(4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol | 439808-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol
• 英文别名: (1R,2E,4Z)-5-bromo-1-[(2S)-2-methyloxiran-2-yl]penta-2,4-dien-1-ol
• CAS: 439808-10-3
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: CKTRPMBLYWPBMG-PZNXXSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 (2E,4Z,6E)-(R)-8-((2S,3S)-2-Amino-3-phenyl-butyryloxy)-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Asymmetric total synthesis of AK-toxins

  摘要：

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00117-5
• 作为产物：
  描述：

  (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal 在 palladium diacetate 四丁基氟化铵 、 三正丁基氢锡 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 3.5h， 生成 (4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol
  参考文献：
  名称：

  Asymmetric total synthesis of AK-toxins

  摘要：

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00117-5

文献信息

• Asymmetric total synthesis of AK-toxins
  作者：Ippei Uemura、Hisashi Miyagawa、Tamio Ueno

  DOI：10.1016/s0040-4020(02)00117-5

  日期：2002.3

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.