(4R,5S)-4,6-dimethyl-5-hydroxy-3-heptanone | 113626-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-4,6-dimethyl-5-hydroxy-3-heptanone
• 英文别名: (4R,5S)-5-hydroxy-4,6-dimethyl-3-heptanone；(4R,5S)-5-hydroxy-4,6-dimethylheptan-3-one
• CAS: 113626-45-2
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: BIEQEQORPVLGMS-CBAPKCEASA-N

物化性质

• 沸点：
  232.5±13.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (4R,5S)-4,6-dimethyl-5-hydroxy-3-heptanone 、 异丁醛 生成 (1R,2R,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate
  参考文献：
  名称：

  EVANS, DAVID A.;HOVEYDA, AMIR H., J. AMER. CHEM. SOC., 112,(1990) N7, C. 6447-6449

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-(tert-Butyldimethylsilyl)pentan-3-on 在 tetrafluoroboric acid 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (4R,5S)-4,6-dimethyl-5-hydroxy-3-heptanone
  参考文献：
  名称：

  Enders, Dieter; Lohray, Braj Bhushan, Angewandte Chemie, 1988, vol. 100, # 4, p. 594 - 596

  摘要：

  DOI：

文献信息

• Titanium(IV) Alkoxide Ligand Exchange with α-Hydroxy Acids:  The Enantioselective Aldol Addition
  作者：Rainer Mahrwald

  DOI：10.1021/ol0002727

  日期：2000.12.1

  Ligand exchange of titanium(IV) alkoxides with alpha-hydroxy acids presents an unexpected and novel approach to enantioselective aldol additions of aldehydes and ketones. The aldol products were isolated in a high degree of syn-diastereoselectivity. High enantioselectivities were observed by using simple optically pure alpha-hydroxy acids in this novel aldol addition.

  钛（IV）醇盐与α-羟基酸的配体交换为醛和酮的对映选择性羟醛加成提供了一种出乎意料的新颖方法。以高度的对非对映体选择性分离出羟醛产物。通过在这种新颖的醛醇缩合中使用简单的光学纯的α-羟基酸，观察到高对映选择性。
• Enantioselective aldol condensations: The use of ketone boron enolates with chiral ligands attached to boron.
  作者：Ian Paterson、M.Anne Lister、Cynthia K McClure

  DOI：10.1016/s0040-4039(00)85065-0

  日期：1986.1

  Aldol condensation between diethylketone and simple aldehydes using(lpc)2BOTf/iPr2NEt in CH2Cl2 gives syn-adducts in good ee (66–90%) and with high diastereoselectivity(≥90%). Other chiral dialkylboron triflate reagents examined give lower ees.

  使用（LPC）和二乙基醛简单之间的醛醇缩合2 BOTf /我镨2净在CH 2氯2给出顺式良好EE（66-90％）中，用高非对映选择性（≥90％）-adducts。检查的其他手性二烷基硼酸三氟甲磺酸盐试剂可提供较低的ee。
• 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
• Scope and Limitations of Chiral <i>B</i>-[3,5-Bis(trifluoromethyl)phenyl]oxazaborolidine Catalyst for Use in the Mukaiyama Aldol Reaction
  作者：Kazuaki Ishihara、Shoichi Kondo、Hisashi Yamamoto

  DOI：10.1021/jo001271v

  日期：2000.12.1

  A new chiral oxazaborolidine catalyst was prepared in situ from 3,5-bis(trifluoromethyl)phenylboron dichloride and N-(p-toluenesulfonyl)-(S)-tryptophan. This catalyst is much more active than Corey's original catalyst for the Mukaiyama aldol reaction of aldehydes with silyl enol ethers. The observed syn selectivities and re-face attack of silyl enol ethers on carbonyl carbon of aldehydes imply that the extended-transition state model is applicable.
• Insight into the mechanism of direct catalytic aldol addition mediated by ambifunctional titanium complexes
  作者：R. Mahrwald、B. Ziemer

  DOI：10.1016/s0040-4039(02)00822-5

  日期：2002.6

  X-Ray structure analysis of a titanium(IV) isopropoxide/mandelic acid complex provides an insight into the mechanism of this novel direct enantioselective aldol addition. The catalytic cycle mediated by the titanium(IV) alkoxide/mandelic acid complex is presented. (C) 2002 Elsevier Science Ltd. All rights reserved.