4-[羟基(二苯基)甲基]苯甲醛 | 220176-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 4-[羟基(二苯基)甲基]苯甲醛
• 英文名称: 4-[(hydroxy)(diphenyl)methyl]benzaldehyde
• 英文别名: 4-(Hydroxydiphenylmethyl)benzaldehyde；4-[hydroxy(diphenyl)methyl]benzaldehyde
• CAS: 220176-13-6
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: SMVFLFVQDXKQHR-UHFFFAOYSA-N

物化性质

• 沸点：
  474.4±33.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  4-[羟基(二苯基)甲基]苯甲醛 在 gallium(III) triflate 、 异丙醇 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以84%的产率得到4-benzhydrylbenzaldehyde
  参考文献：
  名称：

  直接还原苯甲醇的高效Ga（OTf）3 /异丙醇催化体系

  摘要：

  这项研究旨在报告使用异丙醇作为还原剂的镓催化的首次直接还原苄醇。反应通过原位生成的苄基异丙醚的镓催化剂辅助氢化物转移而进行。该方法仅产生副产物水和丙酮，因此为二芳基甲烷和三芳基甲烷的合成提供了一种原子经济且环保的方法，而二芳基甲烷和三芳基甲烷是各种生物活性化合物和功能材料中的重要子结构。

  DOI：

  10.1002/adsc.201801135
• 作为产物：
  描述：

  4-苯甲酰基苯甲醛 在 正丁基锂 、 三氯乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 4-[羟基(二苯基)甲基]苯甲醛
  参考文献：
  名称：

  Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to aromatic aldehydes and carbon–carbon bond cleavage of the adducts affording the parent aldehydes

  摘要：

  Treatment of aromatic aldehyde with lithium pentamethylcyclopentadienide provided the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to an acid or due to heating. The combination of the two reactions can represent a protection of aromatic aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.094

文献信息

• Reactions of Difunctional Electrophiles with Functionalized Aryllithium Compounds: Remarkable Chemoselectivity by Flash Chemistry
  作者：Aiichiro Nagaki、Keita Imai、Satoshi Ishiuchi、Jun-ichi Yoshida

  DOI：10.1002/anie.201410717

  日期：2015.2.2

  Flash chemistry using flow microreactors enables highly chemoselective reactions of difunctional electrophiles with functionalized aryllithium compounds by virtue of extremely fast micromixing. The approach serves as a powerful method for protecting‐group‐free synthesis using organolithium compounds and opens a new possibility in the synthesis of polyfunctional organic molecules.

  使用流动微反应器的闪速化学反应可通过非常快速的微混合实现双官能亲电试剂与官能化芳基锂化合物的高度化学选择性反应。该方法是使用有机锂化合物进行无保护基团合成的有力方法，为多官能有机分子的合成开辟了新的可能性。
• Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon–carbon bond cleavage of the adducts yielding the parent carbonyl compounds
  作者：Minoru Uemura、Kazunari Yagi、Masayuki Iwasaki、Kenichi Nomura、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.tet.2006.01.097

  日期：2006.4

  dienide (C5Me5Li, Cp*Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp*Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns

  五甲基环戊二烯化锂（C 5 Me 5 Li，Cp * Li）与芳族醛反应以优异的产率提供相应的甲醇。甲醇在暴露于酸中或加热后会返回为母体醛和五甲基环戊二烯。氯二甲基铝对于实现Cp * Li向脂肪族醛的亲核加成反应至关重要。衍生自脂族醛的甲醇在催化量的2,3-二氯-5,6-二氰基苯并醌（DDQ）的作用下返回母体醛和五甲基环戊二烯。Cp *基团的可逆加成/消除可表示对醛的保护。还公开了碳-碳键裂解的机理细节。
• An Efficient Photo-SET-Induced Cleavage of Dithiane−Carbonyl Adducts and Its Relevance to the Development of Photoremovable Protecting Groups for Ketones and Aldehydes
  作者：William A. McHale、Andrei G. Kutateladze

  DOI：10.1021/jo981697y

  日期：1998.12.1

  Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical, which is assisted by the anion-radical of benzophenone. This mechanism is confirmed by a Hammett plot study of the cleavage in the dithiane adducts of substituted aromatic aldehydes and a deuterium kinetic isotope effect study. Ab initio computations at UHF/6-31G* and MP2/6-31G* levels of theory in conjunction with self-consistent reaction field (self-consistent isodensity-polarized continuum model), to account for the solvent effect, also support the experimental findings. The reaction is most efficient for protection of aromatic aldehydes and ketones and aliphatic ketones, and is a novel method for protecting carbonyl functionalities with a photoremovable group.
• TELOMERASE INHIBITORS AND METHODS OF THEIR USE
  申请人：Geron Corporation

  公开号：EP1109796A1

  公开（公告）日：2001-06-27
• US6518268B1
  申请人：——

  公开号：US6518268B1

  公开（公告）日：2003-02-11