2′-benzyloxycinnamaldehyde | 208118-59-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 2′-benzyloxycinnamaldehyde
• 英文别名: 3-[2-(Benzyloxy)phenyl]prop-2-enal；3-(2-phenylmethoxyphenyl)prop-2-enal
• CAS: 208118-59-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: GLTHLHKKJJVKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2′-benzyloxycinnamaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 sodium chlorite 、 potassium dihydrogenphosphate 、 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 caesium carbonate 、 对甲苯磺酸 、 异丁烯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 41.0h， 生成 (R)-4-phenylchroman-2-one
  参考文献：
  名称：

  钯/手性胺共催化α，β-不饱和醛的对映选择性β-芳基化

  摘要：

  钯和一种简单的手性胺可用作助催化剂，将芳基硼酸对映选择性共轭加成到α，β-不饱和醛上（参见方案）。（R）-（-）-姜黄烯和4-芳基-2-酮的短总合成证明了这种共催化反应的合成效用。

  DOI：

  10.1002/anie.201208634
• 作为产物：
  描述：

  Methyl 2-benzoxycinnamate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 2′-benzyloxycinnamaldehyde
  参考文献：
  名称：

  Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors

  摘要：

  A series of 2-hydroxycinnamaldehyde derivatives was synthesized for examing a structure-activity relationship for inhibition of angiogenesis. The anti-angiogenic effects of 2'-substituted cinnamaldehdes and related analogs were determined in a chick embryo chorioallantoic membrane assay system. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10008-7

文献信息

• From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange
  作者：Taichi Saito、Yuka Shimizu、Yusuke Araki、Yoshino Ohgami、Yu Kitazawa、Yoshinori Nishii

  DOI：10.1002/ejoc.202101213

  日期：2022.1.11

  Transformation of cyclopropylcarbinols 7 to 1-arylnaphthalenes 9 established a central-to-axial chirality-exchange method in two steps: i) BF3-mediated ring-opening cyclization of D-A cyclopropylcarbinols 7 (97 to >99 % ee) to afford aryldihydronaphthalenes 8, which bear ortho-R substituents on the benzene ring; ii) dehydrogenation of the obtained aryldihydronaphthalenes 8 by using DDQ furnished the

  环丙基甲醇 7 向 1-芳基萘 9 的转化分两步建立了中心轴手性交换方法：i) BF 3介导的 DA 环丙基甲醇 7（97 至 >99% ee）的开环环化得到芳基二氢萘 8 ,在苯环上带有邻位-R 取代基；ii) 通过使用 DDQ 对获得的芳基二氢萘 8 进行脱氢，为轴向手性芳基萘 9 提供 90% 至 >99% ee。
• Evaluation of cinnamaldehyde derivatives as potential protective agents against oxidative-stress induced myotube atrophy using chemical, biological and computational analysis
  作者：Prachi Gupta、Nirmaljeet Kaur、Vinod Kumar、Amit Gupta、Sanjeev Gupta、Anita Dua、Elisha Injeti、Ashwani Mittal

  DOI：10.1016/j.bioorg.2023.106661

  日期：2023.10

  mediators of atrophy that influences various cell signaling molecules. The goal of this study is to identify potential antioxidant agents that could be used to treat atrophy. In this study in vitro and in situ screening of different cinnamaldehyde (CNA) derivatives for their antioxidant effects was done along with computational analysis to understand the relationship between their chemical structure and biological

  骨骼肌萎缩是一种代谢性疾病，与发病率、死亡率增加和生活质量差相关，目前尚无 FDA 批准的药物。氧化应激是影响各种细胞信号分子的萎缩的关键介质之一。这项研究的目的是确定可用于治疗萎缩的潜在抗氧化剂。在这项研究中，对不同肉桂醛（CNA）衍生物的抗氧化作用进行了体外和原位筛选，并进行了计算分析，以了解其化学结构和生物活性之间的关系。 数据显示，2-羟基肉桂醛（2HCNA）在生理pH下比其他CNA类似物效果更好，而4-氟-2-甲氧基肉桂醛（4FoCNA）在酸性条件下表现出最大的抗氧化活性。然而，这些衍生物（2HCNA 和 4FoCNA）被发现在生理和病理生理条件下对培养的肌管（成熟肌纤维）有毒。使用活 C2C12 细胞进行的免疫荧光、明场显微镜和生化研究表明，与其他 CNA 类似物（即2-甲氧基肉桂醛 (2MeCNA) 和 2-苄氧基肉桂醛 (2BzCNA)）预孵育不仅可以维持肌管的正常形态，还可以保护它们免受H2O2
• Rhodanine-based PRL-3 inhibitors blocked the migration and invasion of metastatic cancer cells
  作者：Garam Min、Su-Kyung Lee、Hye-Nan Kim、Young-Min Han、Rhan-Hee Lee、Dae Gwin Jeong、Dong Cho Han、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2013.04.092

  日期：2013.7

  PRL-3, phosphatase of regenerating liver-3, plays a role in cancer progression through its involvement in invasion, migration, metastasis, and angiogenesis. We synthesized rhodanine derivatives, CG-707 and BR-1, which inhibited PRL-3 enzymatic activity with IC50 values of 0.8 mu M and 1.1 mu M, respectively. CG-707 and BR-1 strongly inhibited the migration and invasion of PRL-3 overexpressing colon cancer cells without exhibiting cytotoxicity. The specificity of the inhibitors on PRL-3 phosphatase activity was confirmed by the phosphorylation recovery of known PRL-3 substrates such as ezrin and cytokeratin 8. The compounds selectively inhibited PRL-3 in comparison with other phosphatases, and CG-707 regulated epithelial-to-mesenchymal transition (EMT) marker proteins. The results of the present study reveal that rhodanine is a specific PRL-3 inhibitor and a good lead molecule for obtaining a selective PRL-3 inhibitor. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors
  作者：Byoung-Mog Kwon、Seung-Ho Lee、Young-Kwon Cho、Song-Hae Bok、Seung-Ho So、Mi-Ran Youn、Soo-Ik Chang

  DOI：10.1016/s0960-894x(97)10008-7

  日期：1997.10

  A series of 2-hydroxycinnamaldehyde derivatives was synthesized for examing a structure-activity relationship for inhibition of angiogenesis. The anti-angiogenic effects of 2'-substituted cinnamaldehdes and related analogs were determined in a chick embryo chorioallantoic membrane assay system. (C) 1997 Elsevier Science Ltd.
• Palladium/Chiral Amine Co-catalyzed Enantioselective β-Arylation of α,β-Unsaturated Aldehydes
  作者：Ismail Ibrahem、Guangning Ma、Samson Afewerki、Armando Córdova

  DOI：10.1002/anie.201208634

  日期：2013.1.14

  Palladium and a simple chiral amine are used as co‐catalysts for the enantioselective conjugate addition of aryl boronic acids to α,β‐unsaturated aldehydes (see scheme). The synthetic utility of this co‐catalyzed reaction was demonstrated in the short total syntheses of (R)‐(−)‐curcumene and 4‐aryl‐2‐ones.

  钯和一种简单的手性胺可用作助催化剂，将芳基硼酸对映选择性共轭加成到α，β-不饱和醛上（参见方案）。（R）-（-）-姜黄烯和4-芳基-2-酮的短总合成证明了这种共催化反应的合成效用。