4-Phenyl-1-buten-3,4-diol | 19261-14-4

• 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: 4-Phenyl-1-buten-3,4-diol
• 英文别名: 1-Phenylbut-3-ene-1,2-diol
• CAS: 19261-14-4
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: WIVMOHUVHFHFLN-UHFFFAOYSA-N

物化性质

• 沸点：
  311.4±37.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Phenyl-1-buten-3,4-diol 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 对甲苯磺酸 作用下， 生成 4-Hydroxy-4-phenyl-1-buten-3-one
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157
• 作为产物：
  描述：

  (2E)-1-phenylbut-2-en-1-ol 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 四氯化碳 为溶剂， 生成 4-Phenyl-1-buten-3,4-diol
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157

文献信息

• Stereoselective Synthesis of γ-Substituted (<i>Z</i>)-Allylic Boranes via Kinetically Controlled Hydroboration of Allenes with 10-TMS-9-borabicyclo[3.3.2]decane
  作者：Jeremy Kister、Amy C. DeBaillie、Ricardo Lira、William R. Roush

  DOI：10.1021/ja905494c

  日期：2009.10.14

  Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions

  丙二烯 8 和 14a-d 与容易获得的 Soderquist 硼烷 7 的动力学控制硼氢化反应（由硼氢化物 6 原位生成）构成了合成（Z）-γ-（取代）烯丙硼烷 9 和 15a 的方便且制备性有用的方法-d。这些烯丙基硼烷与代表性醛发生高度非对映（> 或 = 90: 10）和对映选择性（通常为 89-96% ee）烯丙基硼化反应，得到顺-β-官能化的高烯丙醇。
• 3-Bromopropenyl Esters in Organic Synthesis:  Indium- and Zinc-Mediated Entries to Alk-1-ene-3,4-diols
  作者：Marco Lombardo、Stefano Morganti、Claudio Trombini

  DOI：10.1021/jo0262457

  日期：2003.2.1

  Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-1-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereoselectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.
• Enantio- and Diastereoselective Synthesis of (<i>E</i>)-1,5-<i>syn</i>-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin
  作者：Jeremy Kister、Philippe Nuhant、Ricardo Lira、Achim Sorg、William R. Roush

  DOI：10.1021/ol2003836

  日期：2011.4.1

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.
• Wiemann, Annales de Chimie (Cachan, France), 1936, vol. <11>5, p. 267,304,309
  作者：Wiemann

  DOI：——

  日期：——
• A New Protocol for the Acetoxyallylation of Aldehydes Mediated by Indium in THF
  作者：Marco Lombardo、Rugiada Girotti、Stefano Morganti、Claudio Trombini

  DOI：10.1021/ol016315g

  日期：2001.9.1

  [GRAPHICS]A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta -unsaturated aldehydes preferentially lead to the syn isomers.