6-(toluene-4-sulfonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9(S)-carbonitrile | 872831-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(toluene-4-sulfonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9(S)-carbonitrile
• 英文别名: (9S)-6-(4-methylphenyl)sulfonyl-5,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h][2]benzazepine-9-carbonitrile
• CAS: 872831-86-2
• 化学式: C₁₉H₁₈N₂O₄S
• 分子量: 370.429
• InChiKey: DTZQHSWBDMZGAG-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(toluene-4-sulfonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9(S)-carbonitrile 在 萘 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 28.0h， 生成 6-(2,2,5-trimethyl[1,3]dioxolane-4-carbonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9-carbonitrile
  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：

  N-甲苯磺酰基氮杂环丙烷 在 正丁基锂 、 magnesium monoperoxyphthalate hexahydrate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 14.0h， 生成 6-(toluene-4-sulfonyl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene-9(S)-carbonitrile
  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