(6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amine | 862591-95-5

• 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-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amine
• 英文别名: N-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)but-3-en-1-amine；N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]but-3-en-1-amine
• CAS: 862591-95-5
• 化学式: C₁₂H₁₄BrNO₂
• 分子量: 284.153
• InChiKey: SKFSKKSNILWGIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium diacetate 、 potassium osmate(VI) 、 samarium diiodide 、 草酰氯 、 1,3-双(二苯基膦)丙烷 、 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 N,N-二异丙基乙胺 、 silver carbonate 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 47.5h， 生成 (1R,14S,18R)-16,16-dimethyl-5,7,15,17-tetraoxa-12-aza-pentacyclo[10.8.2.0^2,10.0^4,8.0^14,18]docosa-2,4(8),9-triene-13,20-dione
  参考文献：
  名称：

  cripowellins A和B的1-epi糖苷配基的不对称合成。

  摘要：

  DOI：

  10.1002/anie.200500556
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以11.432 g的产率得到(6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amine
  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

文献信息

• Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine
  作者：Xiaodong Yang、Lijuan Yang、Xuequan Wang、Zhiqiang Pan、Ming Zhou、Wen Chen

  DOI：10.1055/s-0030-1259288

  日期：2011.1

  (±)-oxocrinine and (±)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1 H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.

  已经开发了一种灵活的策略，可以合成 crinine 型石蒜科生物碱，(±)-oxocrinine 和 (±)-crinine。该合成路线的一个显着特征是使用分子内 Heck 反应构建四氢-1 H-苯并[c]氮杂环骨架，并形成空间拥挤的螺环己烯酮中间体和罗宾逊环。
• Asymmetric Total Synthesis of the 1-<i>e</i><i>pi</i>-Aglycon of the Cripowellins A and B
  作者：Dieter Enders、Achim Lenzen、Michael Backes、Carsten Janeck、Kelly Catlin、Marie-Isabelle Lannou、Jan Runsink、Gerhard Raabe

  DOI：10.1021/jo0518093

  日期：2005.12.1

  [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.
• Asymmetric Synthesis of the 1-epi Aglycon of the Cripowellins A and B
  作者：Dieter Enders、Achim Lenzen、Gerhard Raabe

  DOI：10.1002/anie.200500556

  日期：2005.6.13