cassiferaldehyde | 1160707-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: cassiferaldehyde
• 英文别名: (E)-3-(3-hydroxy-2-methoxyphenyl)prop-2-enal
• CAS: 1160707-53-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: LNYOLAZJJYTRSO-HWKANZROSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  357.3±32.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cassiferaldehyde 、 2-羟基苯乙酮 在 N-[(1R,2R)-2-氨基环己基]-N'-[3,5-双(三氟甲基)苯基]硫脲 、 Jorgensen-Hayashi catalyst 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以54.545%的产率得到
  参考文献：
  名称：

  2-羟基苯乙酮与烯醛之间的有机催化不对称迈克尔-半缩醛化反应：一条通往手性β，γ-二取代γ-丁内酯的途径

  摘要：

  公开了使用2-羟基苯乙酮的第一个高对映选择性有机催化反应，即2-羟基苯乙酮与烯醛的迈克尔-半缩醛化反应。发现伯胺和仲胺催化剂的组合是该方法的最佳选择。该反应的产物以高对映体和非对映体选择性获得，并转化为多种生物学上重要的γ-丁内酯。

  DOI：

  10.1021/acs.joc.7b00363
• 作为产物：
  描述：

  3-羟基-2-甲氧苯甲醛 、 甲酰甲撑基三苯基磷 以 甲苯 为溶剂， 反应 1.0h， 以34%的产率得到cassiferaldehyde
  参考文献：
  名称：

  Syntheses and X-Ray Crystal Structures of Cassiferaldehyde and Analogs

  摘要：

  Cassiferaldehyde, a recently discovered naturally occurring tyrosinase inhibitor, and six of its analogs, in which the aldehyde group has been replaced by various other functionalities, have been synthesized by a short and simple sequence starting from 2,3-dihydroxybenzaldehyde. Single-crystal x-ray structures of cassiferaldehyde as well as its methyl ketone, nitrile, and carboxylic acid analogs are reported.

  DOI：

  10.1080/00397911.2010.523921

文献信息

• Organocatalytic Asymmetric Michael-Hemiacetalization Reaction Between 2-Hydroxyacetophenones and Enals: A Route to Chiral β,γ-Disubstituted γ-Butyrolactones
  作者：Megha Balha、Buddhadeb Mondal、Subas Chandra Sahoo、Subhas Chandra Pan

  DOI：10.1021/acs.joc.7b00363

  日期：2017.6.16

  The first highly enantioselective organocatalytic reaction employing 2-hydroxyacetophenones is disclosed, namely Michael-hemiacetalization reaction of 2-hydroxyacetophenones with enals. The combination of a primary amine and a secondary amine catalyst was found to be the best choice for this methodology. The products of this reaction were obtained in high enantio- and diastereoselectivities and were

  公开了使用2-羟基苯乙酮的第一个高对映选择性有机催化反应，即2-羟基苯乙酮与烯醛的迈克尔-半缩醛化反应。发现伯胺和仲胺催化剂的组合是该方法的最佳选择。该反应的产物以高对映体和非对映体选择性获得，并转化为多种生物学上重要的γ-丁内酯。
• Syntheses and X-Ray Crystal Structures of Cassiferaldehyde and Analogs
  作者：Jessica L. Levasseur、Dasan M. Thamattoor

  DOI：10.1080/00397911.2010.523921

  日期：2012.1.15

  Cassiferaldehyde, a recently discovered naturally occurring tyrosinase inhibitor, and six of its analogs, in which the aldehyde group has been replaced by various other functionalities, have been synthesized by a short and simple sequence starting from 2,3-dihydroxybenzaldehyde. Single-crystal x-ray structures of cassiferaldehyde as well as its methyl ketone, nitrile, and carboxylic acid analogs are reported.