trans-7-(4S-hydroxyhept-2-enoic acid methyl ester)carbamic acid tert-butyl ester | 1203455-26-8

• 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: trans-7-(4S-hydroxyhept-2-enoic acid methyl ester)carbamic acid tert-butyl ester
• 英文别名: methyl (E,4S)-4-hydroxy-7-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate
• CAS: 1203455-26-8
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: JWWUHNRJVFELTK-JARNTUPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 tert-butyl N-(3-hydroxy-4-oxobutyl)carbamate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 15.5h， 生成 trans-7-(4S-hydroxyhept-2-enoic acid methyl ester)carbamic acid tert-butyl ester 、 trans-7-(4R-hydroxyhept-2-enoic acid methyl ester)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone

  摘要：

  The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally Occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.

  DOI：

  10.1021/jo902396m

文献信息

• Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone
  作者：Noel P. McLaughlin、Paul Evans

  DOI：10.1021/jo902396m

  日期：2010.1.15

  The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally Occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.