3-(p-toluenesulfonyl)-2-pyrone | 99268-87-8

• 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: 3-(p-toluenesulfonyl)-2-pyrone
• 英文别名: 3-(p-tolylsulfonyl)-2-pyrone；3-p-toluenesulfonyl-2-pyrone；3-(4-Methylphenyl)sulfonylpyran-2-one
• CAS: 99268-87-8
• 化学式: C₁₂H₁₀O₄S
• 分子量: 250.275
• InChiKey: JTMBJYSMXZTNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(p-toluenesulfonyl)-2-pyrone 在 bis(2,6-di-tert-butyl-4-methylphenoxy)-methylaluminium 咪唑 、 甲醇 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 (1RS,3S,5R)-3,5-bis(t-butyldimethylsiloxy)-1-carboethoxymethyl-2-methylenecyclohexane
  参考文献：
  名称：

  Asymmetric total synthesis of an A-ring precursor to hormonally active 1.alpha.,25-dihydroxyvitamin D3

  摘要：

  DOI：

  10.1021/jo00300a001
• 作为产物：
  描述：

  4-甲基苯硫代磺酸 S-(4-甲基苯基)酯 在 lithium dimethylcuprate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 3-(p-toluenesulfonyl)-2-pyrone
  参考文献：
  名称：

  3-Cuprio-2-pyrone: an extraordinary organocopper reagent

  摘要：

  DOI：

  10.1021/jo00225a008

文献信息

• Inverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones
  作者：Yoshimitsu Hashimoto、Ryo Abe、Nobuyoshi Morita、Osamu Tamura

  DOI：10.1039/c8ob02132e

  日期：——

  of 3-electron-withdrawing group substituted α-pyrones with α,β-unsaturated hydrazones as electron-rich counterparts are catalyzed by Eu(hfc)3 to afford bicyclic lactone cycloadducts. This is an example of umpolung cycloaddition based on functional transformation of carbonyls to hydrazones. A subsequent dehydrazonation reaction enables indirect synthesis of carbonyl group-containing bicyclic lactones

  Eu（hfc）3催化3吸电子基团取代的α-吡喃酮与富电子的α，β-不饱和酮的反电子需求Diels-Alder反应，由Eu（hfc）3催化，得到双环内酯环加合物。这是基于羰基向to的功能转化的环酚加成的例子。随后的脱水反应使得能够间接合成含羰基的双环内酯，而这是不容易通过α-吡喃酮和烯醛的环加成而获得的。
• Stereocontrolled synthesis of highly functionalized cyclohexenes. A short synthesis of a chorismic acid precursor
  作者：Gary H. Posner、Todd D. Nelson

  DOI：10.1016/s0040-4020(01)85582-4

  日期：——

  allowing isolation of the structurally and stereochemically rich initial bicyclic adducts 8. These bicyclic adducts are shown to be useful building units as exemplified by a very short and high-yield preparation of a chorismic acid precursor.

  已经开发了一种方便且温和的热方法，可将富电子的1,2-二加氧烯烃7立体选择性2 + 4-环加成至缺电子的3-磺酰基-2-吡喃酮6，从而可以分离结构和立体化学丰富的初始双环加合物8。这些双环加合物被证明是有用的结构单元，例如以短而高收率制备的鸟苷酸前体为例。
• Stereocontrolled Total Synthesis of Calcitriol Derivatives: 1,25-Dihydroxy-2-(4'-hydroxybutyl)vitamin D3 Analogs of an Osteoporosis Drug
  作者：Gary H. Posner、Neil Johnson

  DOI：10.1021/jo00104a050

  日期：1994.12

  The diastereomeric 2 alpha- and 2 beta-(4'-hydroxybutyl) calcitriol analogs (-)-3 and (+)-3' were prepared in only 11 chemical operations, starting with 4 + 2-cycloaddition of commercially available methyl 2-pyrone-3-carboxylate. Highlights of this convergent and stereocontrolled synthetic approach are as follows: (1) retention of reactant dienophile geometry in the product bicyclic lactone, characteristic of a concerted inverse-electron-demand Diels-Alder cycloaddition; (2) an improved decarboxylation procedure involving chemospecific allyloxide opening of a lactone ring in the presence of a methyl ester and then non-high pressure palladium-promoted allylic ester decarboxylation; and (3) use of the enantiomercially pure C,D-ring chiron (+)-14 to resolve racemic A-ring phosphine oxide (+/-)-13. Relative binding affinities of the enantiomerically pure diastereomers (-)-3 and (+)-3' to the vitamin D binding protein and to the vitamin D receptor showed some unexpected trends. Diastereomer (+)-3' surprisingly bound more effectively to the vitamin D receptor than did the established osteoporosis drug ED-71 (1).
• Asymmetric Diels-Alder cycloadditions using chiral alkyl vinyl ethers and a dienyl sulfone
  作者：Gary H. Posner、David G. Wettlaufer

  DOI：10.1016/s0040-4039(00)84068-x

  日期：1986.1
• POSNER, G. H.;HARRISON, W.;WETTLAUFER, D. G., J. ORG. CHEM., 1985, 50, N 25, 5041-5044
  作者：POSNER, G. H.、HARRISON, W.、WETTLAUFER, D. G.

  DOI：——

  日期：——