(4SR,5RS)-4,5-epoxyoctanoic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4SR,5RS)-4,5-epoxyoctanoic acid tert-butyl ester
• 英文别名: tert-butyl 3-[(2S,3R)-3-propyloxiran-2-yl]propanoate
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: DAZGYSCTURKWQJ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4SR,5RS)-4,5-epoxyoctanoic acid tert-butyl ester 在 ((1S,2R,5S)-2-i-Pr-5-Me-cyclohex-1-yl)Cp)2TiCl₂ 锰 、 1,4-环己二烯 、 2,4,6-collidine hydrochloride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 (R)-5-正丁基二氢呋喃-2-酮
  参考文献：
  名称：

  Titanocene-Catalyzed Regiodivergent Epoxide Openings

  摘要：

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.

  DOI：

  10.1021/ja0686211
• 作为产物：
  描述：

  顺-2-己烯-1-醇 在 三乙胺 、 间氯过氧苯甲酸 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (4SR,5RS)-4,5-epoxyoctanoic acid tert-butyl ester
  参考文献：
  名称：

  Titanocene-Catalyzed Regiodivergent Epoxide Openings

  摘要：

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.

  DOI：

  10.1021/ja0686211

文献信息

• Regiodivergent epoxide opening (REO) via electron transfer: control elements
  作者：Andreas Gansäuer、Lei Shi、Florian Keller、Peter Karbaum、Chun-An Fan

  DOI：10.1016/j.tetasy.2010.03.052

  日期：2010.6

  The first regiodivergent opening of unbiased epoxides (REO) providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides. The dependence of the selectivity of ring opening on the epoxide's substitution pattern was studied. (C) 2010 Elsevier Ltd. All rights reserved.
• Titanocene-Catalyzed Regiodivergent Epoxide Openings
  作者：Andreas Gansäuer、Chun-An Fan、Florian Keller、Jutta Keil

  DOI：10.1021/ja0686211

  日期：2007.3.1

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.