(3aS,7aR,4'R)-5-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-7a-hydroxymethyl-4-methyl-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one | 645394-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (3aS,7aR,4'R)-5-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-7a-hydroxymethyl-4-methyl-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one
• 英文别名: (3aR,7aS)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7a-(hydroxymethyl)-4-methyl-3,3a,6,7-tetrahydro-2-benzofuran-1-one
• CAS: 645394-03-2
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: MHBNOFGTWJIGQT-TYNCELHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,7aR,4'R)-5-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-7a-hydroxymethyl-4-methyl-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(3aS,7aR)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-7-methyl-3-oxo-1,4,5,7a-tetrahydro-isobenzofuran-3a-carbaldehyde
  参考文献：
  名称：

  Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition

  摘要：

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.

  DOI：

  10.1021/ol035939e
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylidene-N-methoxy-N-methylpropanamide 在 sodium tetrahydroborate 、 正丁基锂 、 pH 7 buffer 、 溶剂黄146 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 60.17h， 生成 (3aS,7aR,4'R)-5-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-7a-hydroxymethyl-4-methyl-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition

  摘要：

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.

  DOI：

  10.1021/ol035939e

文献信息

• Studies on the Synthesis of Gymnodimine. Construction of the Spiroimine Portion via Diels−Alder Cycloaddition
  作者：James D. White、Guoqiang Wang、Laura Quaranta

  DOI：10.1021/ol035939e

  日期：2003.12.1

  [GRAPHICS]An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled.