(4S,5S)-dec-1-ene-4,5-diol | 1372769-26-0

• 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: (4S,5S)-dec-1-ene-4,5-diol
• CAS: 1372769-26-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: GBGKMGHDXFBMOP-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-dec-1-ene-4,5-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 柠檬酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 11.0h， 生成 (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u
• 作为产物：
  描述：

  4-戊烯醛 在 CeCl₃*LiCl 、 D-脯氨酸 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 18.17h， 生成 (4S,5S)-dec-1-ene-4,5-diol
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u

文献信息

• An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from <i>Notheia anomala</i>
  作者：Sudeshna Roy、Christopher D. Spilling

  DOI：10.1021/ol300597u

  日期：2012.5.4

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.