(E)-5-hydroxy-pent-3-en-2-one | 71197-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-hydroxy-pent-3-en-2-one
• 英文别名: allylic alcohol；5-hydroxy-pent-3t-en-2-one；trans-5-Hydroxy-3-penten-2-on；(E)-5-hydroxypent-3-en-2-one
• CAS: 71197-58-5
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: XPFOROLZROZXCS-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-hydroxy-pent-3-en-2-one 在 lithium hydroxide 作用下， 以49%的产率得到(+/-)-(3S,3aS,7aR)-3-(hydroxymethyl)-6-methyl-1,3,3a,4,7,7a-hexahydro-4-isobenzofuranone
  参考文献：
  名称：

  通过γ-羟基烯酮的Oxa-Michael / Michael环化反应合成功能化的四氢呋喃。

  摘要：

  提出了一种基于新型的顺式-γ-羟基烯酮的Oxa-Michael / Michael二聚化的高度官能化的四氢呋喃衍生物的方法。该反应以1,2-二恶英或反式-γ-羟基烯酮开始，并且通过将一个分子的反式-γ-羟基烯酮加到另一种由醇盐或氢氧化物碱催化的顺式或反式-γ-羟基烯酮分子来进行。随后将酮-烯醇的分子内迈克尔加成，得到观察到的四氢呋喃。在γ-羟基烯酮的2-位和4-位都可以取代；然而，对于4-取代的γ-羟基烯酮，由于异手性或同手性二聚化的可能性而出现选择性问题。主要产品是那些具有所有连续基团的反式产品。

  DOI：

  10.1021/jo020700h
• 作为产物：
  描述：

  间戊二烯 在 vanadia 双氧水 作用下， 以 叔丁醇 为溶剂， 生成 (E)-5-hydroxy-pent-3-en-2-one
  参考文献：
  名称：

  Lonshchakova,T.I. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 807 - 811

  摘要：

  DOI：

文献信息

• The first practical approach to optically pure cyclopropanes derived from trans γ-hydroxy enones
  作者：Francine N. Palmer、Dennis K. Taylor

  DOI：10.1039/b001973i

  日期：——

  A new approach for the synthesis of optically pure cyclopropanes from trans γ-hydroxy enones and stabilised phosphorus ylides is presented; the use of light and a triplet sensitiser leads to a dramatic increase in reaction rate and isolated yield.

  一种新的方法被提出，用于从反式γ-羟基烯酮和稳定磷叶立德合成光学纯的环丙烷；使用光和三重态敏化剂显著提高了反应速率和分离产率。
• Tandem additions of 3,4-dihydroisoquinolines to γ-hydroxy-α,β-unsaturated ketones: a green and new access to oxazolo[2,3-a]tetrahydroisoquinolines
  作者：Sheng-Han Huang、Yu-Wei Shih、Wen-Tse Huang、Deng-Hong Li、Te-Fang Yang

  DOI：10.1039/c6ra20708a

  日期：——

  Addition reaction of 3,4-dihydroisoquinolines with γ-hydroxy-α,β-unsaturated ketones furnished a variety of diastereomerically pure oxazolo[2,3-a]tetrahydro-isoquinolines, which could be purified by either recrystallization or solvent evaporation. The reaction proceeded smoothly under “green” conditions without an additive and catalyst, giving the target molecules in good to excellent yields.

  3,4-二氢异喹啉与γ-羟基-α，β-不饱和酮的加成反应提供了多种非对映体纯的恶唑并[2,3 - a ]四氢异喹啉，可以通过重结晶或溶剂蒸发法将其纯化。在没有添加剂和催化剂的“绿色”条件下，反应可顺利进行，从而使目标分子的收率良好至极佳。
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
• Low Catalyst Loading in the Cross Metathesis of Olefins with Methyl Vinyl Ketone
  作者：Christian Slugovc、Muddasar Abbas、Anita Leitgeb

  DOI：10.1055/s-0033-1338425

  日期：——

  An olefin-metathesis catalyst featuring a 1,3-bis(2,6-di-isopropylphenyl)-4,5-dihydroimidazol-2-ylidene N-heterocyclic carbene and an ester-chelating carbene ligand efficiently promoted the cross metathesis of olefins with 3-buten-2-one in the presence of copper iodide as cocatalyst. At optimized reaction conditions a 1020 times lower catalyst loading compared to the state of the art could be achieved.
• Grimaldi,J.; Bertrand,M., Bulletin de la Societe Chimique de France, 1971, p. 973 - 979
  作者：Grimaldi,J.、Bertrand,M.

  DOI：——

  日期：——