t-butyl (2R,3R)-1-benzyl-3-isopropenylaziridine-2-carboxylate | 871259-04-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl (2R,3R)-1-benzyl-3-isopropenylaziridine-2-carboxylate
• 英文别名: tert-butyl (2R,3R)-1-benzyl-3-prop-1-en-2-ylaziridine-2-carboxylate
• CAS: 871259-04-0
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: VXXMBMUKBYRQQZ-QOYAAKSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  t-butyl (2R,3R)-1-benzyl-3-isopropenylaziridine-2-carboxylate 在 palladium on activated charcoal 水 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 30.0h， 生成 (2R,3S)-3-Hydroxyleucine t-butyl ester
  参考文献：
  名称：

  Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2R,3S)-3-Hydroxyleucinate and d-erythro-Sphingosine

  摘要：

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.

  DOI：

  10.1021/jo051495j
• 作为产物：
  描述：

  2-甲基丙烯醛 、 Benzyl-tert-butoxycarbonylmethyl-((4S,5S)-1,3-dimethyl-4,5-diphenyl-imidazolidin-2-ylidene)-ammonium; bromide 在 四甲基胍 、 silica gel 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 144.0h， 生成 t-butyl (2S,3R)-1-benzyl-3-isopropenylaziridine-2-carboxylate 、 t-butyl (2S,3S)-1-benzyl-3-isopropenylaziridine-2-carboxylate 、 t-butyl (2R,3R)-1-benzyl-3-isopropenylaziridine-2-carboxylate 、 t-butyl (2R,3S)-1-benzyl-3-isopropenylaziridine-2-carboxylate
  参考文献：
  名称：

  Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2R,3S)-3-Hydroxyleucinate and d-erythro-Sphingosine

  摘要：

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.

  DOI：

  10.1021/jo051495j

文献信息

• Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2<i>R</i>,3<i>S</i>)-3-Hydroxyleucinate and <scp>d</scp>-<i>e</i><i>rythro</i>-Sphingosine
  作者：Wannaporn Disadee、Tsutomu Ishikawa

  DOI：10.1021/jo051495j

  日期：2005.11.1

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.