(3R,5S,6S)-6-(3-bromoprop-1-en-2-yl)-3,5-dimethyloxan-2-one | 335060-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5S,6S)-6-(3-bromoprop-1-en-2-yl)-3,5-dimethyloxan-2-one
• CAS: 335060-55-4
• 化学式: C₁₀H₁₅BrO₂
• 分子量: 247.132
• InChiKey: HBACHRKPCFMVHL-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,5S,6S)-6-(3-bromoprop-1-en-2-yl)-3,5-dimethyloxan-2-one 在 indium 、 碳酸氢钠 、 氯化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2
• 作为产物：
  描述：

  (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium chlorite 、 N-溴代丁二酰亚胺(NBS) 、 L-(+)-酒石酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 二异丁基氢化铝 、 对甲苯磺酸 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 phosphate buffer 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 生成 (3R,5S,6S)-6-(3-bromoprop-1-en-2-yl)-3,5-dimethyloxan-2-one
  参考文献：
  名称：

  Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids

  摘要：

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02157-2

文献信息

• Highly chemoselective oxidation of 1,5-diols to δ-lactones with TEMPO/BAIB
  作者：T.Matthew Hansen、Gordon J. Florence、Priscilla Lugo-Mas、Jiehao Chen、Jason N. Abrams、Craig J. Forsyth

  DOI：10.1016/s0040-4039(02)02489-9

  日期：2003.1

  The selective oxidative conversion of a variety of highly functionalized 1degrees,2degrees-1,5-diols into the corresponding delta-lactones has been effected simply and efficiently using a reagent system comprised of catalytic 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and excess bis-acetoxyiodobenzene (BAIB). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Remarkably chemoselective indium-mediated coupling en route to the C21–C40 acyclic portion of the azaspiracids
  作者：Junliang Hao、Josep Aiguade、Craig J Forsyth

  DOI：10.1016/s0040-4039(00)02157-2

  日期：2001.1

  A densely functionalized acyclic intermediate representing the C21-C40 portion of the novel marine natural product azaspiracid was prepared via a chemoselective indium-mediated coupling between C21-C27 and C28-C40 intermediates. Although the coupling partners contained aldehyde, azide, ketone, enone, and lactone functionalities. the C21-C27 allylic species added selectively to the aldehyde of a C28-C40 intermediate under aqueous indium-mediated conditions. The C21-C27 and C35-C40 fragments were prepared in a divergent fashion from a common syn-1,3-dimethyl synthon 9. (C) 2001 Elsevier Science Ltd. All rights reserved.