2,2-diphenyl-1,3-dioxolane-4-carbaldehyde | 907203-97-8

• 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: 2,2-diphenyl-1,3-dioxolane-4-carbaldehyde
• CAS: 907203-97-8
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: JGBKLYXCAFVOTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-diphenyl-1,3-dioxolane-4-carbaldehyde 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 trans-1-benzyl-2-(2,2-diphenyl-1,3-dioxolan-4-yl)-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Synthesis and NMDA-receptor affinity of 4-oxo-dexoxadrol derivatives

  摘要：

  A synthesis of novel dexoxadrol analogues is described, which allows modifications of the piperidine substructure. The key step of the synthesis is a hetero Diels-Alder reaction of the imine 12 with Danishefsky's diene 6. After separation of the diastereomeric piperidones 14a and 14b, the relative configuration of the unlike configured piperidone 15b was determined by X-ray crystal structure analysis. In receptor binding studies the like configured secondary amine 15a (racemate) showed considerable affinity toward the phencyclidine binding site of the NMDA receptor (K-i = 470 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.020
• 作为产物：
  描述：

  (2,2-diphenyl-1,3-dioxolan-4-yl)methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到2,2-diphenyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and NMDA-receptor affinity of 4-oxo-dexoxadrol derivatives

  摘要：

  A synthesis of novel dexoxadrol analogues is described, which allows modifications of the piperidine substructure. The key step of the synthesis is a hetero Diels-Alder reaction of the imine 12 with Danishefsky's diene 6. After separation of the diastereomeric piperidones 14a and 14b, the relative configuration of the unlike configured piperidone 15b was determined by X-ray crystal structure analysis. In receptor binding studies the like configured secondary amine 15a (racemate) showed considerable affinity toward the phencyclidine binding site of the NMDA receptor (K-i = 470 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.020

文献信息

• Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates
  作者：P. Veeraraghavan Ramachandran、Daniel Nicponski、Bomi Kim

  DOI：10.1021/ol400381q

  日期：2013.3.15

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.