syn-2,3-3-hydroxy-2-methyl-pent-4-enoic acid | 113564-12-8

• 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: syn-2,3-3-hydroxy-2-methyl-pent-4-enoic acid
• 英文别名: scalemic acid；(2R,3S)-3-hydroxy-2-methylpent-4-enoic acid
• CAS: 113564-12-8
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: LEMWLUVPJFUNEB-UHNVWZDZSA-N

物化性质

• 沸点：
  259.8±28.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-2,3-3-hydroxy-2-methyl-pent-4-enoic acid 在 platinum(IV) oxide 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (2R,6R)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptanol
  参考文献：
  名称：

  Acyclic stereoselection. Part 42. 1,4- and 1,5-Stereoselection by sequential aldol addition to a .alpha.,.beta.-unsaturated aldehydes followed by Claisen rearrangement. Application to total synthesis of the vitamin E side chain and the archaebacterial C40 diol

  摘要：

  DOI：

  10.1021/jo00244a017
• 作为产物：
  描述：

  (4R^*,5S^*)-5-hydroxy-2,4-dimethyl-2-<(trimethylsilyl)oxy>-6-hepten-3-one 生成 syn-2,3-3-hydroxy-2-methyl-pent-4-enoic acid
  参考文献：
  名称：

  HEATHCOCK, CLAYTON H.;FINKELSTEIN, BRUCE L.;JARVI, ESA T.;RADEL, PEGGY A.+, J. ORG. CHEM., 53,(1988) N 9, 1922-1942

  摘要：

  DOI：

文献信息

• d-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions
  作者：Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(97)00096-7

  日期：1997.4

  Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.