anti-5-Hydroxy-4,6,6-trimethyl-3-heptanone | 81640-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: anti-5-Hydroxy-4,6,6-trimethyl-3-heptanone
• 英文别名: (4R,5S)-5-hydroxy-4,6,6-trimethylheptan-3-one
• CAS: 81640-11-1；81640-12-2；100483-72-5
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: GWYAABORNPETPL-CBAPKCEASA-N

物化性质

• 沸点：
  245.7±13.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  特戊醛 、 3-戊酮 在 titanium(IV) isopropylate 、 苯基溴化镁 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以78%的产率得到anti-5-Hydroxy-4,6,6-trimethyl-3-heptanone
  参考文献：
  名称：

  Stereoselective aldol reaction using titanium ate complexes -an efficient method for achieving anti aldol selectivity

  摘要：

  Carbonyl compounds react in the presence of titanium ate complexes in the sense of an aldol reaction. The influence of ligands on controlling stereoselection of syn and anti aldol products of the titanium ate complexes used are described. High yield of anti aldol products was observed by using sterically hindered aliphatic aldehydes.

  DOI：

  10.1016/0040-4020(95)00496-u

文献信息

• Ytterbium Trifluoromethanesulfonate Mediated Cross-Aldol Reaction between Ketones and Aldehydes
  作者：Shin-ichi Fukuzawa、Teruhisa Tsuchimoto、Takeshi Kanai

  DOI：10.1246/bcsj.67.2227

  日期：1994.8

  The cross-aldol reaction between a ketone and an aldehyde proceeded smoothly with threo diastereoselection favorably mediated by ytterbium trifluoromethanesulfonate and tertiary amine in diethyl ether or in dichloromethane. A ytterbium enolate was trapped with chlorotrimethylsilane to afford a silyl enol ether.

  在二乙醚或二氯甲烷中，通过三氟甲磺酸镱和叔胺的介导，酮和醛之间的交叉羟醛反应顺利进行，形成了具有良好立体选择性的threo异构体。通过用三甲基氯硅烷捕获镱烯醇盐，得到了烯醇硅醚产物。
• HIGHLY ENANTIOSELECTIVE SYNTHESIS OF<i>ANTI</i>(<i>THREO</i>)-ALDOLS BY THE ASYMMETRIC ALDOL REACTION UTILIZING A CHIRAL AZAENOLATE
  作者：Koichi Narasaka、Tetsuo Miwa

  DOI：10.1246/cl.1985.1217

  日期：1985.8.5

  Diastereo- and enantioselective aldol reaction between 3-pentanone and aldehydes is achieved utilizing a chiral oxazolidine derived from 3-pentanone and chiral norephedrine. The reaction of a tin(II) azaenolate generated from the chiral oxazolidine with aldehydes affords predominantly anti(threo)-aldols of high enantiomeric purity.

  利用衍生自 3-戊酮和手性去甲麻黄碱的手性恶唑烷实现 3-戊酮和醛之间的非对映选择性和对映选择性羟醛反应。由手性恶唑烷生成的锡 (II) 氮杂烯醇化物与醛的反应主要提供高对映体纯度的抗 (苏式)-羟醛。
• 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。
• Mahrwald, Rainer, Chemische Berichte, 1995, vol. 128, # 9, p. 919 - 922
  作者：Mahrwald, Rainer

  DOI：——

  日期：——
• Erythro selective aldol condensation using titanium enolates
  作者：M.T. Reetz、R. Peter

  DOI：10.1016/s0040-4039(01)83014-8

  日期：1981.1