(2SR,3RS,4SR)-phenyl-3-hydroxy-2-methylpentanoic acid | 72523-87-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2SR,3RS,4SR)-phenyl-3-hydroxy-2-methylpentanoic acid
• 英文别名: (2R,3S,4R)-3-hydroxy-2-methyl-4-phenylpentanoic acid
• CAS: 72523-87-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: AHDKNAOKCZADTH-KKZNHRDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2SR,3RS,4SR)-phenyl-3-hydroxy-2-methylpentanoic acid 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 生成 Methyl (2R^*,3S^*,4R^*)-3-hydroxy-2-methyl-4-phenylvalerate
  参考文献：
  名称：

  Shinzer, Dieter, Synthesis, 1989, # 3, p. 179 - 181

  摘要：

  DOI：
• 作为产物：
  描述：

  (3SR,5SR,6RS,7SR)-7-phenyl-6-hydroxy-2,2,5-trimethyl-3-<(trimethylsilyl)oxy>octan-4-one 在 高碘酸 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到(2SR,3RS,4SR)-phenyl-3-hydroxy-2-methylpentanoic acid
  参考文献：
  名称：

  Acyclic stereoselection. 12. Double stereodifferentiation with mutual kinetic resolution. A superior class of reagents for control of Cram's rule stereoselection in synthesis of erythro-.alpha.-alkyl-.beta.-hydroxy carboxylic acids from chiral aldehydes

  摘要：

  DOI：

  10.1021/jo00324a017

文献信息

• Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters
  作者：Cesare Gennari、Anna Bernardi、Silvia Cardani、Carlo Scolastico

  DOI：10.1016/0040-4020(84)85086-3

  日期：1984.1

  dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products. The thioester additions to chiral aldehydes were studied. Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used. The aldol products were transformed to known compounds for correlation

  进行了详细的研究，将硫代丙酸苯基酯与亚乙基氯硼酸酯（ECB）和二异丙基乙胺（DPEA）进行烯醇化，随后对这些烯醇化物进行醇醛缩合反应。已发现衍生自硫酯的烯氧基二烷氧基硼烷是立体收敛的：Z和E的烯醇盐均生成顺式醇醛缩合产物。研究了手性醛中硫代酯的添加。内部选择性（syn）通常很高，而相对的立体选择性则根据所使用的特定醛的不同，从差到好。将醛醇缩合产物转化为已知化合物以进行相关。
• Stereochemical consequences of the Lewis acid catalyzed cyclocondensation of oxygenated dienes with aldehydes. A rapid and stereoselective entry to various natural products derived from propionate
  作者：Samuel Danishefsky、Nobuo Kato、David Askin、James F. Kerwin

  DOI：10.1021/ja00365a096

  日期：1982.1
• Acyclic stereoselection. 6. A reagent for achieving high 1,2-diastereoselection in the aldol conversion of chiral aldehydes into 3-hydroxy-2-methylcarboxylic acids
  作者：Clayton H. Heathcock、Michael C. Pirrung、Charles T. Buse、James P. Hagen、Steven D. Young、John E. Sohn

  DOI：10.1021/ja00517a056

  日期：1979.11
• HEATHCOCK C. H.; PIRRUNG M. C.; LAMPE J.; BUSE C. T.; YOUNG S. D., J. ORG. CHEM., 1981, 46, NO 11, 2290-2300
  作者：HEATHCOCK C. H.、 PIRRUNG M. C.、 LAMPE J.、 BUSE C. T.、 YOUNG S. D.

  DOI：——

  日期：——
• GENNARI, C.;BERNARDI, A.;CARDANI, S.;SCOLASTICO, C., TETRAHEDRON, 1984, 40, N 20, 4059-4065
  作者：GENNARI, C.、BERNARDI, A.、CARDANI, S.、SCOLASTICO, C.

  DOI：——

  日期：——