(E)-2-(1,3-diphenylallyl)cyclohexanone | 1141378-30-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(1,3-diphenylallyl)cyclohexanone
• 英文别名: 2-[(2E)-1,3-diphenyl-2-propen-1-yl]cyclohexanone；2-[(E)-1,3-diphenylprop-2-enyl]cyclohexan-1-one
• CAS: 1141378-30-4
• 化学式: C₂₁H₂₂O
• 分子量: 290.405
• InChiKey: OZBZFLZAMNTQCF-FOCLMDBBSA-N

物化性质

• 沸点：
  433.2±14.0 °C(predicted)
• 密度：
  1.086±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (E)-2-(1,3-diphenylallyl)cyclohexanone 在 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 potassium carbonate 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 生成 methyl 2-(2-oxocyclohexyl)-2-phenylacetate
  参考文献：
  名称：

  Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

  摘要：

  C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

  DOI：

  10.1021/ol5000988
• 作为产物：
  描述：

  环己酮 、 (E)-3-ethoxy-1, 3-diphenylprop-1-ene 在 四氢吡咯 、 1,1'-双(二苯基膦)二茂铁 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以99%的产率得到(E)-2-(1,3-diphenylallyl)cyclohexanone
  参考文献：
  名称：

  Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

  摘要：

  C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

  DOI：

  10.1021/ol5000988

文献信息

• Copper-Catalyzed Dehydrogenative Cross-Coupling Reaction between Allylic CH Bonds and α-CH Bonds of Ketones or Aldehydes
  作者：Xing-Fen Huang、Muhammad Salman、Zhi-Zhen Huang

  DOI：10.1002/chem.201402114

  日期：2014.5.26

  A dehydrogenative cross‐coupling reaction between allylic CH bonds and the α‐CH bond of ketones or aldehydes was developed using Cu(OTf)2 as a catalyst and DDQ as an oxidant. This synthetic approach to γ,δ‐unsaturated ketones and aldehydes has the advantages of broad scope for both ketones and aldehydes as reactants, mild reaction conditions, good yields and atom economy. A plausible mechanism using

  以Cu（OTf）2为催化剂，DDQ为氧化剂，开发了烯丙基CH键与酮或醛的α- CH键之间的脱氢交叉偶联反应。这种合成γ，δ-不饱和酮和醛的方法具有以下优点：酮和醛均作为反应物，反应条件温和，收率高，原子经济。还提出了使用Cu（OTf）2作为路易斯酸催化剂的合理机理（DDQ = 2,3-二氯-5,6-二氰基-1,4-苯醌； Tf =三氟甲磺酸盐）。
• Oxovanadium(V)‐Catalyzed Deoxygenative Coupling Reaction of Alcohols with Trimethylsilyl Enol Ethers in the Presence of MS3A
  作者：Takanari Matsutani、Takashi Sakuramoto、Kento Okabayashi、Mamoru Tobisu、Toshiyuki Moriuchi

  DOI：10.1002/ejoc.202201410

  日期：——

  coupling reaction of allyl alcohols with trimethylsilyl enol ethers was performed by using a commercially available oxovanadium(V) catalyst, providing γ,δ-unsaturated carbonyl compounds in one-step. This catalytic system could be applied to a gram-scale catalytic synthesis of the γ,δ-unsaturated carbonyl compound and the deoxygenative coupling reaction of benzyl alcohols with trimethylsilyl enol ethers

  烯丙醇与三甲基甲硅烷基烯醇醚的脱氧偶联反应是通过使用市售的氧钒 (V) 催化剂进行的，一步得到γ，δ-不饱和羰基化合物。该催化体系可应用于γ , δ-不饱和羰基化合物的克级催化合成以及苯甲醇与三甲基甲硅烷基烯醇醚的脱氧偶联反应。
• Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups
  作者：Xiaohong Huo、Mao Quan、Guoqiang Yang、Xiaohu Zhao、Delong Liu、Yangang Liu、Wanbin Zhang

  DOI：10.1021/ol5000988

  日期：2014.3.21

  C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).