2-hydroxy-5-methyl-1,2-diphenyl-hex-4-en-1-one | 128720-37-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-hydroxy-5-methyl-1,2-diphenyl-hex-4-en-1-one
• 英文别名: 2-hydroxy-5-methyl-1,2-diphenylhex-4-en-1-one；1,2-Diphenyl-2-hydroxy-5-methylhex-4-en-1-on
• CAS: 128720-37-6
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: QAQTULCFTIUOBW-UHFFFAOYSA-N

物化性质

• 沸点：
  442.3±33.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  梨醇酯 、 安息香精油 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium hydride 、 二氢二苯磷苯基-4-异丙恶唑 作用下， 以 二氯甲烷 为溶剂， 以31%的产率得到2-hydroxy-5-methyl-1,2-diphenyl-hex-4-en-1-one
  参考文献：
  名称：

  Palladium-Catalyzed C-Allylation of Benzoins and an NHC-Catalyzed Three Component Coupling Derived Thereof: Compatibility of NHC- and Pd-Catalysts

  摘要：

  A large range of benzoins was successfully applied as C-nucleophiles in the palladium-catalyzed allylic alkylation with several allyl acetates, resulting in functionalized tertiary homoallylic alcohols. A number of unsymmetrical benzoins can be coupled with high levels of regio- and chemoselectivity. Finally, the challenging compatibility of free N-heterocyclic carbenes with a palladium catalyst has been utilized in a number of metal- and organocatalyzed three-component coupling reactions.

  DOI：

  10.1021/ol801644f

文献信息

• Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents
  作者：Yutaka Nishigaichi、Takayuki Orimi、Akio Takuwa

  DOI：10.1016/j.jorganchem.2009.08.011

  日期：2009.11

  Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the reaction selectivity and the negative free energy change for the electron transfer process.

  可以将三氟硼酸烯丙酯和苄基三氟硼酸酯通过光诱导的单电子转移途径以可接受的收率用于羰基化合物的光反应，以提供相应的醇加合物。从反应选择性和电子转移过程的负自由能变化中证实了该结果。
• Highly Regio- and Stereoselective Allylation of α-Diketones via the Fluorosilicate Route
  作者：Rainer Gewald、Mitsuo Kira、Hideki Sakurai

  DOI：10.1055/s-1996-4151

  日期：1996.1

  Allylation of enolizable α-diketones with allyltrifluorosilanes in the presence of triethylamine gave the corresponding tertiary homoallyl alcohols in good yield in a highly regio- and stereospecific manner. The reaction proceeds as diallylation with allyltrifluorosilanes yielding the 1,2-diols with high diastereoselectivity. The more sterically demanding crotyl- and prenyltrifluorosilanes lead exclusively to monoallylated products with the allyl group being added γ-regioselectively. In addition, highly diastereoselective crotylation was observed in the formation of the monoallylated α-hydroxy ketones. Asymmetric α-diketones were generally allylated at the less enolized ketone group except when both diketone and allylsilane were sterically hindered.

  在三乙胺存在下，使用烯丙基三氟硅烷对可烯醇化的α-二酮进行烯丙基化，得到了相应的三级同烯丙醇，产率良好，并且具有高度的区域选择性和立体选择性。该反应以双烯丙基化进行，使用烯丙基三氟硅烷生成具有高二元选择性的1,2-二醇。更具空间位阻的烯丙基-和预烯丙基三氟硅烷则专门生成单烯丙基化产物，烯丙基团以γ-区域选择性加成。此外，在形成单烯丙基化的α-羟基酮时观察到了高度的二元选择性烯丙基化。当二酮和烯丙基硅烷都受到空间位阻时，通常对不太烯醇化的酮基进行烯丙基化。
• Reaction of .pi.-allylnickel bromide complexes with ketones and aldehydes. Synthesis of .alpha.-methylene-.gamma.-butyrolactones
  作者：L. S. Hegedus、S. D. Wagner、E. L. Waterman、K. Siirala-Hansen

  DOI：10.1021/jo00893a012

  日期：1975.3
• First examples of hypervalent enhancement of photoallylation by allylsilicon compounds via photoinduced electron transfer
  作者：Yutaka Nishigaichi、Akira Suzuki、Takahiro Saito、Akio Takuwa

  DOI：10.1016/j.tetlet.2005.05.124

  日期：2005.8

  Hypervalency (pentacoordination) of silicon atom enhanced photoallylation of 1,2-diketones with allylsilicon reagents, while normal tetracoordinated ones could not. This reaction seems to proceed via photoinduced electron transfer from the silicon reagent to the photoexcited ketone judged from its reactivity and selectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• Takuwa, Akio; Nishigaichi, Yutaka; Yamashita, Koichi, Chemistry Letters, 1990, # 4, p. 639 - 642
  作者：Takuwa, Akio、Nishigaichi, Yutaka、Yamashita, Koichi、Iwamoto, Hidetoshi

  DOI：——

  日期：——