2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one | 647024-59-7

• 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-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one
• 英文别名: 2-Hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one
• CAS: 647024-59-7
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: KLGHUEXNXOLESD-UHFFFAOYSA-N

物化性质

• 沸点：
  332.5±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-methyl-1-morpholin-4-yl-3-phenylprop-2-en-1-one 在 C₆H₉Cl₂N₃Pd 、 叔丁基锂 作用下， 以 四氢呋喃 、 丙酮 、 正戊烷 为溶剂， 反应 26.0h， 生成 2-hydroxy-3-methyl-4-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  The Palladium(II)-Catalyzed Nazarov Reaction

  摘要：

  [GRAPHICS]The PdCl2-catalyzed cyclization of alpha-alkoxy dienones leads to 2-hydroxycyclopentenones, whereas the Pd(OAc)(2)-catalyzed reaction leads to cross-conjugated cyclopentenones through an oxidative process.

  DOI：

  10.1021/ol036017e

文献信息

• Me₃SiCF₂Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones
  作者：Jian Chang、Cong Xu、Jie Gao、Fengyun Gao、Dongsheng Zhu、Mang Wang

  DOI：10.1021/acs.orglett.7b00611

  日期：2017.4.7

  in the domino conversion of methylvinylketones into α,α-difluorinated cyclopentanones. Initiated by 5 mol % of nBu4NBr, the multistep reaction occurred in one pot under mild conditions via the in situ formation of silyl dienol ethers, difluorocyclopropanation, thermal vinylcyclopropane–cyclopentene rearrangement, and desilylation. The process takes advantage of the multitasking capability of Me3SiCF2Br

  一种基于Me 3 SiCF 2 Br的完全自助剂策略用于甲基乙烯基酮的多米诺骨转化为α，α-二氟环戊酮。由5 mol％的n Bu 4 NBr引发，在温和的条件下，在一锅中通过甲硅烷基二烯醇醚的原位形成，二氟环丙烷化，热乙烯基环丙烷-环戊烯重排和去甲硅烷基化反应，进行了多步反应。该方法利用了Me 3 SiCF 2 Br作为二氟卡宾源，硅基转移剂和溴阴离子释放剂的多任务处理能力。
• Asymmetric Brønsted Acid-Catalyzed Nazarov Cyclization of Acyclic α-Alkoxy Dienones
  作者：Sadiya Raja、Winai Ieawsuwan、Vadim Korotkov、Magnus Rueping

  DOI：10.1002/asia.201200391

  日期：2012.10

  A Brønsted acid‐catalyzed asymmetric Nazarov cyclization of acyclic α‐alkoxy dienones has been developed. The reaction offers access to chiral cyclopentenones in a highly enantioselective manner. The reaction is complementary to our previously reported Brønsted acid‐catalyzed electrocyclization reactions, which provided differently substituted optically active cyclopentenones with a fused tetrahydropyrane

  已经开发出布朗斯台德酸催化的无环α-烷氧基二烯酮的不对称纳扎罗夫环化反应。该反应以高度对映选择性的方式提供了手性环戊烯酮的进入。该反应是我们先前报道的布朗斯台德酸催化的电环化反应的补充，该反应提供了具有稠合四氢吡喃环的不同取代的旋光性环戊烯酮，且收率高，对映选择性高。
• α-Hydroxy Cyclopentenones from α-Diketones
  作者：William A. Batson、Divakaramenon Sethumadhavan、Marcus A. Tius

  DOI：10.1021/ol050970x

  日期：2005.6.1

  [reaction: see text] Metalloenolates derived from alpha,beta-unsaturated alpha-diketones undergo cyclization to alpha-hydroxy cyclopentenones. This is apparently the first reported Nazarov reaction that takes place in the presence of base.

  [反应：见正文]衍生自α，β-不饱和α-二酮的金属烯酸酯会环化成α-羟基环戊烯酮。显然这是首次报道的在碱的存在下发生的纳扎罗夫反应。
• Carbocyclic Ring Closure of Aryl <i>C</i>-Glycosides Promoted by Fluoroboric Acid
  作者：Qiannan Zheng、Shengbiao Tang、De-Cai Xiong、Qin Li、Xin-Shan Ye

  DOI：10.1021/acs.joc.0c00784

  日期：2020.7.17

  A novel transformation from rhamnose-type C-glycosides to 2-cyclopentenones is described. With the promotion of fluoroboric acid, C-glycosides underwent ring opening and subsequent Nazarov cyclization to afford 2-cyclopentenones in good to excellent yields. The solvent and the concentration of acid are crucial to the yield of this transformation.

  描述了从鼠李糖型C-糖苷到2-环戊烯酮的新型转化。随着氟硼酸的促进，对C-糖苷进行开环和随后的纳扎罗夫环化，以良好至优异的产率提供2-环戊烯酮。溶剂和酸的浓度对这种转化的产率至关重要。
• Regioselective Synthesis of α-Fluorinated Cyclopentenones by Organocatalytic Difluorocyclopropanation and Fluorine-Directed and Fluorine-Activated Nazarov Cyclization
  作者：Kohei Fuchibe、Ryo Takayama、Takaharu Yokoyama、Junji Ichikawa

  DOI：10.1002/chem.201604578

  日期：2017.2.24

  α,β‐unsaturated ketones, underwent proton sponge‐catalyzed difluorocyclopropanation with trimethylsilyl 2,2‐difluoro‐2‐fluorosulfonylacetate in a regioselective manner, leading to 1,1‐difluoro‐2‐siloxy‐2‐vinylcyclopropanes in good yields. The cyclopropanes thus obtained were in turn subjected to fluoride‐ion‐catalyzed ring opening to afford 1‐fluorovinyl vinyl ketones (i.e., Nazarov precursors). Treatment

  由α，β-不饱和酮制得的甲硅烷基二烯醇醚经质子海绵催化的2,2-二氟-2-氟磺酰乙酸三甲基甲硅烷基以区域选择性方式生成二氟环丙烷化反应，生成1,1-二氟-2-甲硅烷氧基-2-乙烯基环丙烷丰产。依次将如此获得的环丙烷进行氟离子催化的开环反应，得到1-氟乙烯基乙烯基酮（即Nazarov前体）。与我的前体的处理3的Si + B（OTF）4 -区域选择性地促进了环化纳扎罗夫，速率和区域选择性其中被急剧由氟取代基，其因此促进了生物有为α-fluorocyclopentenone衍生物有效合成增强。