(S)-3-hydroxy-3,4,4-trimethyldihydrofuran-2(3H)-one | 272449-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-3-hydroxy-3,4,4-trimethyldihydrofuran-2(3H)-one
• 英文别名: (S)-α-methyl pantolactone；2(3H)-Furanone, dihydro-3-hydroxy-3,4,4-trimethyl-, (3S)-；(3S)-3-hydroxy-3,4,4-trimethyloxolan-2-one
• CAS: 272449-21-5
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: HHGQUUWGXWZKGA-SSDOTTSWSA-N

物化性质

• 沸点：
  225.6±15.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-3-hydroxy-3,4,4-trimethyldihydrofuran-2(3H)-one 、 (+/-)-N-trifluoroacetyl pipecolic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以60%的产率得到(S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol

  摘要：

  Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-alpha-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00304-5
• 作为产物：
  描述：

  (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester 生成 (S)-3-hydroxy-3,4,4-trimethyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary

  摘要：

  A dynamic kinetic resolution of racemic N-phthalyl amino acids by stereoselective esterification was examined using (S)-alpha-methylpantolactone as the chiral auxiliary. The reaction of various racemic N-phthalyl amino acids with this chiral alcohol in the presence of both DCC and DMAP afforded predominantly the (S,S)-esters in nearly quantitative yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00017-3

文献信息

• Highly Homogeneous Stereocontrolled Construction of Quaternary Hydroxyesters by Addition of Dimethylzinc to α-Ketoesters Promoted by Chiral Perhydrobenzoxazines and B(OEt)3
  作者：Rebeca Infante、Javier Nieto、Celia Andrés

  DOI：10.1002/chem.201102913

  日期：2012.4.2

  A highly efficient enantioselective addition of Me2Zn to α‐ketoesters, assisted by a chiral perhydro‐1,3‐benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α‐hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α‐ketoesters

  描述了在手性过氢-1,3-苯并恶嗪配体的协助下，高效地将Me 2 Zn对映体选择性地添加到α-酮酸酯中。这种新型的催化体系在制备具有季立体中心的α-羟基酯时，提供了均相的提高的对映选择性，当使用芳族，杂芳族或脂族α-酮酯时，对电子和空间效应的依赖性较小。催化剂可被回收和再利用而不会损失活性。