3,5-dichlorobenzylideneacetone | 1344833-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,5-dichlorobenzylideneacetone
• 英文别名: 4-(3,5-dichlorophenyl)but-3-en-2-one
• CAS: 1344833-39-1
• 化学式: C₁₀H₈Cl₂O
• 分子量: 215.079
• InChiKey: HUFNZQXJULCVSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-dichlorobenzylideneacetone 在 C₄₄H₅₃AlN₂O₂ 、 频那醇硼烷 作用下， 以 甲苯 为溶剂， 以93 %的产率得到
  参考文献：
  名称：

  氢化铝催化化学选择性Luche型还原α,β-不饱和酮

  摘要：

  合成了一种新型、简单、环保、无毒的铝催化剂，用于化学选择性还原α,β-不饱和酮。以优异的产率、温和的条件和低催化剂负载量获得了多种酮。此外，这种前所未有的方法可以立体选择性地还原天然酮。

  DOI：

  10.1039/d3dt03987k
• 作为产物：
  描述：

  3,5-二氯苯甲醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 3,5-dichlorobenzylideneacetone
  参考文献：
  名称：

  Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

  摘要：

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.039

文献信息

• Asymmetric Epoxidation of Enones by Peptide-Based Catalyst: A Strategy Inverting Juliá–Colonna Stereoselectivity
  作者：Kazuaki Kudo、Kengo Akagawa、Tomoaki Hirata

  DOI：10.1055/s-0035-1560597

  日期：——

  A resin-supported peptide catalyst with an N-terminal primary amino group was developed for asymmetric epoxidation of enones through iminium activation. The peptide has N-terminal l -3-(1-pyrenyl)alanine, a non-natural amino acid with a bulky side chain, which is connected to l -proline and then to 310-helical ( l -Leu- l -Leu-Aib)2 (Aib: 2-aminoisobutyric acid). This peptide successfully catalyzed

  开发了一种带有 N 端伯氨基的树脂负载肽催化剂，用于通过亚胺活化对烯酮进行不对称环氧化。该肽具有 N 端 l -3-(1-芘基)丙氨酸，一种具有庞大侧链的非天然氨基酸，连接到 l -脯氨酸，然后连接到 310-螺旋 ( l -Leu- l -Leu -Aib)2（Aib：2-氨基异丁酸）。该肽成功地催化了芳基上带有吸电子基团的 β-芳基取代的烯酮的不对称环氧化反应。本肽催化剂的特点是对映选择性的意义与Julia-Colonna反应相反，低聚-l-Leu催化烯酮环氧化，而两种肽催化剂均由l-氨基酸组成。
• 一种新型有机铝氢化合物的制备及其催化的不饱和醇化合物的制备方法
  申请人：北京理工大学

  公开号：CN117384199A

  公开（公告）日：2024-01-12

  本发明公开一种新型铝氢化合物的制备及其催化的不饱和醇化合物的制备方法。其制备方法如下：首先将1‑苯基‑1,3,丁二酮和2,6‑二异丙基苯胺缩合制成配体，然后将其与0.5当量的三氢化铝三甲胺反应生成新型铝氢合物。随后使用该种铝氢化合物作为催化剂催化不饱和酮类化合物与硼氢化合物进行反应并水解得到相应的不饱和醇类化合物。本发明制备方法简单，合成的铝氢化合物在不饱和酮的硼氢化反应中有着显著的效果，催化剂仅适用5％，反应速度快产率高，解决了不饱和醇化合物的制备方法中使用的催化剂价格昂贵、需要高压氢气等问题，符合绿色化学的概念。
• Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells
  作者：Wei Zhang、Radhia Benmohamed、Anthony C. Arvanites、Richard I. Morimoto、Robert J. Ferrante、Donald R. Kirsch、Richard B. Silverman

  DOI：10.1016/j.bmc.2011.11.039

  日期：2012.1

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.
• Chemoselective Luche-type reduction of α,β-unsaturated ketones by aluminium hydride catalysis
  作者：Ben Yan、Xiaoli Ma、Ziyuan Pang、Zhi Yang

  DOI：10.1039/d3dt03987k

  日期：2024.2.27

  A novel, simple, eco-friendly, non-toxic aluminium catalyst was synthesised for the chemoselective reduction of α,β-unsaturated ketones. A wide range of ketones were achieved with excellent yields, mild conditions, and low catalyst loading. Furthermore, this unprecedented method allowed for the stereoselective reduction of natural ketones.

  合成了一种新型、简单、环保、无毒的铝催化剂，用于化学选择性还原α,β-不饱和酮。以优异的产率、温和的条件和低催化剂负载量获得了多种酮。此外，这种前所未有的方法可以立体选择性地还原天然酮。