(R)-4-hydroxy-5-methyl-5-hexen-2-one | 123072-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-hydroxy-5-methyl-5-hexen-2-one
• 英文别名: (4R)-4-Hydroxy-5-methylhex-5-en-2-one
• CAS: 123072-84-4
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: LKGOBWHJXOZFIA-SSDOTTSWSA-N

物化性质

• 沸点：
  220.5±20.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-hydroxy-5-methyl-5-hexen-2-one 、 碘 生成 (4R,5R)-4,5-dihydroxy-6-iodo-5-methylhexan-2-one
  参考文献：
  名称：

  CHAMBERLIN, A. R.;DEZUBE, M.;DUSSAULT, P.;MCMILLS, M. C., J. AMER. CHEM. SOC., 1983, 105, N 18, 5819-5825

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基丙烯醛 、 (1S)-N-(1-methylethylidene)-1-phenylethylamine 在 双氧水 、 (+)-diisopinocampheylboron triflate 作用下， 生成 (R)-4-hydroxy-5-methyl-5-hexen-2-one 、 N-(1-(2-萘酚))磷脂酰基乙醇胺
  参考文献：
  名称：

  Mechanistic insights from ab initio calculations on a nitrogen analogue of the boron-mediated aldol reaction

  摘要：

  Molecular orbital calculations were used to study a nitrogen analogue of the boron mediated aldol reaction. Experimental results show that high selectivity can be obtained in some cases, at the cost of low yields. The molecular orbital calculations are used to analyse the experimental results and to suggest modifications to the experimental procedure. The results suggest an explanation for a puzzling reversal of selectivity in the aldol reactions of methyl ketones.

  DOI：

  10.1016/0040-4020(95)00170-d

文献信息

• Enantio- and diastereoselective aldol reactions of achiral ethyl and methyl ketones with aldehydes: the use of enol diisopinocampheylborinates
  作者：Ian Paterson、Jonathan M. Goodman、M. Anne Lister、Russell C. Schumann、Cynthia K. McClure、Roger D. Norcross

  DOI：10.1016/s0040-4020(01)85588-5

  日期：1990.1

  from achiral ethyl and methyl ketones by enolisation in the presence of tertiary amine bases (iPr2NEt or Et3N), undergo enantio- and diastereoselective aldol reactions with aldehydes. The reagents employed, (+)- and (-)-(Ipc)2BOTf, are easily prepared in enantiomerically pure form in two steps from (-)- and (+)-α-pinene, respectively. The aldol reaction between ethyl ketones and aldehydes using (+)- or

  通过在叔胺碱（i Pr 2 NEt或Et 3 N）存在下进行烯醇化而衍生自非手性乙基和甲基酮的烯醇二异opinocampheylborinates与醛进行对映和非对映选择性醛醇缩合反应。（+）-和（-）-（Ipc）2 BOTf所用的试剂易于分别从（-）-和（+）-α-pine烯分两步以对映体纯形式制备。使用（+）-或（-）-（Ipc）2 BOTf / i Pr 2 NEt在二氯甲烷中的乙酮与醛之间的醛醇缩合反应，通过衍生的手性Z-烯醇硼酸酯得到syn对映体过量（66-93％ee）和非对映选择性高（> -95％）的-α-甲基-β-羟基酮。相反，二乙基酮经由异构的E-烯醇二异松香樟脑硼酸酯（通过用（-）-（Ipc）2 BCl烯醇化）与甲基丙烯醛的抗选择性醛醇缩合反应的对映选择性可忽略不计。在与醛甲基酮的醛醇缩合反应的三氟甲磺酸酯和氯化试剂二者的使用提供了在中等对映体过量在醛的选择性enanti
• Aldol reactions of methylketones using chiral boron reagents: A reversal in aldehyde enantioface selectivity
  作者：Ian Paterson、Jonathan M. Goodman

  DOI：10.1016/s0040-4039(00)95300-0

  日期：1989.1
• Mechanistic insights from ab initio calculations on a nitrogen analogue of the boron-mediated aldol reaction
  作者：Anna Bernardi、Cesare Gennari、Jonathan M. Goodman、Volker Leue、Ian Paterson

  DOI：10.1016/0040-4020(95)00170-d

  日期：1995.4

  Molecular orbital calculations were used to study a nitrogen analogue of the boron mediated aldol reaction. Experimental results show that high selectivity can be obtained in some cases, at the cost of low yields. The molecular orbital calculations are used to analyse the experimental results and to suggest modifications to the experimental procedure. The results suggest an explanation for a puzzling reversal of selectivity in the aldol reactions of methyl ketones.
• CHAMBERLIN, A. R.;DEZUBE, M.;DUSSAULT, P.;MCMILLS, M. C., J. AMER. CHEM. SOC., 1983, 105, N 18, 5819-5825
  作者：CHAMBERLIN, A. R.、DEZUBE, M.、DUSSAULT, P.、MCMILLS, M. C.

  DOI：——

  日期：——