(E,SR)-5-Phenylhex-3-en-2-one | 91711-97-6

• 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: (E,SR)-5-Phenylhex-3-en-2-one
• 英文别名: (E)-(5RS)-5-phenylhex-3-en-2-one；5-phenylhex-3-en-2-one；(E)-5-phenylhex-3-en-2-one；5-Phenyl-hex-3-en-2-on
• CAS: 91711-97-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: ALFALFNFEGCXJO-CMDGGOBGSA-N

物化性质

• 沸点：
  83-84.5 °C(Press: 0.05 Torr)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,SR)-5-Phenylhex-3-en-2-one 、 tert-butyl((3,3-dimethylbut-1-en-2-yl)oxy)dimethylsilane 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-7,7-Dimethyl-4-((S)-1-phenyl-ethyl)-octane-2,6-dione
  参考文献：
  名称：

  Acyclic stereoselection. Part 34. Stereoselection in the Michael addition reaction. 4. Diastereofacial preferences in Lewis acid-mediated additions of enolsilanes to chiral enones

  摘要：

  DOI：

  10.1021/jo00352a040
• 作为产物：
  描述：

  2-苯基丙醛 、 乙酰三苯基氯化磷 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 以64%的产率得到(E,SR)-5-Phenylhex-3-en-2-one
  参考文献：
  名称：

  Highly Effective Vinylogous Mukaiyama−Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane

  摘要：

  Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) performed as an excellent acid catalyst for the vinylogous Mukaiyama-Michael reaction of alpha,beta-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted gamma-butenolide structure.

  DOI：

  10.1021/jo902641g

文献信息

• Enantio- and Regioselective Conjugate Addition of Organometallic Reagents to Linear Polyconjugated Nitroolefins
  作者：Matthieu Tissot、Alexandre Alexakis

  DOI：10.1002/chem.201300538

  日期：2013.8.19

  The copper‐catalysed conjugate addition of trialkylaluminium and dialkylzinc reagents to polyconjugated nitroolefins (nitrodiene and nitroenyne derivatives) is reported. A reversed Josiphos ligand L7 allows for the selective 1,4‐ or 1,6‐addition with high enantioselectivities.

  据报道，铜催化将三烷基铝和二烷基锌试剂共轭加成到共轭硝基烯烃（硝基二烯和亚硝基炔衍生物）中。反向的Josiphos配体L7可实现对映体选择性高的选择性1,4或1,6加成。
• Diastereofacial selectivity via aldol reactions using ethyl dithioacetate and ethyl dithiopropionate enolates
  作者：A.I. Meyers、Robert D. Walkup

  DOI：10.1016/s0040-4020(01)96754-7

  日期：1985.1

  The lithium enolate of ethyl dithioacetate reacts with α-methyl aldehydes to yield the aldol products in which the syn configuration in the positions β and γ to the thiocarbonyl of the product is favored over the anti configuration. This selectivity is solvent-dependent, and is enhanced at lower temperatures. In most cases, syn:anti product ratios obtained under these conditions varied from 57:43 to

  二硫代乙酸乙酯的烯醇锂与α-甲基醛反应生成醛醇产物，其中相对于抗构象，在产物的硫代羰基的β和γ位的顺式构象更有利。该选择性取决于溶剂，并且在较低的温度下会提高。在大多数情况下，根据α-甲基醛的结构，在这些条件下获得的顺式：反式产物比率从57:43到> 99：1不等。当使二硫代丙酸乙酯的烯醇锂与α-甲基醛反应时，在产物混合物中仅检测到四种可能的非对映异构体中的两种。
• REACTION OF ENOL ACETATE WITH ACETAL AND CARBONYL COMPOUND IN THE PRESENCE OF LEWIS ACID
  作者：Teruaki Mukaiyama、Toshio Izawa、Kazuhiko Saigo

  DOI：10.1246/cl.1974.323

  日期：1974.4.5

  It was found that, in the presence of Lewis acid such as TiCl4, AlCl3, SnCl4, ZnCl2, and BF3·O(C2H5)2, enol acetate reacts with various acetals and benzaldehyde to afford the corresponding aldol-type addition products in good yields.

  发现在路易斯酸如 TiCl4、AlCl3、SnCl4、ZnCl2 和 BF3·O(C2H5)2 的存在下，烯醇乙酸酯与各种缩醛和苯甲醛反应，以良好的收率得到相应的醇醛型加成产物.
• Synthesis of <i>E</i>-α,β-Unsaturated Ketones with Complete Stereoselectivity via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium ­Diiodide or Chromium Dichloride
  作者：José Concellón、Humberto Rodríguez-Solla、Carmen Concellón、Pamela Díaz

  DOI：10.1055/s-2006-933146

  日期：——

  E-α,β-Unsaturated ketones can be obtained with complete E-selectivity by a sequential reaction of dichloroketones with a variety of aldehydes. This transformation was promoted by SmI2, SmI2 in the presence of FeCl3 or CrCl2. The best results were obtained when CrCl2 was used as the metallating agent. A mechanism based on a successive aldol-type reaction and a β-elimination is ­proposed to explain these results.

  通过二氯酮与各种醛的连续反应，可以得到具有完全E选择性的E-α,β-不饱和酮。 SmI2、SmI2 在 FeCl3 或 CrCl2 存在下促进了这种转化。当使用CrCl2作为金属化剂时获得了最好的结果。提出了基于连续羟醛型反应和β-消除的机制来解释这些结果。
• Catalyst for asymmetric epoxidation of enones and process for producing optically active epoxide employing it
  申请人：——

  公开号：US20010051737A1

  公开（公告）日：2001-12-13

  A complex catalyst for asymmetric epoxidation of enones, which comprises: (A) an optically active binaphthol, (B) lanthanum triisopropoxide, (C) triphenylphosphine oxide, and (D) cumene hydroperoxide or tert-butyl hydroperoxide.

  一种用于不对称環氧化烯酮的复杂催化剂，包括：（A）光学活性的二萘酚，（B）三异丙氧化镧，（C）三苯基氧化膦和（D）叔丁基过氧化氢或叔丙基过氧化氢。