(4S,5R)-5-allyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amide | 862591-93-3

• 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: (4S,5R)-5-allyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amide
• 英文别名: (4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-N-but-3-enyl-2,2-dimethyl-5-prop-2-enyl-1,3-dioxolane-4-carboxamide
• CAS: 862591-93-3
• 化学式: C₂₁H₂₆BrNO₅
• 分子量: 452.345
• InChiKey: OWOCUCPIHVTFQK-APWZRJJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-allyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium diacetate 、 potassium osmate(VI) 、 samarium diiodide 、 草酰氯 、 Dowex-50 、 1,3-双(二苯基膦)丙烷 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 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 39.75h， 生成 (1R,14S,15R)-14,15-dihydroxy-5,7-dioxa-12-aza-tetracyclo[10.5.2.0^2,10.0^4,8]nonadeca-2,4(8),9-triene-13,17-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：

  6-溴-3,4-亚甲基二氧苯甲醛 在 sodium tetrahydroborate 、 4 A molecular sieve 、 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4S,5R)-5-allyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (6-bromobenzo[1,3]dioxol-5-ylmethyl)(but-3-enyl)amide
  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

• 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