α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-methylester | 33398-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-methylester
• 英文别名: methyl syn-3-hydroxy-4, 4-dimethyl-2-phenylpentanoate；syn-methyl 3-hydroxy-4,4-dimethyl-2-phenylpentanoate；methyl (2S,3S)-3-hydroxy-4,4-dimethyl-2-phenylpentanoate
• CAS: 33398-50-4；33398-53-7；82545-54-8
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: NRNUOYQMBSNMKZ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 (E)-1-tert-butyl-2-phenylethene 、 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-methylester
  参考文献：
  名称：

  Mulzer, Johann; Bruentrup, Gisela, Chemische Berichte, 1982, vol. 115, # 6, p. 2057 - 2075

  摘要：

  DOI：

文献信息

• Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1021/ol301782s

  日期：2012.9.7

  Unlike the enolboration-aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl2, the reaction favors the anti-pathway at -78 degrees C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.
• Overriding effect of temperature over reagent and substrate size for boron-mediated aldol reaction of methyl phenylacetate
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1016/j.tetlet.2013.08.106

  日期：2013.10

  The enolization temperature overrides all other aspects, including the sterics of the alkyl group of the boron reagent and the alkoxy group of the ester during the enolboration-aldolization of phenylacetates. This study has led to the first n-Bu2BOTf-mediated anti-selective aldol reaction of an ester. (C) 2013 Elsevier Ltd. All rights reserved.
• Internal solvation effects on the conformation of acyclics
  作者：R.A. Auerbach、C.A. Kingsbury

  DOI：10.1016/s0040-4020(01)91604-7

  日期：1971.1