tert-butyl 3-(2-(3-hydroxybut-1-ynyl)phenyl)propanoate | 934601-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: tert-butyl 3-(2-(3-hydroxybut-1-ynyl)phenyl)propanoate
• 英文别名: Tert-butyl 3-[2-(3-hydroxybut-1-ynyl)phenyl]propanoate
• CAS: 934601-94-2
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: VKCIGSFKHOBBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  tert-butyl 3-(2-(3-hydroxybut-1-ynyl)phenyl)propanoate 在 草酰氯 、 二甲基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-(3-oxobut-1-ynyl)phenyl)propanoic acid
  参考文献：
  名称：

  Preparation of Strained Axially Chiral (1,5)Naphthalenophanes by Photo-dehydro-Diels−Alder Reaction

  摘要：

  The preparation of 10 (1,5)naphthalenophanes (10a-j) by photo-dehydro-Diels-Alder (PDDA) reaction is described. Owing to hindered rotation around the biaryl axis, compounds 10 are axially chiral and the separation of enantiomers by chiral HPLC was demonstrated in three cases (10a,b,e). The absolute configuration of the isolated enantiomers could be unambiguously determined by comparison of calculated and measured circular dichroism (CD) spectra. Furthermore, we analyzed ring strain phenomena of (1,5)naphthalenophanes 10. Depending on the length of the linker units, one can distinguish three classes of naphthalenophanes. Compounds 10a-c are highly strained (E-STR = 7-31 kcal/mol), and the strain is caused by small bond angles in the linker unit and deformation of the naphthalene moiety. Another type of strain is observed if the linker unit becomes relatively long (10g,h) originating from transannular interactions and is comparable with the well-known strain of medium sized rings. The naphthalenophanes 10d-f with a linker length of 10-14 atoms are only marginally strained. To clearly discriminate the different sources of strain, we defined two geometrical parameters (average central dihedral angle delta(C) and naphthalene thickness D-N) and demonstrated that they are well-suited to indicate naphthalene deformation of our naphthalenophanes 10 as well as of ten model naphthalenophanes (I-X) with different linker lengths and linking positions.

  DOI：

  10.1021/ja109118m
• 作为产物：
  描述：

  3-(2-碘苯基)丙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 生成 tert-butyl 3-(2-(3-hydroxybut-1-ynyl)phenyl)propanoate
  参考文献：
  名称：

  光-脱氢-狄尔斯-阿尔德 (PDDA) 反应 - 一种制备联芳基化合物的有效方法

  摘要：

  光化学引发的脱氢-狄尔斯-阿尔德 (PDDA) 反应是制备联芳基化合物的一种有效且通用的方法。闭环可以发生在分子间和分子内，从制备的角度来看，分子内变体的生产效率更高。可以使用多种接头将充当发色团的ynone部分与另一个乙炔基团连接起来，从而实现大的结构多功能性。此处还将讨论影响 PDDA 反应位点选择性的原理。

  DOI：

  10.1055/s-2006-958949