(6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)acetaldehyde | 872832-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)acetaldehyde
• CAS: 872832-13-8
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: CAHWYVKGDGPEBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)acetaldehyde 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 3-(6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)-4-((R)-2-(methoxymethyl)pyrrolidin-1-ylimino)butyric acid methyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  (benzyl)(4-methoxybenzyl)[6-(2-methoxyvinyl)benzo[1,3]dioxol-5-ylmethyl]amine 在 高氯酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以93%的产率得到(6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)acetaldehyde
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093