(R)-(-)-5-hydroxyhex-2-ynoic acid tert-butyl ester | 428816-95-9

• 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: (R)-(-)-5-hydroxyhex-2-ynoic acid tert-butyl ester
• 英文别名: tert-butyl (5R)-5-hydroxyhex-2-ynoate
• CAS: 428816-95-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: PHTNWCGJJGPEAT-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-5-hydroxyhex-2-ynoic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以99%的产率得到tert-butyl-(5R,)-5-hydroxyhexanoate
  参考文献：
  名称：

  TFA-catalyzed trimerization of R -(+)-6-methyl-tetrahydro-pyran-2-one

  摘要：

  The enantiomerically pure (greater than or equal to98% ec) title compound R-(+)-6-methyl-tetrahydro-pyran-2-one (R)-1 in the presence of traces of trifluoroacetic acid (TFA) converts into an equilibrium Mixture with its trimer 4 [(R)-1:4=20:80] corresponding to a DeltaGcongruent to-0.8 kcal mol(-1). The transformation can be followed by H-1 and C-13 NMR spectroscopy. The structure of 4 was established by chemical correlation with (R)-1 and its molecular weight determined via its colligative properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02281-x
• 作为产物：
  描述：

  叔丁基丙炔酸酯 、 (R)-(+)-环氧丙烷 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以87%的产率得到(R)-(-)-5-hydroxyhex-2-ynoic acid tert-butyl ester
  参考文献：
  名称：

  TFA-catalyzed trimerization of R -(+)-6-methyl-tetrahydro-pyran-2-one

  摘要：

  The enantiomerically pure (greater than or equal to98% ec) title compound R-(+)-6-methyl-tetrahydro-pyran-2-one (R)-1 in the presence of traces of trifluoroacetic acid (TFA) converts into an equilibrium Mixture with its trimer 4 [(R)-1:4=20:80] corresponding to a DeltaGcongruent to-0.8 kcal mol(-1). The transformation can be followed by H-1 and C-13 NMR spectroscopy. The structure of 4 was established by chemical correlation with (R)-1 and its molecular weight determined via its colligative properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02281-x