3-(2,4-二氯苯基)-2-丙烯-1-醇 | 1504-59-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 中文名称: 3-(2,4-二氯苯基)-2-丙烯-1-醇
• 英文名称: 3-(2.4-Dichlor-phenyl)-prop-2-en-1-ol
• 英文别名: 2,4-Dichlor-cinnamylalkohol；3-(2,4-Dichlorophenyl)prop-2-en-1-ol
• CAS: 1504-59-2
• 化学式: C₉H₈Cl₂O
• 分子量: 203.068
• InChiKey: UDPMVWJTVXNMOD-UHFFFAOYSA-N

物化性质

• 沸点：
  339.3±32.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2,4-二氯苯基)-2-丙烯-1-醇 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 20.59h， 生成 Methyl 4-[3-(2,4-dichlorophenyl)propylsulfanyl]-3-oxobutanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  methyl 2,4-dichlorocinnamate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(2,4-二氯苯基)-2-丙烯-1-醇
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds
  作者：Santhosh Rao、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.orglett.6b03836

  日期：2017.2.17

  A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rearrangement occurs between in situ generated donor–acceptor gold–carbenes and cinnamyl alcohols via tandem oxonium ylide formation. The desired rearranged product has been accomplished selectively over more conventional O–H insertion, cyclopropanation, cycloaddition, and C–H functionalization products

  已经开发了金催化的[2,3]-σ重排反应。分子间重排发生在原位产生的供体-受体金-卡宾与肉桂醇之间，通过串联叶立德形成。在较温和的露天条件下，所需的重排产物已选择性地比常规的OH插入，环丙烷化，环加成和CHH功能化产物选择性地完成。通过合成一类新的可用于构建复杂分子靶标的底物，说明了这项工作的范围。
• Boron‐Catalyzed C−C Functionalization of Allyl Alcohols
  作者：Santhosh Rao、Raja Kapanaiah、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201801389

  日期：2019.3.15

  talyzed C−C bond functionalization of arylallyl alcohols using donor‐acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal‐free transformation presents

  本文介绍了使用供体-受体碳烯的三（五氟苯基）硼烷催化的芳基烯丙醇的C-C键功能化。发现烯丙基羟基通过邻近基团的参与来协助产物形成，从而提供了对机械理解的线索。该方法也可用于使烯丙醇同化为烯丙基醇。总的来说，这种无金属的转变为碳-碳键的断裂和形成提供了一种新颖的分离策略。
• (4, 5, 6, 7-Tetrahydro-1-H-Indol-7-Yl) Acetic Acid Derivatives for Treatment of Alzheimer's Disease
  申请人：Bettati Michela

  公开号：US20070232678A1

  公开（公告）日：2007-10-04

  Compounds of formula I: are disclosed. The compounds are useful in treating or preventing diseases associated with deposition of Aβ in the brain.

  公式I的化合物已被披露。这些化合物可用于治疗或预防与Aβ在大脑中沉积相关的疾病。
• Substituted Piperazines as CB1 Antagonists
  申请人：Gilbert Eric J.

  公开号：US20100029607A1

  公开（公告）日：2010-02-04

  Compounds of Formula (I): or pharmaceutically acceptable salts, solvates, or esters thereof, are useful in treating diseases or conditions mediated by CB 1 receptors, such as metabolic syndrome and obesity, neuroinflammatory disorders, cognitive disorders and psychosis, addiction (e.g., smoking cessation), gastrointestinal disorders, and cardiovascular conditions.

  式(I)的化合物，或其药学上可接受的盐、溶剂合物或酯类，可用于治疗由CB1受体介导的疾病或症状，例如代谢综合征和肥胖症、神经炎性疾病、认知障碍和精神病、成瘾（例如戒烟）、胃肠疾病和心血管病症。
• Design, Synthesis, and Biological Activity of Novel Laccase Inhibitors as Fungicides against Rice Blast
  作者：Tengda Sun、Xiaoyu Jin、Xiaoming Zhang、Xingxing Lu、Changkai Wang、Jialin Cui、Huan Xu、Xinling Yang、Xili Liu、Li Zhang、Yun Ling

  DOI：10.1021/acs.jafc.2c05144

  日期：2022.11.16

  Laccase is a potential target for novel agricultural fungicide discovery. PMDD-5Y was the first agent reported with high activity against laccase to control phytopathogenic fungi. Thirty-two novel agents containing cinnamaldehyde thiosemicarbazide were synthesized with PMDD-5Y as the lead compound, with most of the target compounds exhibiting excellent activity in vitro. Compound a2 (EC50 = 9.71 μg/mL)

  漆酶是发现新型农业杀菌剂的潜在目标。PMDD-5Y是第一个报道的对漆酶具有高活性以控制植物病原真菌的试剂。以PMDD-5Y为先导化合物，合成了32种含肉桂醛氨基硫脲的新型药物，大多数目标化合物在体外表现出优异的活性。化合物a2 (EC 50 = 9.71 μg/mL)比商业杀菌剂异丙硫醇 (EC 50 = 18.62 μg/ mL) 表现出更强的抗稻瘟病菌效力。a2对水稻稻瘟病菌的疗效和保护作用均优于PMDD-5Y. 扫描电镜表明a2可引起菌丝体生长萎缩和畸形。此外，a2 (IC 50 = 0.18 mmol/L) 对漆酶的活性高于PMDD-5Y (IC 50 = 0.33 mmol/L) 和半胱氨酸 (IC 50 = 0.30 mmol/L)。分子对接分析揭示了这些化合物与漆酶之间相互作用的性质。本研究确定了一种新型漆酶抑制剂a2作为候选杀菌剂，用于控制农业中的稻瘟病。