢-6-甲氧基-2,2-二甲基呋喃[3,4-D][1,3]二恶茂烷-4(3AH)-酮 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (-)-(3Ar,6ar)-四氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮
  参考文献：
  名称：

  Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues

  摘要：

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

  DOI：

  10.1021/jo071146k
• 作为产物：
  描述：

  O-methyl 2,3-O-isopropylidene-D-lyxofuranoside 在 pyridinium chlorochromate 作用下， 以 苯 为溶剂， 生成 (3AR,6AS)-二氢-6-甲氧基-2,2-二甲基呋喃[3,4-D][1,3]二恶茂烷-4(3AH)-酮
  参考文献：
  名称：

  碳环核苷和前列腺素合成子的高效对映选择性合成

  摘要：

  描述了两个羟基化的环戊烯酮2和10的简单有效的对映选择性合成，它们是直接从容易获得的糖中合成各种碳环核苷和前列腺素的有用中间体。

  DOI：

  10.1016/0040-4039(90)80002-4

文献信息

• ALI, SYED MASHHOOD;RAMESH, KAKARLA;BORCHARDT, RONALD T., TETRAHEDRON LETT., 31,(1990) N1, C. 1509-1512
  作者：ALI, SYED MASHHOOD、RAMESH, KAKARLA、BORCHARDT, RONALD T.

  DOI：——

  日期：——
• Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues
  作者：Amos B. Smith、Jeffrey B. Sperry、Qiang Han

  DOI：10.1021/jo071146k

  日期：2007.8.31

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.
• Efficient enantioselective syntheses of carbocyclic nucleoside and prostaglandin synthons
  作者：Syed Mashhood Ali、Kakarla Ramesh、Ronald T. Borchardt

  DOI：10.1016/0040-4039(90)80002-4

  日期：1990.1

  Simple and efficient enantioselective syntheses of two hydroxylated cyclopentenones, 2 and 10, which are useful intermediates for the synthesis of various carbocyclic nucleosides and prostaglandins, directly from readily available sugars are described.

  描述了两个羟基化的环戊烯酮2和10的简单有效的对映选择性合成，它们是直接从容易获得的糖中合成各种碳环核苷和前列腺素的有用中间体。