1-(2-chlorophenyl)-4-phenylbutane-1,4-dione | 1014980-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-chlorophenyl)-4-phenylbutane-1,4-dione
• 英文别名: 1-(2-Chlorophenyl)-4-phenylbutane-1,4-dione
• CAS: 1014980-12-1
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: OBSDOSIWAQJJGX-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±25.0 °C(predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-4-phenylbutane-1,4-dione 在 trans-{RuCl₂[(S)-BINAP][(S)-DAIPEN]} 、 potassium tert-butylate 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 50.0 ℃ 、6.0 MPa 条件下， 以99 %的产率得到(1R,4R)-1-(2-chlorophenyl)-4-phenylbutane-1,4-diol
  参考文献：
  名称：

  Ru催化二芳基1,4-二酮的对映选择性氢化：手性1,4-二芳基丁烷-1,4-二醇的合成

  摘要：

  使用反式-RuCl 2 [( S )-BINAP)][( S )-Daipen] 作为催化剂实现了二芳基 1,4-二酮的不对称氢化，反应产生了优异的对映选择性和非对映选择性（高达 > 99% ee和de )。该方法为手性 1,4-二芳基丁烷-1,4-二醇提供了一种方便有效的合成方法，该方法是多种手性助剂和配体的重要中间体。

  DOI：

  10.1021/acs.orglett.2c02721
• 作为产物：
  描述：

  邻氯苯乙酮 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 1-(2-chlorophenyl)-4-phenylbutane-1,4-dione
  参考文献：
  名称：

  通过连续流动的氯乙酸克莱森反应进行酯的轻度同源

  摘要：

  报道了在连续流动装置中使用氯乙酸（CA）和LiHMDS（HMDS = hexamethyldisilazide）选择性官能化酯的氯甲基化反应。这种Claisen同源性首次扩展到使用二氯乙酸（DCA）的双氯甲基化作用，从而使人们能够探索尚未充分开发的α，α'-双氯酮。流动条件的使用能够有效地生成和反应不稳定的氯乙酸二价阴离子中间体，从而在经济的化学计量比（-10°C，<1分钟，1.0-2.4当量二价阴离子）下导致前所未有的温和且可扩展的反应条件。干净的反应曲线允许随后使用未纯化的粗产物，这在广泛关注的各种杂环的合成中得到了证明。此外，我们报道了一本小说，

  DOI：

  10.1002/anie.201810158

文献信息

• GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS
  申请人：Samumed, LLC

  公开号：US20140243349A1

  公开（公告）日：2014-08-28

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

  本公开提供了激活Wnt/β-连环蛋白信号通路并因此治疗或预防与信号转导相关的疾病的γ-二酮或其类似物；这些疾病包括骨质疏松症和骨关节病；骨发育不全、骨缺陷、骨折、牙周病、耳硬化症、伤口愈合、颅颌面缺陷、溶骨性骨病、创伤性脑损伤或脊柱损伤、与中枢神经系统分化和发育相关的脑萎缩/神经系统疾病，包括帕金森病、中风、缺血性脑疾病、癫痫、阿尔茨海默病、抑郁症、躁郁症、精神分裂症；耳部疾病如耳蜗毛细胞丧失；眼部疾病如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性以及与干细胞分化和生长相关的疾病，如脱发、造血相关疾病和组织再生相关疾病。
• Gamma-diketones for treatment and prevention of aging skin and wrinkles
  申请人：Samumed, LLC

  公开号：US10434052B2

  公开（公告）日：2019-10-08

  The present disclosure relates to compounds having the following structure: or a dermatologically acceptable salt thereof, and cosmetic or dermopharmaceutical compositions comprising the same, and methods for using the compounds or compositions for treating, protecting, and/or improving the condition and/or aesthetic appearance of skin, for example, treating, preventing, ameliorating, reducing and/or eliminating fine lines and/or wrinkles of skin, or improving the appearance of fine lines and/or or wrinkles of skin comprising application of the compounds or compositions disclosed.

  本公开涉及具有以下结构的化合物： 或其皮肤学上可接受的盐，以及包含这些化合物的化妆品或皮肤药物组合物，以及使用这些化合物或组合物治疗、保护和/或改善皮肤状况和/或美学外观的方法，例如，治疗、预防、改善、减少和/或消除皮肤细纹和/或皱纹，或改善皮肤细纹和/或或皱纹的外观，包括应用所公开的化合物或组合物。
• γ-diketones as Wnt/β-catenin signaling pathway activators
  申请人：Samumed, LLC

  公开号：US10457672B2

  公开（公告）日：2019-10-29

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

  本公开提供了γ-二酮或其类似物，它们能激活Wnt/β-catenin信号转导，从而治疗或预防与信号转导有关的疾病，如骨质疏松症和骨关节病；成骨不全症、骨缺损、骨折、牙周病、耳硬化症、伤口愈合、颅面缺损、溶瘤性骨病、脑外伤或脊柱损伤、脑萎缩/与中枢神经系统分化和发育有关的神经系统疾病，包括帕金森病、中风、缺血性脑病、癫痫、阿尔茨海默病、抑郁症、躁狂症、精神分裂症；耳部疾病，如耳蜗毛细胞缺失；眼部疾病，如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性；以及与干细胞分化和生长有关的疾病，如脱发、造血相关疾病和组织再生相关疾病。
• Gamma-diketones as wnt/β-catenin signaling pathway activators
  申请人：Samumed, LLC

  公开号：US11034682B2

  公开（公告）日：2021-06-15

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

  本公开提供了γ-二酮或其类似物，它们能激活Wnt/β-catenin信号转导，从而治疗或预防与信号转导有关的疾病，如骨质疏松症和骨关节病；成骨不全症、骨缺损、骨折、牙周病、耳硬化症、伤口愈合、颅面缺损、溶瘤性骨病、脑外伤或脊柱损伤、脑萎缩/与中枢神经系统分化和发育有关的神经系统疾病，包括帕金森病、中风、缺血性脑病、癫痫、阿尔茨海默病、抑郁症、躁狂症、精神分裂症；耳部疾病，如耳蜗毛细胞缺失；眼部疾病，如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性；以及与干细胞分化和生长有关的疾病，如脱发、造血相关疾病和组织再生相关疾病。
• Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets
  作者：Derek C. Cole、Joseph R. Stock、Rajiv Chopra、Rebecca Cowling、John W. Ellingboe、Kristi Y. Fan、Boyd L. Harrison、Yun Hu、Steve Jacobsen、Lee D. Jennings、Guixian Jin、Peter A. Lohse、Michael S. Malamas、Eric S. Manas、William J. Moore、Mary-Margaret O’Donnell、Andrea M. Olland、Albert J. Robichaud、Kristine Svenson、JunJun Wu、Eric Wagner、Jonathan Bard

  DOI：10.1016/j.bmcl.2007.12.010

  日期：2008.2

  Proteolytic cleavage of amyloid precursor protein by beta-secretase (BACE-1) and gamma-secretase leads to formation of beta-amyloid (A beta) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of A beta and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S-1 and S-2' pockets leading to submicromolar BACE-1 inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.