tert-butyl ((4S,6S)-6-hydroxyhept-1-en-4-yl)carbamate | 1416569-37-3

• 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: tert-butyl ((4S,6S)-6-hydroxyhept-1-en-4-yl)carbamate
• 英文别名: tert-butyl N-[(4S,6S)-6-hydroxyhept-1-en-4-yl]carbamate
• CAS: 1416569-37-3
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: DMXZPCKSOVTVEY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl ((4S,6S)-6-hydroxyhept-1-en-4-yl)carbamate 在 咪唑 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 2,2'-双(二苯基磷)联苯 、 4,6-二(二苯基膦)吩嗪 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 (S)-tert-butyl 2-((S)-2-((tert-butyldimethylsilyl)oxy)propyl)-3,4-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde

  摘要：

  The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.

  DOI：

  10.1021/ol302769r
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2S,4S)-4-aminohept-6-en-2-ol 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 24.5h， 以0.41 g的产率得到tert-butyl ((4S,6S)-6-hydroxyhept-1-en-4-yl)carbamate
  参考文献：
  名称：

  Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde

  摘要：

  The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.

  DOI：

  10.1021/ol302769r

文献信息

• Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde
  作者：Hong Ren、William D. Wulff

  DOI：10.1021/ol302769r

  日期：2013.1.18

  The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.