(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one | 70670-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one
• 英文别名: (E,3S,5R)-3,5-dihydroxy-7-phenyl-6-heptenoic acid 1,5-lactone；(3S,5R,6E)-3-hydroxy-7-phenyl-6-hepten-5-olide；(4S,6R)-4-hydroxy-6-[(E)-2-phenylethenyl]oxan-2-one
• CAS: 70670-14-3
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: LATSAVAHDMSYNE-KZQRZKTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到(6R)-(+)-5,6-二氢-6-苯乙烯基-2-吡喃酮
  参考文献：
  名称：

  Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.

  摘要：

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。

  DOI：

  10.1248/cpb.42.839
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-D-glucose 在 Amberlit IR 120 resin (H⁺ form) 吡啶 、 sodium hydroxide 、 重铬酸吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 dimsylsodium 、 水 、 双氧水 、 sodium iodide 、 锌 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one
  参考文献：
  名称：

  Gillard, Frederic; Heissler, Denis; Riehl, Jean-Jacques, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2291 - 2296

  摘要：

  DOI：

文献信息

• Stereoselective Reduction of<i>β</i>,<i>δ</i>-Diketo Esters. A Novel Strategy for the Synthesis of Artificial HMG-CoA Reductase Inhibitors
  作者：Tamejiro Hiyama、Guntoori Bhaskar Reddy、Tatsuya Minami、Takeshi Hanamoto

  DOI：10.1246/bcsj.68.350

  日期：1995.1

  Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe–NaBH4 in tetrahydrofuran–methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber’s chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber’s chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe–NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

  N-甲氧基-N-甲基酰胺与乙酰乙酸酯的二阴离子缩合，高产率地得到了β，δ-二酮酯，这些二酮酯在四氢呋喃-甲醇中与Et2BOMe-NaBH4还原，高度选择性地一步得到syn-β，δ-二羟基酯。类似地，Taber的手性醇或其对映体的β，δ-二酮酯分别还原得到中等对映体纯度的syn-β,δ-二羟基酯。通过先后使用二异丁基铝烷和Et2BOMe-NaBH4还原Taber的手性醇或其对映体的β,δ-二酮酯，获得了更高的非对映选择性和对映选择性。得到的syn-二醇酯经水解和内酯化得到多种常见于人工HMG-CoA还原酶抑制剂中的β-羟基-δ-内酯。
• Syntheses of argentilactone 11 and Goniothalamin 15
  作者：Brian O'Connor、George Just

  DOI：10.1016/s0040-4039(00)85168-0

  日期：——
• Enantioselective synthesis of .beta.-hydroxy .delta.-lactones: a new approach to the synthetic congeners of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors
  作者：G. Bhaskar Reddy、Tatsuya Minami、Takeshi Hanamoto、Tamejiro Hiyama

  DOI：10.1021/jo00020a008

  日期：1991.9

  Chiral beta,delta-diketo esters derived from Taber's chiral alcohol or its enantiomer were reduced either in one step (Et2BOMe, NaBH4, THF-MeOH) or in two steps (2 equiv HAl(i-Bu)2, THF; Et2BOMe, NaBH4, THF-MeOH) to give syn-beta,delta-dihydroxy esters with high diastereoselectivity. Hydrolysis of the esters followed by lactonization afforded the title lactones of high optical purity ranging from 49 to > 97% ee.
• Enzyme-catalyzed lactonization of methyl (±)-(E)-3,5-dihydroxy-7-phenyl-6-heptenoates. - A comparison of the behaviour of syn- and anti-compounds
  作者：Birgitta Henkel、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0957-4166(00)82325-3

  日期：1993.2

  3-Hydroxy lactones with a high enantiomeric excess were obtained by the lipase-catalyzed enantioselective lactonization of racemic syn- and anti-3,5-dihydroxy carboxylic esters. The (5S)-lactones were formed predominantly from both diols with pancreatin as enzyme. The lipase from Candida sp. 382, however, catalyzed the preferential formation of the (5S)-lactone only from the syn-diol. From the anti-diol the (5R)-lactone was formed as the main enantiomer.
• KAPA, PRASAD K.
  作者：KAPA, PRASAD K.

  DOI：——

  日期：——