(R)-6-Benzyl-9-[1,3]dithian-2-yl-5,6,8,9-tetrahydro-1,3-dioxa-6-aza-cyclohepta[f]inden-7-one | 872832-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (R)-6-Benzyl-9-[1,3]dithian-2-yl-5,6,8,9-tetrahydro-1,3-dioxa-6-aza-cyclohepta[f]inden-7-one
• CAS: 872832-23-0
• 化学式: C₂₂H₂₃NO₃S₂
• 分子量: 413.562
• InChiKey: JENZDZJOLUETKM-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-6-Benzyl-9-[1,3]dithian-2-yl-5,6,8,9-tetrahydro-1,3-dioxa-6-aza-cyclohepta[f]inden-7-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以92%的产率得到6-benzyl-9(R)-([1,3]dithian-2-yl)-6,7,8,9-tetrahydro-5H-1,3-dioxa-6-aza-cyclohepta[f]indene
  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：

  (R)-3-Benzo[1,3]dioxol-5-yl-3-[1,3]dithian-2-yl-propionic acid methyl ester 在 三甲基铝 、 三氟乙酸 作用下， 以 正庚烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 30.5h， 生成 (R)-6-Benzyl-9-[1,3]dithian-2-yl-5,6,8,9-tetrahydro-1,3-dioxa-6-aza-cyclohepta[f]inden-7-one
  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