(E)-1-hydroxy-1-phenylhex-4-en-3-one | 651738-86-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-1-hydroxy-1-phenylhex-4-en-3-one
• 英文别名: 6-hydroxy-6-phenyl-2-hexen-4-one
• CAS: 651738-86-2；259227-39-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: VWVNHNNRZMUMFB-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  (E)-1-hydroxy-1-phenylhex-4-en-3-one 在 palladium dichloride disodium hydrogenphosphate 、 氧气 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 以86%的产率得到6-甲基-2-苯基-2,3-二氢吡喃-4-酮
  参考文献：
  名称：

  Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones

  摘要：

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.

  DOI：

  10.1021/ol0361296
• 作为产物：
  描述：

  (E)-5-phenyl-3-(prop-1-en-1-yl)-4,5-dihydroisoxazole 在 samarium diiodide 、 氧气 、 硼酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.83h， 生成 (E)-1-hydroxy-1-phenylhex-4-en-3-one
  参考文献：
  名称：

  通过共轭腈氧化物环加成和oxa-Michael环化反应生成四氢吡喃-4-酮的短而灵活的途径：（+/-）-双ponspongin A的简明非对映选择性全合成。

  摘要：

  开发了一种短而灵活的[3 + 2 + 1]合成策略，用于合成取代的四氢吡喃-4-酮，其特征在于，α，β-不饱和腈和烯烃的[3 + 2]-环加成反应和oxa-Michael环化反应6-endo-trig时尚。该合成策略的效率通过8个步骤的简明全合成（+/-）-双倍体皂苷A（20.2％的产率）得到了进一步证明。

  DOI：

  10.1039/c2cc37772a

文献信息

• Lanthanide(III) Promoted Aldol Condensation of Enones and Aldehydes¹
  作者：Bor-Cherng Hong、Sheng-Fei Chin

  DOI：10.1080/00397919708003356

  日期：1997.4

  Abstract The first lanthanide (III) mediated α′-alkylation of MVK with aldehydes is described. This methodology allows the efficient preparation of a number of synthetically important hydroxyenones.

  摘要描述了第一个镧系元素 (III) 介导的 MVK 与醛的 α'-烷基化。这种方法允许有效地制备许多合成上重要的羟基烯酮。
• Experiments Directed Towards the Synthesis of Anthracyclinones. XXXIV Hetero-Diels - Alder Reactions Using Chiral Boron and Titanium Reagents
  作者：Mark D. Bercich、Richard C. Cambie、Peter S. Rutledge

  DOI：10.1071/ch98181

  日期：——

  Reactions between benzaldehyde or o-anisaldehyde and a series of silyloxy dienes catalysed by the chiral acyl- oxyborane (CAB) complex (4) give high yields of enantioselective products from a Mukaiyama aldol rather than a hetero-Diels–Alder reaction. Attempts to effect a similar catalytic reaction with anthraquinone aldehydes were unsuccessful but use of 2 equiv. of the CAB complex (1) followed by cyclization promotes a formal hetero- Diels–Alder reaction between the aldehyde (7) and the diene (12) to give the dihydropyrone (24) in 45% yield and with a 79% e.e. in favour of the 2'R enantiomer. Hetero-Diels–Alder reactions between the aldehyde (7) and the diene (12) using the chiral titanium complexes Ti[(R)-BINOL]Cl 2 , Ti[(R,R)-TADDOL]Cl 2 and Ti[(R)-BINOL] 2 have been investigated. The first two complexes promote the reaction at −30 and −78° respectively but with low induced enantioselectivities.

  苯甲醛或邻甲氧基苯甲醛与一系列硅烷氧基二烯通过手性酰氧硼烷（CAB）配合物（4）催化反应，产生高收率的对向异构体产物，而不是杂环Diels-Alder反应。尝试使用蒽醌醛进行类似的催化反应失败，但使用2当量的CAB配合物（1）随后进行环化反应，促进了醛（7）和二烯（12）之间的形式杂环Diels-Alder反应，产生二氢吡喃（24），收率为45％，对2'R对映体有79％的对映选择性。使用手性钛配合物Ti [(R)-BINOL] Cl2，Ti [(R,R)-TADDOL] Cl2和Ti [(R)-BINOL] 2进行了醛（7）和二烯（12）之间的杂环Diels-Alder反应的研究。前两种配合物分别在-30℃和-78℃促进反应，但对映选择性较低。
• A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxidescycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A
  作者：Hongliang Yao、Jingyun Ren、Rongbiao Tong

  DOI：10.1039/c2cc37772a

  日期：——

  flexible [3+2+1] synthetic strategy was developed for the synthesis of substituted tetrahydropyran-4-ones, featuring [3+2]-cycloaddition of alpha,beta-unsaturated nitrile oxides and alkenes and oxa-Michael cyclization in a 6-endo-trig fashion. The efficiency of this synthetic strategy was further demonstrated by the concise total synthesis of (+/-)-diospongin A in 8 steps with 20.2% yield.

  开发了一种短而灵活的[3 + 2 + 1]合成策略，用于合成取代的四氢吡喃-4-酮，其特征在于，α，β-不饱和腈和烯烃的[3 + 2]-环加成反应和oxa-Michael环化反应6-endo-trig时尚。该合成策略的效率通过8个步骤的简明全合成（+/-）-双倍体皂苷A（20.2％的产率）得到了进一步证明。
• Oxidative Cyclization of β-Hydroxyenones with Palladium(II):  A Novel Entry to 2,3-Dihydro-4<i>H</i>-pyran-4-ones
  作者：Maud Reiter、Sandrine Ropp、Véronique Gouverneur

  DOI：10.1021/ol0361296

  日期：2004.1.1

  A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.