5-phenyl-6-hepten-3-one | 80359-92-8

• 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: 5-phenyl-6-hepten-3-one
• 英文别名: 5-phenylhept-6-en-3-one
• CAS: 80359-92-8
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: YAJJZKZHKPOINF-UHFFFAOYSA-N

物化性质

• 沸点：
  275.5±9.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  丙酸桂酯 在 丙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 为溶剂， 反应 26.5h， 生成 5-phenyl-6-hepten-3-one
  参考文献：
  名称：

  Ketal Claisen rearrangements of simple aliphatic ketals

  摘要：

  DOI：

  10.1021/jo00170a002

文献信息

• Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement
  作者：G. William Daub、James P. Edwards、Carol R. Okada、Jana Westran Allen、Claudia Tata Maxey、Matthew S. Wells、Alexandra S. Goldstein、Michael J. Dibley、Clarence J. Wang、Daniel P. Ostercamp、Steven Chung、Paula Shanklin Cunningham、Martin A. Berliner

  DOI：10.1021/jo9614250

  日期：1997.4.1

  The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to

  三取代的烯丙基醇的原酸酯克莱森重排表现出显着水平的非对映选择性。在E烯丙基醇中，在椅子状过渡状态下会形成1,3-二轴相互作用，从而导致反异构体，使反应的Syn选择性达到3-5：1。在Z烯丙基醇中，1,3-二轴相互作用相互作用以过渡状态发展，导致顺式异构体，产生6-15对1的反式：顺式选择性。顺式异构体的相对立体化学是通过霉菌毒素葡萄孢菌素的合成独立确定的。
• Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling
  作者：Faben A. Cruz、Zhiwei Chen、Sarah I. Kurtoic、Vy M. Dong

  DOI：10.1039/c6cc02522f

  日期：——

  Herein, we describe a regioselective Rh-catalyzed decarboxylative cross-coupling of [small beta]-keto acids and alkynes to access branched [gamma],[small delta]-unsaturated ketones. Rh-hydride catalysis enables the isomerization of an alkyne to generate a metal-allyl...

  在本文中，我们描述了小β-酮酸和炔的区域选择性Rh催化的脱羧交叉偶联以进入支链的γ，β-不饱和酮。氢化铑催化能够使炔烃异构化以生成金属烯丙基...
• Stereoselective acid-catalyzed Claisen rearrangements
  作者：G. William Daub、Paula L. Shanklin、Claudia Tata

  DOI：10.1021/jo00367a041

  日期：1986.8
• Ruthenium-Catalyzed Decarboxylative Allylation of Nonstabilized Ketone Enolates
  作者：Erin C. Burger、Jon A. Tunge

  DOI：10.1021/ol049097a

  日期：2004.7.1

  Bipyridyl(pentamethylcyclopentadienyl)ruthenium chloride is an efficient catalyst for the formal [3,3] rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl ruthenium intermediates, which are selectively attacked at the more substituted allyl terminus by freely diffusing enolates. Decarboxylation of beta-ketocarboxylates allows generation of enolates under extremely mild conditions.
• Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines
  作者：Jian-Ping Chen、Qian Peng、Bai-Lin Lei、Xue-Long Hou、Yun-Dong Wu

  DOI：10.1021/ja2039503

  日期：2011.9.14

  alpha-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations.