3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene | 25983-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene
• 英文别名: 2,6-bis(O-benzyl)benzaldehyde；2,6-bisbenzyloxybenzaldehyde；2,6-Dibenzyloxybenzaldehyde；2,6-Dibenzyloxybenzaldehyd；2,6-Bis-benzyloxybenzaldehyde；2,6-bis(phenylmethoxy)benzaldehyde
• CAS: 25983-53-3
• 化学式: C₂₁H₁₈O₃
• 分子量: 318.372
• InChiKey: HODTWSSKUTVXMG-UHFFFAOYSA-N

物化性质

• 熔点：
  77 °C
• 沸点：
  503.3±40.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene 在 chromium(VI) oxide 、 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 环己烷 、 丙酮 为溶剂， 反应 1.16h， 生成
  参考文献：
  名称：

  Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits

  摘要：

  A series of analogues of the protein kinase C (PKC) inhibitory natural product balanol which bear modified benzophenone subunits are described. The analogues were designed with the goal of uncovering structure - activity features that could be used in the development of PKC inhibitors with a reduced polar character compared to balanol itself. The results of these studies suggest that most of the benzophenone features found in the natural product are important for obtaining potent PKC inhibitory compounds. However, several modifications were found to lead to selective inhibitors of the related enzyme protein kinase A (PKA), and several specific modifications to the polar structural elements of the benzophenone were found to provide potent PKC inhibitors. In particular, it was found that replacement of the benzophenone carboxylate with bioisosteric equivalents could lead to potent analogues. Further, a tolerance for lipophilic substituents on the terminal benzophenone ring was uncovered. These results are discussed in light of recently available structural information for PKA.

  DOI：

  10.1021/jm020018f
• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 lithium aluminium tetrahydride 、 Collins oxidation agent 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.0h， 生成 3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene
  参考文献：
  名称：

  Asymmetric reduction with 5-deazaflavin. II. Synthesis of some chiral 5-deazaflavin derivatives.

  摘要：

  为了开发功能性仿生辅酶模型，我们制备了一些新型手性 5-脱氮黄素衍生物。我们合成了在 C(6)位具有手性取代基(13)和在 C(5)位具有手性三级不对称碳中心的 5-脱氮黄素衍生物（15a、b、17a、b 和 18a、b），并取得了相当令人满意的收率。为了研究由此获得的模型的效率，我们用 15a、b 对苯甲酰甲酸乙酯进行了不对称还原的初步实验，结果发现不对称诱导的程度适中或较低。

  DOI：

  10.1248/cpb.38.312

文献信息

• The flavan–isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift–alkylation sequence
  作者：Kayo Nakamura、Ken Ohmori、Keisuke Suzuki

  DOI：10.1039/c5cc01572c

  日期：——

  An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (-)-equol, a natural isoflavan with estrogenic activities, was achieved.

  据报道，基于儿茶素骨架中芳基的1,2-转移，然后进行原位烷基化，可以实现2-取代异黄酮的制备。合成了具有雌激素活性的天然异黄酮（-）-雌马酚。
• Synthesis of facially-encumbered porphyrins. An approach to light-harvesting antenna complexes
  作者：Richard W. Wagner、James Ruffing、Bradly V. Breakwell、Jonathan S. Lindsey

  DOI：10.1016/s0040-4039(00)74308-5

  日期：1991.4

  2,6-di- and 2,4,6-tri-benzyloxybenzaldehydes are converted to the respective octa- and dodeca-benzyloxy porphyrins in 9–52% yields via the two-step one-flask room-temperature porphyrin synthesis.

  通过两步式一瓶室温卟啉合成，将2，6-二和2,4,6-三苄氧基苯甲醛以9-52％的产率转化为相应的八-和十二-苄氧基卟啉。
• Water Accessibility to the Binding Cleft as a Major Switching Factor from Entropy-Driven to Enthalpy-Driven Binding of an Alkyl Group by Synthetic Receptors
  作者：Sayaka Matsumoto、Hiroya Iwamoto、Tadashi Mizutani

  DOI：10.1002/asia.200900679

  日期：2010.5.3

  drove the binding of the alkyl group with the enthalpic driving force being dominant. The binding site of the four‐pillared receptor (1) is open and accessible to water molecules, and is more hydrophilic than that of the eight‐pillared receptor (4). We propose that the alkyl chains of 1 are exposed to water to produce a room to accommodate the guest to result in enthalpy‐driven hydrophobic binding, whereas

  确定了烷基吡啶与水溶性锌卟啉受体的结合中的自由能，焓和熵的变化，以及水对结合裂隙的可及性的变化，以解释为什么疏水作用的驱动力在某些情况下是焓，而在另一些情况下是熵。卟啉锌带有四个烷基支柱，其末端增溶的聚（氧化乙烯）（POE）链的分子量为750（1），八个烷基支柱，其末端增溶的POE链的分子量为350（3），并且具有八个烷基支柱，其分子量分别为350（3）分子量750的POE（4）具有结合裂隙，其水可及性以该顺序降低，如通过咪唑/吡啶的结合选择性所揭示的。尽管所有这些卟啉表明，结合（-Δ的自由能G ^ ö）线性增加作为烷基客体的加长（-Δ ģ ö每CH 2为2.6，2.8和2.6千焦耳摩尔-1为1，分别为3和4），自由能获取的来源有很大不同。受体1与最亲水的结合位点由焓驱动力结合的烷基（4- pentylpyridine青睐通过ΔΔ过度-4-甲基吡啶ħ ö = -16.4千焦摩尔-1），而受体4与由熵驱动力最疏水的结合位点（4-
• Synthesis and Fluorescence Properties of Selectively Metallated Diporphyrins with Electron-Accepting Moieties
  作者：Toshi Nagata

  DOI：10.1246/bcsj.64.3005

  日期：1991.10

  Synthesis of selectively metallated diporphyrins with electron-accepting moieties is described. Steady-state fluorescence spectra of these compounds snowed substantial quenching of the fluorescence of the free-base porphyrin. A possible “superexchange” mechanism of long-range electron transfer is discussed.

  文中描述了带有电子受体基团的金属选择性络合二卟啉的合成方法。这些化合物的稳态荧光光谱显示，自由基卟啉的荧光显著淬灭。文章讨论了一种可能的“超交换”机制，即长程电子转移机制。
• A 2:1 Coupling Reaction of Arynes with Aldehydes via <i>o</i>-Quinone Methides:  Straightforward Synthesis of 9-Arylxanthenes
  作者：Hiroto Yoshida、Masahiko Watanabe、Hiroyuki Fukushima、Joji Ohshita、Atsutaka Kunai

  DOI：10.1021/ol048298b

  日期：2004.10.1

  [reaction: see text] A novel coupling reaction, where an aldehyde and two molar amounts of an aryne are assembled selectively, has been demonstrated to afford diverse 9-arylxanthene derivatives in one step. o-Quinone methide arising from the [2 + 2] cycloaddition of an aldehyde with an aryne was postulated as a transient intermediate.

  [反应：见正文]已证明一种新颖的偶联反应，其中醛和两个摩尔量的芳烃选择性地组装，可在一个步骤中提供多种9-芳基x吨衍生物。假定由醛与芳烃的[2 + 2]环加成反应生成的邻苯二甲酰甲基甲烷作为过渡中间体。