(E)-3-(6-methoxynaphthalen-2-yl) but-2-en-1-ol | 212078-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-3-(6-methoxynaphthalen-2-yl) but-2-en-1-ol
• 英文别名: (E)-3-(6-methoxy-2-naphthyl)-2-buten-1-ol；(E)-3-(6-methoxynaphthalen-2-yl)but-2-en-1-ol
• CAS: 212078-31-4
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: APCJMFKYZULBLD-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(6-methoxynaphthalen-2-yl) but-2-en-1-ol 在 1,2-环氧丁烷 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 ethyl (2E,4E,6E)-7-(6-methoxynaphthalen-2-yl)-3-methylocta-2,4,6-trienoate
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008
• 作为产物：
  描述：

  methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以65%的产率得到(E)-3-(6-methoxynaphthalen-2-yl) but-2-en-1-ol
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008

文献信息

• Fused ring compounds, process for producing the same and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06420375B1

  公开（公告）日：2002-07-16

  To provide a novel compound of the formula: [wherein A1 ix a 5 or 6-membered ring which may be substituted by a group not containing a cyclic group, A2 is an aromatic ring which may be substituted, X is a divalent group, Y is a nitrogen atom or a methine group, Z is an ethenylene which may be substituted or ethynylene, R is a heterocyclic group which may be substituted, provided that 3,4-dihydro-6-[3-(1H-imidazol-1-yl)-1-propenyl]-2(1H)-quinolone and 2-[3-[5-ethyl-6-methyl-2-(benzyloxy)-3-pyridyl]-1-propenyl]benzoxazole are excluded.], or a salt thereof which has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating mammals suffering from, for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  提供一种新颖的化合物，其化学式为： 其中A1是一个5或6成员环，可以被不含环状基团的基团取代，A2是一个芳香环，可以被取代，X是一个二价基团，Y是一个氮原子或一个亚甲基基团，Z是一个可以被取代的乙烯基或乙炔基，R是一个可以被取代的杂环基团，但不包括3,4-二氢-6-[3-(1H-咪唑-1-基)-1-丙烯基]-2(1H)-喹啉和2-[3-[5-乙基-6-甲基-2-(苄氧基)-3-吡啶基]-1-丙烯基]苯并噁唑，或其盐，具有类固醇C17,20-裂解酶抑制活性，对于预防和治疗患有原发性癌症、恶性肿瘤、其转移和复发等疾病的哺乳动物是有用的。
• Cu-Catalyzed Asymmetric Dicarboxylation of 1,3-Dienes with CO₂
  作者：Yong-Yuan Gui、Xiao-Wang Chen、Xiao-Yan Mo、Jun-Ping Yue、Rong Yuan、Yi Liu、Li-Li Liao、Jian-Heng Ye、Da-Gang Yu

  DOI：10.1021/jacs.3c14146

  日期：2024.2.7

  it is still highly challenging and limited to generation of achiral or racemic dicarboxylic acids. To date, catalytic asymmetric dicarboxylation with CO2 to give chiral dicarboxylic acids has not been reported. Herein, we report the first asymmetric dicarboxylation of 1,3-dienes with CO2 via Cu catalysis. This strategy provides an efficient and environmentally benign route to chiral dicarboxylic acids

  二羧酸及其衍生物是有机合成、生物化学和聚合物工业的重要组成部分。尽管CO 2催化二羧化代表了一种直接且可持续的二羧酸途径，但它仍然具有高度挑战性，并且仅限于生成非手性或外消旋二羧酸。迄今为止，尚未报道用CO 2催化不对称二羧化反应生成手性二羧酸。在此，我们首次报道了通过 Cu 催化 1,3-二烯与 CO 2发生不对称二羧化反应。该策略提供了一种高效且环境友好的途径来制备具有高区域选择性、化学选择性和对映选择性的手性二羧酸。铜自中继催化，即铜催化 1,3-二烯硼羧化生成羧化烯丙基硼酸酯中间体，随后 C-B 键羧化生成二羧酸酯，是这种双羧化成功的关键。此外，该方案具有广泛的底物范围、良好的官能团耐受性、易于产物衍生化以及手性液晶聚酯和类药物支架的容易合成。
• FUSED RING COMPOUNDS, PROCESS FOR PRODUCING THE SAME AND USE THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0974584B1

  公开（公告）日：2003-01-15
• US6420375B1
  申请人：——

  公开号：US6420375B1

  公开（公告）日：2002-07-16
• Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part
  作者：George E. Magoulas、Stavros E. Bariamis、Constantinos M. Athanassopoulos、Anastasios Haskopoulos、Petros G. Dedes、Marios G. Krokidis、Nikos K. Karamanos、Dimitris Kletsas、Dionissios Papaioannou、George Maroulis

  DOI：10.1016/j.ejmech.2010.12.008

  日期：2011.2

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.