(3S,4Z,6S)-2,7-dimethyl-4-octene-3,6-diol | 487059-56-3

• 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: (3S,4Z,6S)-2,7-dimethyl-4-octene-3,6-diol
• 英文别名: (Z,3S,6S)-2,7-dimethyloct-4-ene-3,6-diol
• CAS: 487059-56-3
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: RXKPKYYHNKGKOT-KWMOZEJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  (3S,4Z,6S)-2,7-dimethyl-4-octene-3,6-diol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium chlorite 、 sodium dihydrogenphosphate 、 萘 、 三异丙基亚磷酸酯 、 双氧水 、 sodium 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 (4S,5S)-5-Isopropyl-2-oxazolidinone-4-carboxylic acid
  参考文献：
  名称：

  Stereodivergent Approach to β-Hydroxy α-Amino Acids from C₂-Symmetrical Alk-2-yne-1,4-diols

  摘要：

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

  DOI：

  10.1021/ol0270428
• 作为产物：
  描述：

  2,7-dimethyl-4-octyne-3,6-diol 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以97%的产率得到(3S,4Z,6S)-2,7-dimethyl-4-octene-3,6-diol
  参考文献：
  名称：

  Stereodivergent Approach to β-Hydroxy α-Amino Acids from C₂-Symmetrical Alk-2-yne-1,4-diols

  摘要：

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

  DOI：

  10.1021/ol0270428

文献信息

• Stereodivergent Approach to β-Hydroxy α-Amino Acids from <i>C</i>₂-Symmetrical Alk-2-yne-1,4-diols
  作者：Marta Amador、Xavier Ariza、Jordi Garcia、Sara Sevilla

  DOI：10.1021/ol0270428

  日期：2002.12.1

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.