2,2-dimethyl-5-phenylhexan-3-one | 55830-03-0

• 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: 2,2-dimethyl-5-phenylhexan-3-one
• CAS: 55830-03-0
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: UVIHTFNCDHMOPY-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 0.1 Torr)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,2-dimethyl-5-phenylhexan-3-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 1.0h， 生成 (2SR,3SR,4RS,1'RS)-3-(1,1-dimethylethyl)-2-phenyl-4-(1-phenylethyl)-3-[(trimethylsilyl)oxy]oxetane
  参考文献：
  名称：

  1,3-Allylic Strain as a Control Element in the Paternò−Büchi Reaction of Chiral Silyl Enol Ethers:  Synthesis of Diastereomerically Pure Oxetanes Containing Four Contiguous Stereogenic Centers

  摘要：

  The facial diastereoselectivity in the Patemo-Buchi reaction of chiral silyl enol ethers and benzaldehyde was studied. The substituents (R(S), R(L)) at the stereogenic carbon atom (-C*HR(S)R(L)) attached to the beta-position of the silyl enol ether were varied in order to evaluate the influence of steric bulk and electronic effects. The combined yields for the two diastereomeric 3-(silyloxy)oxetanes a and b. range between 44% and 76%. In accordance with the 1,3-allylic strain model the facial diastereoselectivity (diastereomeric ratio (dr) = alb) was best with large(R(L) = t-Bu, SiMe(2)Ph) and polar (R(L) = OMe) substituents at the gamma-position of the silyl enol ether (dr up to >95/5). Two regioselective ring opening reactions were applied to the product oxetanes 29a, 50, and 51. They furnished diastereomerically pure diols (52, 53) and triols (31) in excellent yields.

  DOI：

  10.1021/ja963827v
• 作为产物：
  描述：

  频哪酮 、 1-氯-1-苯乙烷 在 sodium amide 作用下， 生成 2,2-dimethyl-5-phenylhexan-3-one
  参考文献：
  名称：

  Montignoul, Claude; Richard, Marie-Josee; Vigne, Christian, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1509 - 1519

  摘要：

  DOI：

文献信息

• Nickel-catalyzed Conjugate Addition of Arylboron Reagents to α,β-Unsaturated Carbonyl Compounds with the Aid of a Catalytic Amount of an Alkyne
  作者：Eiji Shirakawa、Yuichi Yasuhara、Tamio Hayashi

  DOI：10.1246/cl.2006.768

  日期：2006.7

  Alkynes in combination with a catalytic amount of a nickel complex were found to catalyze the conjugate addition of arylboron reagents to α,β-unsaturated carbonyl compounds, where use of an optical...

  发现炔烃与催化量的镍络合物结合可催化芳基硼试剂与 α,β-不饱和羰基化合物的共轭加成，其中使用光学...
• Desulfitative Pd-catalysed coupling reaction using benzenesulfonyl chlorides and enones as the coupling partners
  作者：Kedong Yuan、Rui Sang、Jean-François Soulé、Henri Doucet

  DOI：10.1039/c5cy00089k

  日期：——

  The reaction of benzenesulfonyl chlorides with enones was investigated. β-Ionone and benzalacetone in the presence of a palladium catalyst were found to afford the conjugate addition products instead of the expected Heck type products. The reaction tolerates a wide variety of substituents on the benzenesulfonyl chloride. It should be noted that no cleavage of the C–Br and C–I bonds was observed in

  研究了苯磺酰氯与烯酮的反应。发现在钯催化剂存在下，β-紫罗兰酮和苯并丙酮可提供共轭加成产物，而不是预期的Heck型产物。该反应可耐受苯磺酰氯上的各种取代基。应该指出的是，在与4-溴或4-碘-苯磺酰氯的反应过程中，未观察到C-Br和C-I键的裂解，可以进行进一步的转化。例如，使用4-溴苯磺酰氯作为中心单元，在芳基化之后连续的共轭加成允许获得取代的双（杂）芳基。
• Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
  作者：Yoshihiro Nishimoto、Takahiro Saito、Makoto Yasuda、Akio Baba

  DOI：10.1016/j.tet.2009.03.106

  日期：2009.7

  The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

  描述了烷基氯化物与InBr 3催化的烯醇硅酸酯的偶联反应，以及烷基醚与InBr 3 / Me 3 SiBr的路易斯酸催化的烯醇硅酸酯的偶联反应。在两个反应系统中，都使用了各种类型的甲硅烷基烯酸酯，以生成相应的α-烷基化的酯，酮，羧酸，酰胺，硫代酯和醛。
• Holm, Torkil, Acta Chemica Scandinavica, 1991, vol. 45, # 9, p. 925 - 929
  作者：Holm, Torkil

  DOI：——

  日期：——
• Malmberg, Hans; Nilsson, Martin; Ullenius, Christina, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 9, p. 625 - 630
  作者：Malmberg, Hans、Nilsson, Martin、Ullenius, Christina

  DOI：——

  日期：——