(2S,3R,4S)-1-hydroxy-2,4-dimethylhexan-3-yl (E)-cinnamate | 1362849-46-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2S,3R,4S)-1-hydroxy-2,4-dimethylhexan-3-yl (E)-cinnamate
• 英文别名: [(2S,3R,4S)-1-hydroxy-2,4-dimethylhexan-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 1362849-46-4
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: JAFMOMTVMKOBPW-APXYUBFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-1-hydroxy-2,4-dimethylhexan-3-yl (E)-cinnamate 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 [(2R,3R,4S)-2,4-dimethyl-1-oxohexan-3-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Basiliskamide A

  摘要：

  Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.

  DOI：

  10.1021/ol300282e
• 作为产物：
  描述：

  [(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylhexan-3-yl] (E)-3-phenylprop-2-enoate 在 三(二甲氨基)锍二氟三甲基硅酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以79%的产率得到(2S,3R,4S)-1-hydroxy-2,4-dimethylhexan-3-yl (E)-cinnamate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Basiliskamide A

  摘要：

  Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.

  DOI：

  10.1021/ol300282e

文献信息

• Enantioselective Synthesis of (−)-Basiliskamide A
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol300282e

  日期：2012.3.16

  Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.