3-(1-hydroxy-1-benzyl)-2-methyl-2-cyclopenten-1-one | 74600-36-5

• 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: 3-(1-hydroxy-1-benzyl)-2-methyl-2-cyclopenten-1-one
• 英文别名: 3-(hydroxy(phenyl)methyl)-2-methylcyclopent-2-en-1-one；3-[Hydroxy(phenyl)methyl]-2-methylcyclopent-2-en-1-one
• CAS: 74600-36-5
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: UHCMMVGMDBKKOY-UHFFFAOYSA-N

物化性质

• 沸点：
  378.9±31.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-hydroxy-1-benzyl)-2-methyl-2-cyclopenten-1-one 、 原乙酸三乙酯 在 丙酸 作用下， 反应 2.0h， 以88%的产率得到{1-Methyl-2-oxo-5-[1-phenyl-meth-(E)-ylidene]-cyclopentyl}-acetic acid ethyl ester
  参考文献：
  名称：

  An efficient and versatile synthesis of β-alkylidene-α,α-disubstituted cyclopentanones

  摘要：

  DOI：

  10.1016/s0040-4039(00)74556-4
• 作为产物：
  描述：

  苯甲醛 在 盐酸 作用下， 反应 14.5h， 生成 3-(1-hydroxy-1-benzyl)-2-methyl-2-cyclopenten-1-one
  参考文献：
  名称：

  An efficient and versatile synthesis of β-alkylidene-α,α-disubstituted cyclopentanones

  摘要：

  DOI：

  10.1016/s0040-4039(00)74556-4

文献信息

• Photoredox‐Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C−H Bond Activation
  作者：Kai Guo、Zhongchao Zhang、Anding Li、Yuanhe Li、Jun Huang、Zhen Yang

  DOI：10.1002/anie.202000743

  日期：2020.7.6

  Photoredox‐catalyzed isomerization of γ‐carbonyl‐substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C−H bond activation. This catalytic redox‐neutral process resulted in the synthesis of 1,4‐dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density

  γ-羰基取代的烯丙醇的光氧化还原催化异构化为其相应的羰基化合物是首次通过CH键进行活化。这种催化的氧化还原中性过程导致了1,4-二羰基化合物的合成。值得注意的是，带有四取代烯烃的烯丙基醇也可以转化成它们相应的羰基化合物。密度泛函理论计算表明，烯丙醇的γ位上的羰基有利于形成具有较高垂直电子亲和力的相应烯丙基醇自由基，这有助于完成光氧化还原催化循环。
• Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics
  作者：Paul Knochel、C. Janakiram Rao

  DOI：10.1016/s0040-4020(01)80504-4

  日期：1993.1

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.