1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]propan-2-one | 1426140-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]propan-2-one
• 英文别名: 1-[(4R,6S)-2,2-dimethyl-6-prop-2-enyl-1,3-dioxan-4-yl]propan-2-one
• CAS: 1426140-03-5
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: GRFVUGMTXVEGGR-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]propan-2-one 在 2-iodoxybenzoic acid 、 三氟甲磺酸二丁硼 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 9.67h， 生成 (R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Obolactone Based on a Symmetry-Breaking Wacker Monooxidation of a Diene

  摘要：

  A concise synthesis of the dihydro-alpha-pyrone/dihydro-gamma-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (>= 97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-gamma-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (-> 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-alpha-pyrone moiety of the target in the terminating step.

  DOI：

  10.1021/ol400232m
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 copper(l) iodide 、 [Me₂NH₂]^-[RuCl(S-BINAP)]₂(μ-Cl)3⁺ 、 氢气 、 氧气 、 对甲苯磺酸 、 copper(l) chloride 、 potassium hydroxide 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~110.0 ℃ 、12.8 MPa 条件下， 反应 8.42h， 生成 1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]propan-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Obolactone Based on a Symmetry-Breaking Wacker Monooxidation of a Diene

  摘要：

  A concise synthesis of the dihydro-alpha-pyrone/dihydro-gamma-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (>= 97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-gamma-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (-> 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-alpha-pyrone moiety of the target in the terminating step.

  DOI：

  10.1021/ol400232m

文献信息

• Enantioselective Synthesis of (+)-Obolactone Based on a Symmetry-Breaking Wacker Monooxidation of a Diene
  作者：Patrick Walleser、Reinhard Brückner

  DOI：10.1021/ol400232m

  日期：2013.3.15

  A concise synthesis of the dihydro-alpha-pyrone/dihydro-gamma-pyrone natural product (+)-obolactone (13) is disclosed. The dienediol acetonide 23 (>= 97% ee) was obtained from 1,5-dichloropentane-2,4-dione in four steps. A Wacker monooxidation of 23 furnished the monoketone 24 in 64% yield. The OH group of the ensuing dihydro-gamma-pyrone 31 was esterified under Mitsunobu conditions with cinnamic acid (-> 80% inversion and 20% retention of configuration). A ring-closing metathesis formed the dihydro-alpha-pyrone moiety of the target in the terminating step.