(4SR,5SR)-4-methyl-5-prop-2'-yl-δ-valerolactone

• 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: (4SR,5SR)-4-methyl-5-prop-2'-yl-δ-valerolactone
• 英文别名: 5(R*)-methyl-6(R*)-isopropyl-δ-valerolactone；(±)-(5R,6R)-6-isopropyl-5-methyltetrahydro-2H-pyran-2-one；(5S,6S)-5-Methyl-6-propan-2-yloxan-2-one
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: RORYOGLYWSZODQ-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4SR,5SR)-4-methyl-5-prop-2'-yl-δ-valerolactone 在 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (4R*,5R*)-4,6-dimethyl-5-((tert-butyldimethylsilyl)oxy)heptanal
  参考文献：
  名称：

  Synthesis of the branched nine-carbon unit of the type A streptogramins and other antibiotics

  摘要：

  DOI：

  10.1021/jo00277a047
• 作为产物：
  描述：

  2-{2-[乙基(甲基)氨基]乙基}-3-甲基-2-(1-萘基)丁醛 在 Rh on carbon 氢气 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 生成 (4SR,5SR)-4-methyl-5-prop-2'-yl-δ-valerolactone
  参考文献：
  名称：

  Synthesis of the branched nine-carbon unit of the type A streptogramins and other antibiotics

  摘要：

  DOI：

  10.1021/jo00277a047

文献信息

• Highly Stereoselective 2-Oxonia-Cope Rearrangement: A Platform Enabling At-Will Control of Regio-, Enantio-, and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes
  作者：Akhil Padarti、Dongeun Kim、Hyunsoo Han

  DOI：10.1021/acs.orglett.7b03895

  日期：2018.2.2

  the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without

  描述了一种用于乙烯醇醛缩醛醛的截然不同的方法，其在简单条件下利用了两个容易获得的伙伴，一组合理设计的手性均烯丙基醇合成子和醛之间的2-氧代-Cope重排反应。在这些过程中，手性从前者向后者的转移几乎是完美的，从而产生了出色的对映异构和非对映异构选择性，而没有与传统的乙烯基醛醇缩合反应相关的区域选择性问题。
• Stereochemistry of the reaction of Si–phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones
  作者：Mahesh J. Sanganee、Patrick G. Steel、Daniel K. Whelligan

  DOI：10.1039/b404175e

  日期：——

  silacycles accompanied by variable amounts of competing ene, [2 + 2] and silene dimer by-products. The silacycles are formed with good chemo- and stereo-selectivity and provide access to diols and lactones via a phenyl-triggered Fleming-Tamao oxidation.

  可以通过[4 + 2]环加成途径，通过一系列烷基丁二烯截留通过甲硅烷基修饰的Peterson烯烃化程序生成的硅，从而提供硅杂环化合物，并伴以不同量的竞争性烯，[2 + 2]和硅二聚体副产物。形成的silacycles具有良好的化学和立体选择性，并通过苯基触发的Fleming-Tamao氧化提供了与二醇和内酯的通道。
• A Study of Exocyclic Radical Reductions of Polysubstituted Tetrahydropyrans
  作者：François Godin、Michel Prévost、Frédérick Viens、Philippe Mochirian、Jean-François Brazeau、Serge I. Gorelsky、Yvan Guindon

  DOI：10.1021/jo400721e

  日期：2013.6.21

  Exocyclic radical reductions were thoroughly investigated in the context of the synthesis of polysubstituted tetrahydropyrans, Which are found in numerous macrolides. The radical precursors studied herein were generated by tandem cycloetherification and iodoetherification reactions or, alternatively, by semicyclic acetals substitutions. DFT calculations (BHandHLYP/TZVP) performed at the transition-state level for the hydrogen radical delivery are in good accordance with the experimental data and enabled the identification of important conformational factors that govern the selectivities obtained. This study demonstrates:that both the preferred reactive conformation of the radical and steric interactions with the incoming hydride have to be considered in order to fully rationalize the levels of diastereoselection generated in acyclic free-radical processes.
• A new C2 chiral secondary amine
  作者：James K. Whitesell、Mark A. Minton、Kuo Ming Chen

  DOI：10.1021/jo00257a042

  日期：1988.10
• WHITESELL, J. K.;MINTON, M. A.;CHEN, KUO-MING, J. ORG. CHEM., 53,(1988) N 22, C. 5383-5384
  作者：WHITESELL, J. K.、MINTON, M. A.、CHEN, KUO-MING

  DOI：——

  日期：——