(R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one | 1426140-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one
• 英文别名: (2R)-2-(2-hydroxypent-4-en-1-yl)-6-((E)-styryl)-2,3-dihydro-4Hpyran-4-one；(2R)-2-[(2S)-2-hydroxypent-4-enyl]-6-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one
• CAS: 1426140-07-9
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: TVOSRMOVQJNSTI-VSNRRYGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-6-{[(R)-4-oxo-6-[(E)-styryl]-3,4-dihydro-2H-pyran-2-yl]methyl}-5,6-dihydro-2H-pyran-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
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 copper(l) iodide 、 2-iodoxybenzoic acid 、 三氟甲磺酸二丁硼 、 [Me₂NH₂]^-[RuCl(S-BINAP)]₂(μ-Cl)3⁺ 、 氢气 、 氧气 、 对甲苯磺酸 、 三乙胺 、 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 、 丙酮 为溶剂， -78.0~110.0 ℃ 、12.8 MPa 条件下， 反应 18.09h， 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

文献信息

• Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones
  作者：Deepak Saini、Praveen Kumar、Rodney A. Fernandes

  DOI：10.1039/d1nj03990c

  日期：——

  A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material, L-aspartic acid. Next, the allylation reaction was strategically utilized

  使用无金属催化 δ-羟基炔酮重排实现了两种非对映异构 obolactones 和 7',8'-二氢obolactones 的简洁立体选择性全合成，这可以提供所需的二氢-γ-吡喃酮部分。所需的第一个立体中心通过手性池材料L-天冬氨酸安装。接下来，烯丙基化反应被策略性地用于为预期的闭环复分解提供必要的烯烃键，允许在天然产物中安装剩余的二氢-α-吡喃酮部分。它还能够靶向两种二氢-α-吡喃酮非对映异构体。因此，首次立体选择性全合成 (+)-7',8'-二氢花生内酯完成，确定其结构和绝对构型。
• 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.