2-(Hydroxy-phenyl-methyl)-1-phenyl-pent-4-en-1-one | 134853-08-0

• 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: 2-(Hydroxy-phenyl-methyl)-1-phenyl-pent-4-en-1-one
• 英文别名: 2-[Hydroxy(phenyl)methyl]-1-phenylpent-4-en-1-one
• CAS: 134853-08-0
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: BXQPKEXCZQSLJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-allyl-1,3-diphenyl-1,3-propanedione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(Hydroxy-phenyl-methyl)-1-phenyl-pent-4-en-1-one
  参考文献：
  名称：

  A novel sunscreen agent having antimelanoma activity

  摘要：

  A novel series of eight dibenzoylmethane derivatives having both sunscreen and cytotoxic activity has been obtained by derivatizing commercial dibenzoyl methanes. Four human cancer cell lines (MCF 7 (breast), NCI ADR (breast expressing the multidrug resistance phenotype), NCI 460 (lung) and UACC 62 (melanoma)) were used for the cytotoxic assay. Eight among the 19 dibenzoylmethane derivatives showed cytotoxicity against these four cell lines. Absorption spectroscopies revealed that these compounds can be used as sunscreens against UV radiation.

  DOI：

  10.1016/s0014-827x(03)00195-2

文献信息

• Free radical trapping of α-keto radicals derived from α,β-epoxy ketones via photoinduced single electron transfer process
  作者：Eietsu Hasegawa、Kenyuki Ishiyama、Takaaki Horaguchi、Takahachi Shimizu

  DOI：10.1016/s0040-4039(00)78899-x

  日期：1991.4

  Irradiation of aromatic α,β-epoxy ketones in the presence of allyltributyltin afforded α-allyl-β-hydroxy ketones by a single electron transfer mechanism.

  在烯丙基三丁基锡的存在下辐照芳族α，β-环氧酮可通过单电子转移机理得到α-烯丙基-β-羟基酮。
• Photochemically and thermally induced free-radical reactions of .alpha.,.beta.-epoxy ketones with tributyltin hydride: selective C.alpha.-O bond cleavage of oxiranylmethyl radicals derived from .alpha.,.beta.-epoxy ketones
  作者：Eietsu Hasegawa、Kenyuki Ishiyama、Tomoyasu Kato、Takaaki Horaguchi、Takahachi Shimizu、Shoji Tanaka、Yoshiro Yamashita

  DOI：10.1021/jo00046a016

  日期：1992.9

  Free-radical reactions of alpha,beta-epoxy ketones with tributyltin hydride have been studied. These substances were selectively converted to beta-hydroxy ketones under both photochemical and thermal conditions. The photoreaction is initiated by hydrogen abstraction of an epoxy ketone triplet from tributyltin hydride, while azoisbutyronitrile is used as an initiator for the thermal reaction. In general, the photoreaction conditions are particularly useful for aroyl-substituted epoxy ketones while the thermal conditions are applicable to a variety of epoxy ketones. It was also found that the epoxy esters and epoxy alcohols did not undergo the ring-opening reaction under the similar conditions. Tributyltin radical attack on the carbonyl of epoxy ketones is a key process for both the photoreaction and the thermal reaction. Regioselective ring opening of the resulting oxiranylmethyl radical finally produces beta-hydroxy ketones. In order to capture the free-radical intermediates, the reaction of epoxy ketones with allyltributyltin was conducted. The isolation of alpha-allylated beta-hydroxy ketones is interpreted by the involvement of a novel 1,5-tributyltin transfer.