(2SR)-2-<(2RS)-5,6-dihydro-2H-pyranyl>propanoic acid | 86611-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2SR)-2-<(2RS)-5,6-dihydro-2H-pyranyl>propanoic acid
• 英文别名: (2SR)-2-[(2RS)-5,6-dihydro-2H-pyranyl]propanoic acid；(2R)-2-[(6S)-3,6-dihydro-2H-pyran-6-yl]propanoic acid
• CAS: 86611-36-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: BXSIBZPBKZAPRB-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2H-吡喃-4(3H)-酮 在 吡啶 、 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 二异丙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.67h， 生成 (2SR)-2-<(2RS)-5,6-dihydro-2H-pyranyl>propanoic acid
  参考文献：
  名称：

  Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection

  摘要：

  The preference for chair- and boatlike transition-state geometries in the ester enolate Claisen rearrangement of straight chain, carbocyclic, and heterocyclic propanoates was investigated. A novel stereoelectronic effect in pyranoid and furanoid glycal systems leads to a significant relative stabilization of the boatlike vs the chairlike TS double-ended-dagger. The preferred transition state in six- and five-membered carbocyclic systems is highly dependent on steric factors, as the energy difference between chair- and boatlike TS double-ended-dagger tends to be small. With straight-chain substrates, a significant contribution of the boatlike TS double-ended-dagger to the rearrangement product mixture is only expected in bis-donor substituted allylic esters.

  DOI：

  10.1021/jo00011a023

文献信息

• Formal total synthesis of (.+-.)-pseudomonic acids A and C. The quasi-intramolecular Lewis acid catalyzed Diels-Alder reaction
  作者：Barry B. Snider、Gary B. Phillips、Robert Cordova

  DOI：10.1021/jo00166a013

  日期：1983.9
• Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection
  作者：Robert E. Ireland、Peter Wipf、Jia Ning Xiang

  DOI：10.1021/jo00011a023

  日期：1991.5

  The preference for chair- and boatlike transition-state geometries in the ester enolate Claisen rearrangement of straight chain, carbocyclic, and heterocyclic propanoates was investigated. A novel stereoelectronic effect in pyranoid and furanoid glycal systems leads to a significant relative stabilization of the boatlike vs the chairlike TS double-ended-dagger. The preferred transition state in six- and five-membered carbocyclic systems is highly dependent on steric factors, as the energy difference between chair- and boatlike TS double-ended-dagger tends to be small. With straight-chain substrates, a significant contribution of the boatlike TS double-ended-dagger to the rearrangement product mixture is only expected in bis-donor substituted allylic esters.