4-(1-hydroxy-1-phenyl-3-butenyl)benzaldehyde | 130925-79-0

• 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-(1-hydroxy-1-phenyl-3-butenyl)benzaldehyde
• 英文别名: 4-(1-Hydroxy-1-phenylbut-3-enyl)benzaldehyde
• CAS: 130925-79-0
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: XBCYVBKHWXRMJU-UHFFFAOYSA-N

物化性质

• 沸点：
  426.5±33.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-{4-[Hydroxy-(1,2,3,4,5-pentamethyl-cyclopenta-2,4-dienyl)-methyl]-phenyl}-1-phenyl-but-3-en-1-ol 在 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 4-(1-hydroxy-1-phenyl-3-butenyl)benzaldehyde
  参考文献：
  名称：

  Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to aromatic aldehydes and carbon–carbon bond cleavage of the adducts affording the parent aldehydes

  摘要：

  Treatment of aromatic aldehyde with lithium pentamethylcyclopentadienide provided the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to an acid or due to heating. The combination of the two reactions can represent a protection of aromatic aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.094

文献信息

• Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon–carbon bond cleavage of the adducts yielding the parent carbonyl compounds
  作者：Minoru Uemura、Kazunari Yagi、Masayuki Iwasaki、Kenichi Nomura、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.tet.2006.01.097

  日期：2006.4

  dienide (C5Me5Li, Cp*Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp*Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns

  五甲基环戊二烯化锂（C 5 Me 5 Li，Cp * Li）与芳族醛反应以优异的产率提供相应的甲醇。甲醇在暴露于酸中或加热后会返回为母体醛和五甲基环戊二烯。氯二甲基铝对于实现Cp * Li向脂肪族醛的亲核加成反应至关重要。衍生自脂族醛的甲醇在催化量的2,3-二氯-5,6-二氰基苯并醌（DDQ）的作用下返回母体醛和五甲基环戊二烯。Cp *基团的可逆加成/消除可表示对醛的保护。还公开了碳-碳键裂解的机理细节。
• Regioreversed Allylation in Lewis Acid-mediated and Photochemical Addition Reactions of Unsymmetric α-Diketones with Allylic Stannanes
  作者：Akio Takuwa、Yutaka Nishigaichi、Koichi Yamashita、Hidetoshi Iwamoto

  DOI：10.1246/cl.1990.1761

  日期：1990.9

  In the photochemical reaction of allyl- and benzyltrimethylstannanes with unsymmetric α-diketones (PhCOCOR), the allylic group was introduced to the benzoyl carbon in high or excellent selectivity, whereas the acyl carbon was allylated either exclusively or predominantly under BF3-mediated reaction.

  在烯丙基和苄基三甲基锡与不对称α-二酮（PhCOCOR）的光化学反应中，烯丙基基团以高或优异选择性引入到苯酰碳上，而在BF3催化的反应中，酰基碳则被烯丙基化，要么是专一性地，要么是以主要方式。