(4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,2-dimethyl-5-(2-oxopropyl)-N-(2-phenylmethoxyethyl)-1,3-dioxolane-4-carboxamide | 872831-88-4

• 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)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,2-dimethyl-5-(2-oxopropyl)-N-(2-phenylmethoxyethyl)-1,3-dioxolane-4-carboxamide
• CAS: 872831-88-4
• 化学式: C₂₆H₃₀BrNO₇
• 分子量: 548.431
• InChiKey: UFOGCRMYCNYIOW-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,2-dimethyl-5-(2-oxopropyl)-N-(2-phenylmethoxyethyl)-1,3-dioxolane-4-carboxamide 、 叔丁基二甲硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到(4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-5-[2-[tert-butyl(dimethyl)silyl]oxyprop-2-enyl]-2,2-dimethyl-N-(2-phenylmethoxyethyl)-1,3-dioxolane-4-carboxamide
  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：

  2-苄基-1-乙胺 在 sodium tetrahydroborate 、 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 (4S,5R)-N-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,2-dimethyl-5-(2-oxopropyl)-N-(2-phenylmethoxyethyl)-1,3-dioxolane-4-carboxamide
  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.