methyl syn-(E)-3-hydroxy-2,5-diphenylpent-4-enoate

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl syn-(E)-3-hydroxy-2,5-diphenylpent-4-enoate
• 英文别名: syn-(E)-methyl 3-hydroxy-2,5-diphenylpent-4-enoate；methyl (E,2S,3R)-3-hydroxy-2,5-diphenylpent-4-enoate
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: OVWAPEBYKRUDEE-DCVVVBLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  反式肉桂醛 、 苯乙酸甲酯 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.25h， 以80%的产率得到
  参考文献：
  名称：

  Overriding effect of temperature over reagent and substrate size for boron-mediated aldol reaction of methyl phenylacetate

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.08.106

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。
• 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.