α-(1-Hydroxy-2-methylpropyl)benzenessigsaeure-methylester | 19901-81-6

• 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-methylpropyl)benzenessigsaeure-methylester
• 英文别名: anti-methyl 3-hydroxy-4-methyl-2-phenylpentanoate；methyl anti-3-hydroxy-4-methyl-2-phenylpentanoate；methyl (2S,3S)-3-hydroxy-4-methyl-2-phenylpentanoate
• CAS: 19901-81-6；33398-48-0
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: YDFPBPDMGCKVEU-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  甲基碘化镁 、 α-(1-Hydroxy-2-methylpropyl)benzenessigsaeure-methylester 生成
  参考文献：
  名称：

  Internal solvation effects on the conformation of acyclics

  摘要：

  DOI：

  10.1016/s0040-4020(01)91604-7
• 作为产物：
  描述：

  异丁醛 、 苯乙酸甲酯 在 三乙胺 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以86%的产率得到α-(1-Hydroxy-2-methylpropyl)benzenessigsaeure-methylester
  参考文献：
  名称：

  Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

  摘要：

  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.

  DOI：

  10.1021/ol301782s

文献信息

• Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
  作者：Mija Ahn、Kiyoshi Tanaka、Kaoru Fuji

  DOI：10.1039/a706673b

  日期：——

  Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

  已研究了2′-羟基-1,1′-联萘酯酮烯与多种羰基电烯的醇醛反应和结合加成反应中的二面体选择性。由BuLi生成的酯酮烯与几种醛反应，优先生成threo产物，具有高的二面体选择性和良好的收率。在少量的erythro衍生物中也观察到了令人满意的二面体选择性。根据产物的绝对立体化学，对结果进行了机制解释。
• 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.
• Mulzer, Johann; Bruentrup, Gisela, Chemische Berichte, 1982, vol. 115, # 6, p. 2057 - 2075
  作者：Mulzer, Johann、Bruentrup, Gisela

  DOI：——

  日期：——
• 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.
• 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