α,α-diphenyl-5-(dimethylamino)salicyl alcohol | 1044218-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: α,α-diphenyl-5-(dimethylamino)salicyl alcohol
• 英文别名: 4-(dimethylamino)-2-(hydroxydiphenylmethyl)phenol；4-(Dimethylamino)-2-(hydroxydiphenylmethyl)phenol；4-(dimethylamino)-2-[hydroxy(diphenyl)methyl]phenol
• CAS: 1044218-12-3
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: HWEDBSODXZRCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α,α-diphenyl-5-(dimethylamino)salicyl alcohol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(二甲氨基)-2-(二苯基(3-苯基丙氧基)甲基)苯酚
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c
• 作为产物：
  描述：

  methyl 5-(dimethylamino)-2-hydroxybenzoate 、 苯基锂 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到α,α-diphenyl-5-(dimethylamino)salicyl alcohol
  参考文献：
  名称：

  顺序除去具有控制波长的羰基光不稳定保护基

  摘要：

  已经开发出一组坚固且易于制造的羰基化合物的光不稳定保护基（PPG）。通过控制照射波长，可以依次去除不同的PPG。

  DOI：

  10.1021/jo8008275

文献信息

• Development of a Photolabile Carbonyl-Protecting Group Toolbox
  作者：Haishen Yang、Xin Zhang、Lei Zhou、Pengfei Wang

  DOI：10.1021/jo102429g

  日期：2011.4.1

  New salicyl alcohol derived photolabile carbonyl protecting groups have been developed, and the effect of substituents on the photochemical properties of photolabile protecting groups (PPGs) has been studied. The 3-(dimethylamino)phenyl groups at the α position prove to be important to the efficiency of the deprotection reactions, as shown in the photo reactions of the acetal 9. On the other hand,

  已经开发了新的水杨醇衍生的光不稳定的羰基保护基，并且已经研究了取代基对光不稳定的保护基（PPG）的光化学性质的影响。如在乙缩醛9的光反应中所示，在α位置的3-（二甲基氨基）苯基被证明对于脱保护反应的效率是重要的。。另一方面，将水杨醇的苯骨架扩展为萘并不能改善PPG的光化学性质。中性保护方案已推广到具有α，α-二芳基水杨醇骨架的新型PPG。因此，在不使用任何其他化学试剂的情况下，可以轻松地在140°C下将PPG安装在醛上。这些PPG在典型的水解乙缩醛的酸性条件下稳定，并与传统的羰基化合物的1,3-二恶烷/ 1,3-二恶戊环构成正交保护基。已经证明了碳水化合物分子的高效释放，其对于碳水化合物的位点特异性释放和固定化对于制备高密度微阵列可能潜在有用。借助丰富的PPG工具箱，PPG根据其紫外线吸收曲线分为三个亚组。来自不同亚组的PPG可以通过使用不同的紫外线照射波长顺序去除。对于吸收UVA（λ> 315
• A photocleavable linker for the chemoselective functionalization of biomaterials
  作者：Liz O'Donovan、Paul A. De Bank

  DOI：10.1039/c2jm35173k

  日期：——

  The functionalization of matrices with “caged” functional groups and their subsequent selective uncaging is a promising approach for generating patterns of bioactive molecules to guide cell growth or recreate in vivo microarchitectures. To date, this has been limited to caged carboxylic acids, amines and thiols, functional groups found within biological systems. We present a bifunctional caged carbonyl linker as an alternative approach for the chemoselective functionalization of biomaterials. This linker was readily coupled to collagen, employed as a model biomaterial, and underwent rapid uncaging in aqueous media upon irradiation with ultraviolet light to yield free carbonyl groups. Modified surfaces proved to be non-adhesive to cells until the chemoselective reintroduction of adhesion following incubation of uncaged carbonyls with gelatin hydrazide, with native gelatin failing to elicit a cellular response.

  使用“笼状”功能团对基质进行功能化，并随后选择性地去笼是一种有前景的方法，用于生成生物活性分子的模式，以引导细胞生长或重现体内微结构。到目前为止，这种方法仅限于笼状羧酸、胺和硫醇，这些功能团在生物系统中存在。我们提出了一种双功能笼状羰基连结剂，作为生物材料化学选择性功能化的替代方法。该连结剂可以轻松与胶原蛋白结合，胶原蛋白被用作模型生物材料，并在紫外光照射下迅速去笼，在水介质中释放出游离羰基。经过修饰的表面对细胞显示出非粘附性，直到去笼羰基与明胶肼孵育后选择性重新引入了粘附，而原生明胶未能引起细胞反应。
• Sequential Removal of Photolabile Protecting Groups for Carbonyls with Controlled Wavelength
  作者：Pengfei Wang、Yun Wang、Huayou Hu、Cierra Spencer、Xing Liang、Lurong Pan

  DOI：10.1021/jo8008275

  日期：2008.8.1

  A group of robust and easy-to-make photolabile protecting groups (PPGs) for carbonyl compounds has been developed. Sequential removal of different PPGs is achieved via control of irradiation wavelength.

  已经开发出一组坚固且易于制造的羰基化合物的光不稳定保护基（PPG）。通过控制照射波长，可以依次去除不同的PPG。
• Development of Trityl-Based Photolabile Hydroxyl Protecting Groups
  作者：Lei Zhou、Haishen Yang、Pengfei Wang

  DOI：10.1021/jo200692c

  日期：2011.8.5

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.