3-hydroxy-2-methylene-3-phenylpropanal | 54827-29-1

• 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-hydroxy-2-methylene-3-phenylpropanal
• 英文别名: 3-phenyl-3-hydroxy-2-methylenepropanal；2-[hydroxy(phenyl)methyl]acrylaldehyde；2-[Hydroxy(phenyl)methyl]prop-2-enal
• CAS: 54827-29-1
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: XKRAXXJUQGKUNA-UHFFFAOYSA-N

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：
  0.1
• 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-hydroxy-2-methylene-3-phenylpropanal 在 N-chlorosuccinimide-dimethylsulfide complex 作用下， 生成 (Z)-2-(chloromethyl)-3-phenylacrylaldehyde
  参考文献：
  名称：

  Depazay,J.-C.; Le Merrer,Y., Tetrahedron Letters, 1974, p. 2751 - 2754

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Diethoxymethyl-1-phenyl-prop-2-en-1-ol 在 硫酸 作用下， 生成 3-hydroxy-2-methylene-3-phenylpropanal
  参考文献：
  名称：

  Depazay,J.-C.; Le Merrer,Y., Tetrahedron Letters, 1974, p. 2751 - 2754

  摘要：

  DOI：

文献信息

• Lithium perchlorate-accelerated Baylis-Hillman reactions
  作者：Mikako Kawamura、Shū Kobayashi

  DOI：10.1016/s0040-4039(98)02705-1

  日期：1999.2

  The coupling of α,β-unsaturated carbonyl compounds with aldehydes (the Baylis-Hillman reaction) was accelerated in the presence of a catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) and lithium perchlorate in ether. A preliminary kinetic study revealed that the relative rate of the reaction using LiClO4 in ether was 8.0×102 times faster than that of the reaction without LiClO4.

  在乙醚中催化量的1,4-二氮杂双环[2,2,2]辛烷（DABCO）和高氯酸锂的存在下，促进了α，β-不饱和羰基化合物与醛的偶联（Baylis-Hillman反应） 。初步动力学研究表明，使用的LiClO反应的相对速率4在乙醚中为8.0×10 2比没有的LiClO反应更快倍4。
• An Improved Protocol for the Morita‐Baylis‐Hillman Reaction Allows Unprecedented Broad Synthetic Scope
  作者：Nilton S. Camilo、Hugo Santos、Lucas A. Zeoly、Fábio S. Fernandes、Manoel T. Rodrigues、Thiago S. Silva、Samia R. Lima、José Cláudio Serafim、Aline S. B. de Oliveira、Arthur G. Carpanez、Giovanni W. Amarante、Fernando Coelho

  DOI：10.1002/ejoc.202101448

  日期：2022.3.7

  By the combination of DABCO and acetic acid under solvent-free conditions, the Morita-Baylis-Hillman reaction rate of both activated and non-activated aldehydes increased significantly. The disclosed procedure is operationally simple and is compatible with a wide array of both nucleophilic and electrophilic reaction partners.

  通过在无溶剂条件下将 DABCO 和乙酸结合，活化和未活化醛的 Morita-Baylis-Hillman 反应速率均显着提高。所公开的程序操作简单并且与多种亲核和亲电反应伙伴相容。
• α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions
  作者：Gangababu Marri、Frédéric Justaud、Saibal Das、René Grée

  DOI：10.1002/ejoc.201801343

  日期：2019.1.10

  A short approach toward new acrolein‐type derivatives, functionalized in position 2 is described. It involves, as the key step, a smooth transformation of acylsilanes into aldehydes by irradiation in water‐organic solvent mixtures. The functionalized enals obtained by this new route appear as versatile building blocks for the preparation of natural products and/or bioactive compounds.

  描述了一种新的丙烯醛类衍生物的简短方法，该衍生物在位置2进行了功能化。作为关键步骤，它涉及通过在水-有机溶剂混合物中进行辐照将酰基硅烷平稳地转化为醛。通过这种新途径获得的功能化的烯醛似乎是用于制备天然产物和/或生物活性化合物的通用结构单元。
• Strunz, George M.; Bethell, Richard; Sampson, Glen, Canadian Journal of Chemistry, 1995, vol. 73, # 10, p. 1666 - 1674
  作者：Strunz, George M.、Bethell, Richard、Sampson, Glen、White, Peter

  DOI：——

  日期：——
• Highly Stereoselective Coupling Reaction of Acrolein or Vinyl Ketone with Aldehydes
  作者：Shigeki Uehira、Zhenfu Han、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/ol990934w

  日期：1999.11.1

  [GRAPHICS]Treatment of acrolein with a TiCL4-n-Bu(4)Nl mixed reagent in the presence of 2 equiv of aldehydes provided 4-hydroxy-1,3-dioxane derivatives in good yields with high stereoselectivities. The use of vinyl ketones instead of acrolein afforded aldo-type adducts with high syn selectivities.