Octanoic acid, (1S,2R)-2,3-dihydro-1-[[(4-methylphenyl)sulfonyl]amino]-1H-inden-2-yl ester | 296242-29-0

• 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: Octanoic acid, (1S,2R)-2,3-dihydro-1-[[(4-methylphenyl)sulfonyl]amino]-1H-inden-2-yl ester
• 英文别名: [(1S,2R)-1-[(4-methylphenyl)sulfonylamino]-2,3-dihydro-1H-inden-2-yl] octanoate
• CAS: 296242-29-0
• 化学式: C₂₄H₃₁NO₄S
• 分子量: 429.58
• InChiKey: HNHLWGCQIRZKOJ-VWNXMTODSA-N

物化性质

• 沸点：
  557.9±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Octanoic acid, (1S,2R)-2,3-dihydro-1-[[(4-methylphenyl)sulfonyl]amino]-1H-inden-2-yl ester 在 过氧化氢,锂盐(1:1) 、 异丙氧基三甲基硅烷 、 三氟甲磺酸三甲基硅酯 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 (2R,5S,6S)-2-tert-Butyl-5-hexyl-6-((E)-styryl)-[1,3]dioxan-4-one
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An anti-Aldol-Based Strategy

  摘要：

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.

  DOI：

  10.1021/ol000070a
• 作为产物：
  描述：

  辛酰氯 、 N-((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)-4-methylbenzenesulfonamide 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到Octanoic acid, (1S,2R)-2,3-dihydro-1-[[(4-methylphenyl)sulfonyl]amino]-1H-inden-2-yl ester
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An anti-Aldol-Based Strategy

  摘要：

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.

  DOI：

  10.1021/ol000070a

文献信息

• Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions
  作者：Arun Ghosh、Zachary Dawson

  DOI：10.1055/s-0029-1216941

  日期：2009.9

  The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described.

  描述了使用不对称羟醛反应的几种变体作为合成生物活性靶分子的关键步骤。
• Org. Lett. 2000, 2, 2405-2407
  作者：

  DOI：——

  日期：——
• Asymmetric Synthesis of (−)-Tetrahydrolipstatin:  An <i>anti</i>-Aldol-Based Strategy
  作者：Arun K. Ghosh、Steve Fidanze

  DOI：10.1021/ol000070a

  日期：2000.8.1

  [GRAPHICS]A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro aldol reaction to append the C2' C-11 side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.