(4R,5S)-4-nitrodec-1-en-5-ol | 1447839-93-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (4R,5S)-4-nitrodec-1-en-5-ol
• CAS: 1447839-93-1
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: PIBBVLLDMUPAPK-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-nitrodec-1-en-5-ol 在 palladium 10% on activated carbon 、 氢气 、 四丁基醋酸铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 5.25h， 生成 (6S,8R)-8-hydroxy-6-[(1S)-1-hydroxyhexyl]-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
  参考文献：
  名称：

  Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine

  摘要：

  We previously reported the synthesis of the 1,N-2-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of O-6-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.(6) An improved synthesis of the amino triols has been developed. The syn and anti diastereomers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO4 and a tertiary amine oxide as the stoichiometric oxidant led to scrambling of stereochemistry of the nitro group. The scrambling was not observed when t-butylhydroperoxide was used as the oxidant. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.004
• 作为产物：
  描述：

  4-nitrobut-1-ene 、 正己醛 在 四丁基氯化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (4S,5S)-4-nitrodec-1-en-5-ol 、 (4R,5R)-4-nitrodec-1-en-5-ol 、 (4S,5R)-4-nitrodec-1-en-5-ol 、 (4R,5S)-4-nitrodec-1-en-5-ol
  参考文献：
  名称：

  Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine

  摘要：

  We previously reported the synthesis of the 1,N-2-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of O-6-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.(6) An improved synthesis of the amino triols has been developed. The syn and anti diastereomers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO4 and a tertiary amine oxide as the stoichiometric oxidant led to scrambling of stereochemistry of the nitro group. The scrambling was not observed when t-butylhydroperoxide was used as the oxidant. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.004

文献信息

• Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine
  作者：Plamen P. Christov、Edward K. Hawkins、Nathan R. Kett、Carmelo J. Rizzo

  DOI：10.1016/j.tetlet.2013.06.004

  日期：2013.8

  We previously reported the synthesis of the 1,N-2-deoxyguanosine adducts of 4-hydroxynonenal, an important product of lipid peroxidation, which involved the nucleophilic aromatic substitution reaction of O-6-protected-2-fluoroinosine with 4-amino-1,2,5-trihydroxydecanal followed by periodate oxidation of the vicinal diol.(6) An improved synthesis of the amino triols has been developed. The syn and anti diastereomers of a key intermediate, 4-nitro-5-hydroxy-1-decene, were synthesized by a Henry reaction and separated; each diastereomer was further separated into individual enantiomers by chiral supercritical fluid chromatography. Of note, dihydroxylation of the terminal olefin under conventional conditions with catalytic OsO4 and a tertiary amine oxide as the stoichiometric oxidant led to scrambling of stereochemistry of the nitro group. The scrambling was not observed when t-butylhydroperoxide was used as the oxidant. (C) 2013 Elsevier Ltd. All rights reserved.