n-butyl trans-cinnamyl ketone | 98859-39-3

• 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: n-butyl trans-cinnamyl ketone
• 英文别名: (E)-1-phenyloct-1-en-4-one
• CAS: 98859-39-3
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: WRTAMWLGEWSMBO-JXMROGBWSA-N

物化性质

• 沸点：
  331.7±21.0 °C(Predicted)
• 密度：
  0.962±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：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine 在 正丁基锂 、 ammonium molybdate 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 n-butyl trans-cinnamyl ketone
  参考文献：
  名称：

  2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine-1,1-dioxide 的烷基化，一类新的酰基阴离子等价物，可替代二噻吩

  摘要：

  (2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine-1,1-dioxide 已被发现在区域选择性去质子化时与多种亲电子试剂反应，例如各种卤化物和醛。这该方法利用砜基团形成新的碳-碳键，同时充当掩蔽的羰基。随后的砜水解为许多有用的合成中间体提供了一种简便的方法。这种方法可以提供一种有用的替代二噻烷基团的方法。

  DOI：

  10.3987/com-06-s(w)56

文献信息

• Palladium Catalyzed Coupling Reaction of Acylchromate Complexes and Allylic Bromides
  作者：Hidehiro Sakurai、Katsuhiko Tanabe、Koichi Narasaka

  DOI：10.1246/cl.1999.309

  日期：1999.4

  cross-coupling reaction between acylchromate complexes and allylic bromides takes place under CO atmosphere in the presence of a catalytic amount of Pd(PPh3)4 to afford the corresponding allylic ketones in good yield. The same reaction also proceeds by adding RNC under argon atmosphere in place of CO atmosphere. Thus, the acylchromate complex works as a good acyl donor for Pd catalyzed acylation reaction.

  在催化量的 Pd(PPh3)4 存在下，在 CO 气氛下，酰基铬酸盐配合物和烯丙基溴之间发生交叉偶联反应，以良好的收率提供相应的烯丙基酮。通过在氩气气氛下添加 RNC 代替 CO 气氛，也可以进行相同的反应。因此，酰基铬酸盐络合物可作为 Pd 催化酰化反应的良好酰基供体。
• Carbonylative Cross‐Coupling Reaction of Allylic Alcohols and Organoalanes with 1 atm CO Enabled by Nickel Catalysis
  作者：Chenglong Wang、Xianqing Wu、Haiyan Li、Jingping Qu、Yifeng Chen

  DOI：10.1002/anie.202210484

  日期：2022.9.19

  The direct chemoselective carbonylative cross-coupling reaction of allylic alcohols and organoalanes with 1 atm CO via nickel catalysis has been developed to access the β,γ-unsaturated ketones with broad scope. The use of organoalanes as both the coupling components and the activators for the alcohol functionalization was found to be both crucial and advantageous as the method does not require any

  已经开发了通过镍催化烯丙醇和有机烷烃与 1 atm CO 的直接化学选择性羰基化交叉偶联反应来获得具有广泛范围的 β,γ-不饱和酮。由于该方法不需要任何外部活化剂，因此发现使用有机丙烷作为偶联组分和醇官能化的活化剂既是关键又是有利的。
• Phosphinecarbonylnitrosylacylcobaltate complexes as acyl transfer reagents. Acylation of allylic halides, conjugated enones, and quinones
  作者：Louis S. Hegedus、Robert J. Perry

  DOI：10.1021/jo00224a061

  日期：1985.11
• Selective Functionalization of a Variety of Hydrocarbon C(sp³)–H Bonds Initiated by Cp*W(NO)(CH₂CMe₃)(η³-CH₂CHCHPh)
  作者：Russell J. Wakeham、Rhett A. Baillie、Brian O. Patrick、Peter Legzdins、Devon C. Rosenfeld

  DOI：10.1021/acs.organomet.6b00739

  日期：2017.1.9

  Cp*W(NO)(CH2CMe3)(eta(3)-CH2CHCHPh) (1) effects C(sp(3))-H activations of methane, ethane, propane, and n-butane exclusively at their terminal carbons and forms the corresponding Cp*W(NO)(alkyl)(eta(3)-CH2CHCHPh) complexes. It also activates (n-Bu)(2)O, 1-chloropropane, and Me4Si in a similar manner. Exposure of the Cp*W(NO)(alkyl)(eta(3)-CH2CHCHPh) complexes to carbon monoxide results in initial 1,1-CO insertion into the newly formed tungsten alkyl bonds and formation of the corresponding eta(1)-aryl complexes, some of which can be isolated. Additional functionalization of the C -H activation products occurs upon exposure to CO under more forcing conditions. Such treatment produces eta(2)-bound unsaturated-ketone complexes resulting from CO insertion into the W-alkyl sigma bonds followed by cross-coupling of the eta(1)-aryl and the eta(3)-allyl ligands and coordination of CO at the resulting vacant coordination site at tungsten. The unsaturated ketones can be released from the metal's coordination spheres either by photolysis of the complexes in MeCN or by further exposure of them to CO. All new compounds have been characterized by conventional spectroscopic and analytical methods, and. the solid-state molecular structures of six of them have been established by single-crystal X-ray crystallographic analyses.
• Alkylation of 2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine-1,1-dioxide, a New Class of Acyl Anion Equivalents as an Alternative to Dithianes
  作者：Robert K. Boeckman、Susan M. Hanson、Jeremy A. Cody

  DOI：10.3987/com-06-s(w)56

  日期：——

  ,3]oxathiine-1,1-dioxide has been found to react with several electrophiles, such as various halides and aldehydes, upon regioselective deprotonation. This method utilizes the sulfone group to form new carbon-carbon bonds while serving as a masked carbonyl. Subsequent hydrolysis of the sulfone provides a facile approach toward many useful synthetic intermediates. This methodology could provide a useful

  (2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine-1,1-dioxide 已被发现在区域选择性去质子化时与多种亲电子试剂反应，例如各种卤化物和醛。这该方法利用砜基团形成新的碳-碳键，同时充当掩蔽的羰基。随后的砜水解为许多有用的合成中间体提供了一种简便的方法。这种方法可以提供一种有用的替代二噻烷基团的方法。