(5R)-3-methylbut-2-enyl 2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-3-oxo-5-(tri-isopropylsilyloxy)hexanoate | 1334485-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (5R)-3-methylbut-2-enyl 2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-3-oxo-5-(tri-isopropylsilyloxy)hexanoate
• 英文别名: 3-methylbut-2-enyl (5R)-2-[2-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)acetyl]-3-oxo-5-tri(propan-2-yl)silyloxyhexanoate
• CAS: 1334485-06-1
• 化学式: C₂₈H₄₆O₈Si
• 分子量: 538.754
• InChiKey: RZFOASZJZZGPLQ-OSMGYRLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5R)-3-methylbut-2-enyl 2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-3-oxo-5-(tri-isopropylsilyloxy)hexanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40%的产率得到(R)-3-methylbut-2-enyl 7-hydroxy-2,2-dimethyl-4-oxo-5-(2-(tri-isopropylsilyloxy)propyl)-4H-benzo[d][1,3]dioxine-6-carboxylate
  参考文献：
  名称：

  Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

  摘要：

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

  DOI：

  10.1021/ol202320m
• 作为产物：
  描述：

  3-(3-methyl-2-buten-1-yl)malonate 在 吡啶 、 氯化亚砜 、 magnesium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 (5R)-3-methylbut-2-enyl 2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-3-oxo-5-(tri-isopropylsilyloxy)hexanoate
  参考文献：
  名称：

  Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

  摘要：

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

  DOI：

  10.1021/ol202320m

文献信息

• Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences
  作者：Jens Cordes、Frederick Calo、Katie Anderson、Toni Pfaffeneder、Sylvain Laclef、Andrew J. P. White、Anthony G. M. Barrett

  DOI：10.1021/jo202354j

  日期：2012.1.6

  A five-step synthesis of the natural product angelicoin A using a late stage highly regioselective palladium(0)-catalyzed decarboxylative prenyl migration and aromatization sequence as the key step is reported. The method was extended with geranyl migration in eight-step total syntheses of hericenone J and hericenol A from geraniol.
• Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence
  作者：Katie Anderson、Frederick Calo、Toni Pfaffeneder、Andrew J. P. White、Anthony G. M. Barrett

  DOI：10.1021/ol202320m

  日期：2011.11.4

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.