cis-1-Phenyl-1-hepten-3-one | 19184-21-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cis-1-Phenyl-1-hepten-3-one
• 英文别名: (Z)-1-phenylhept-1-en-3-one；(1Z)-1-phenylhept-1-en-3-one
• CAS: 19184-21-5
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: FXQWBEDPJCDXQM-KHPPLWFESA-N

物化性质

• 沸点：
  308.6±11.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-oxohexyl-phosphonic acid bis(2,2,2-trifluoroethyl)ester 、 苯甲醛 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以98%的产率得到
  参考文献：
  名称：

  Z- and E-selective Horner–Wadsworth–Emmons reactions

  摘要：

  In the present work, we determined and evaluated the stereochemical outcome of the Horner-Wadsworth-Emmons (HWE) reaction of 2-oxoalkylphosphonates with different ester functions (bis(2,2,2-trifluoroethyl), 2,2,2-trifluoroethyl methyl, dimethyl) and side chains (aliphatic, aromatic) with three different aldehydes (benzaldehyde, THP- and PPB-protected Corey aldehydes) under two reaction conditions. The trans protocol is generally used in the E-selective HWE reactions, while cis protocol promotes the Z-selectivity.[GRAPHICS].

  DOI：

  10.1080/00397911.2017.1319487

文献信息

• Triazole-Gold-Promoted, Effective Synthesis of Enones from Propargylic Esters and Alcohols: A Catalyst Offering Chemoselectivity, Acidity and Ligand Economy
  作者：Dawei Wang、Yanwei Zhang、Alexandria Harris、Lekh Nath S. Gautam、Yunfeng Chen、Xiaodong Shi

  DOI：10.1002/adsc.201100314

  日期：2011.10

  (TA-Au) were revealed as the effective catalysts in promoting propargylic ester rearrangement and sequential allene hydration, giving the enones with excellent yields (up to 97% yields, 0.2% loading). The catalysts could also catalyze the more challenging Meyer–Schuster rearrangement (0.5% loading, up to 98% yields). The reported reaction confirmed TA-Au as a chemoselective catalyst in promoting alkyne activation

  揭示了空气，湿气和热稳定的1,2,3-三唑配位的金（I）配合物（TA-Au）作为促进炔丙基酯重排和顺序烯化水合的有效催化剂，使烯酮具有优异的收率（最高可达产率为97％，负载为0.2％）。催化剂还可以催化更具挑战性的Meyer-Schuster重排（0.5％的负载量，最高98％的产率）。报道的反应证实TA-Au是一种化学选择性催化剂，可高效促​​进炔烃活化并改善配体经济性。
• Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of tetrabutylammonium perrhenate (VII) and p-toluenesulfonic acid
  作者：Koichi Narasaka、Hiroyuki Kusama、Yujiro Hayashi

  DOI：10.1016/s0040-4020(01)88874-8

  日期：1992.1

  Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while, β,γ-unsaturated ketones are obtained as main products by the reaction

  通过使用催化量的高丁基酸四丁铵和对甲苯磺酸水合物，使烯丙醇的烯丙基重排和/或脱水反应顺利进行。在室温下用催化剂处理炔丙醇可得到重排产物α，β-不饱和羰基化合物，而β，γ-不饱和酮是通过在1，2-二氯乙烷中回流反应得到的主要产物。还描述了该催化体系在某些合成中间体的制备中的应用。
• Contemporaneous Dual Catalysis by Coupling Highly Transient Nucleophilic and Electrophilic Intermediates Generated in Situ
  作者：Barry M. Trost、Xinjun Luan

  DOI：10.1021/ja110501v

  日期：2011.2.16

  contemporaneous dual catalysis, that selectively couples two highly reactive catalytic intermediates while overcoming competing trapping by stoichiometric reactive species also present in the reaction. The reaction proceeds via the convergence of a vanadium-catalyzed propargylic rearrangement and a palladium-catalyzed allylic alkylation. It generates a variety of α-allylated α,β-unsaturated ketones, which are

  我们在此报告了一种新的过程，我们称之为同期双催化，它选择性地偶联两种高活性催化中间体，同时克服反应中也存在的化学计量活性物质的竞争性捕获。该反应通过钒催化的炔丙基重排和钯催化的烯丙基烷基化的收敛进行。它会生成多种 α-烯丙基化的 α,β-不饱和酮，这些酮不容易通过其他方式获得。值得注意的是，这种双重催化是通过使用低催化剂负载量（1.0 mol % [Pd]，1.5 mol % [V]）实现的，并提供了良好至极好的收率（高达 98%）的所需产物。
• Triazole acetyl gold(III) catalyzed Meyer–Schuster rearrangement of propargyl alcohols
  作者：Yongchun Yang、Yanan Shen、Xiaoli Wang、Yao Zhang、Dawei Wang、Xiaodong Shi

  DOI：10.1016/j.tetlet.2016.04.043

  日期：2016.5

  A new type triazole acetyl gold(III) was prepared and found to be an effective catalyst in Meyer–Schuster rearrangement of propargyl alcohols. The reactions proceeded well under much milder conditions to afford enones bearing a wide range of functional groups, thereby opening a new avenue for gold(III) catalysis. In addition, TriaAuCl2 catalyst was also effective on promotion of a-haloenones synthesis

  制备了一种新型的三唑乙酰金（III），发现它是炔丙醇Meyer-Schuster重排的有效催化剂。反应在温和得多的条件下进行得很好，从而得到带有多种官能团的烯酮，从而为金（III）催化开辟了一条新途径。另外，TriaAuCl 2催化剂对促进α-卤代烯酮的合成也有效。
• Application of Organocerium Reagents for the Efficient Conversion of<i>Z</i>-α,β-Unsaturated Weinreb Amides to<i>Z</i>-α,β-Unsaturated Ketones
  作者：Satoshi Kojima、Tsugihiko Hidaka、Atsushi Yamakawa

  DOI：10.1246/cl.2005.470

  日期：2005.4

  The reactions of Z-rich unsaturated Weinreb amides with organolithium and organocerium reagents were examined. Taking in consideration both the extent of geometry retention and cleanness of the reaction, organocerium reagents were more effective for the conversion to Z-α,β-unsaturated ketones.

  研究了富含 Z 的不饱和 Weinreb 酰胺与有机锂和有机铈试剂的反应。考虑到几何形状的保留程度和反应的清洁度，有机铈试剂在转化为 Z-α，β-不饱和酮方面更为有效。