6,7-Dimethoxy-naphthalene-2-carbaldehyde | 66920-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-Dimethoxy-naphthalene-2-carbaldehyde
• 英文别名: 2-formyl-6,7-dimethoxynaphthalene；6,7-Dimethoxy-2-naphthaldehyde；6,7-dimethoxy-2-formyl naphthalene；6,7-dimethoxy-2-formylnaphthalene；6,7-Dimethoxy-2-naphthaldehyd；6,7-Dimethoxynaphthalene-2-carbaldehyde
• CAS: 66920-80-7
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: RZQXUJIIEVZZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-Dimethoxy-naphthalene-2-carbaldehyde 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (3E)-4-(6,7-dimethoxynaphthalen-2-yl)but-3-en-2-ol
  参考文献：
  名称：

  具有 C4 侧链的萘衍生物的断裂反应

  摘要：

  萘或 2,3-二甲氧基萘衍生物与 Δ2-丁烯酮 (3)、Δ2-丁烯醇 (3)、3-乙酰氧基丁烯 (2)、丁醇 (3)、3-乙酰氧基丁烷和丁烷 有一个例外，侧链被分裂C4 片段。

  DOI：

  10.1002/ardp.19783110410
• 作为产物：
  描述：

  2,3-二羟基萘 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 硫酸 、 溴 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 38.0h， 生成 6,7-Dimethoxy-naphthalene-2-carbaldehyde
  参考文献：
  名称：

  一种共轭体系增大的姜黄素类似物及其制备 方法和应用

  摘要：

  本发明公开了一种共轭体系增大的姜黄素类似物及其制备方法和应用。具有如通式(I)的结构特征，其中R1为氢、甲氧基，R2为氢、羟基、甲氧基，两个萘环通过1,6‑庚二烯‑3,5‑二酮连接链连接。本发明以萘酚作为原料，合成出具有对肝癌细胞HepG2细胞增殖具有优越活性的萘环类姜黄素类似物，并且其活性优越于天然产物姜黄素。本发明的共轭体系增大的姜黄素类似物对指导前药的发现及先导化合物的设计，具有重要意义。

  公开号：

  CN105111054B

文献信息

• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane
  作者：Nolan Betterley、Sopanat Kongsriprapan、Suppisak Chaturonrutsamee、Pramchai Deelertpaiboon、Panida Surawatanawong、Manat Pohmakotr、Darunee Soorukram、Vichai Reutrakul、Chutima Kuhakarn

  DOI：10.1055/s-0036-1591545

  日期：2018.5

  Abstract Difluoro(phenylsulfanyl)methane (PhSCF2H) was found to undergo a reaction with aromatic compounds mediated by SnCl4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S,S′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature

  摘要 二氟（苯基硫基）甲烷（PhSCF 2 2H），发现发生反应与由的SnCl介导的芳族化合物4，通过一个thionium中间体，其特征在于用NMR和TD-DFT分析，导致的混合物的形成小号，小号' -二苯基二硫缩醛和芳族醛，在氧化水解后，以良好或优异的收率提供芳族醛。本发明的显着特征是含有失活酯官能团的活化芳族化合物的反应，从而以高收率得到甲酰化产物。 二氟（苯基硫基）甲烷（PhSCF 2 2H），发现发生反应与由的SnCl介导的芳族化合物4，通过一个thionium中间体，其特征在于用NMR和TD-DFT分析，导致的混合物的形成小号，小号' -二苯基二硫缩醛和芳族醛，在氧化水解后，以良好或优异的收率提供芳族醛。本发明的显着特征是含有失活酯官能团的活化芳族化合物的反应，从而以高收率得到甲酰化产物。
• Derivatives of naphthalene with comt inhibiting activity
  申请人：——

  公开号：US20040034011A1

  公开（公告）日：2004-02-19

  Compounds of formula (I′), wherein A, R 1 to R 3 and t are as defined in the disclosure, exhibit COMT enzyme inhibiting activity so that they are useful as COMT inhibitors.

  式(I′)的化合物，其中A、R1至R3和t如本公开所定义，具有COMT酶抑制活性，因此它们可用作COMT抑制剂。
• Process for producing optically active naphthalene derivative and optical resolver therefor
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06800778B1

  公开（公告）日：2004-10-05

  The present invention provides a method of producing an optically active form of a compound represented by the formula (I) having a steroid C17,20-lyase inhibitory activity and is useful as an agent for the prophylaxis or treatment of prostatism, tumor such as breast cancer, and the like or a salt thereof, which method includes reacting a mixture of optically active compounds of a naphthalene derivative represented by the formula: wherein R is a nitrogen-containing heterocyclic group, R1 is a hydrogen atom, a hydrocarbon group or an aromatic heteromonocyclic group, R2 is a hydrogen atom or a lower alkyl group, * shows the position of an asymmetric carbon, R3, R4, R5, R6, R7, R8 and R9 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group, a thiol group, an amino group, a carbamoyl group, an acyl group or a halogen atom, and R7 is bonded with R6 or R8 to form, together with a carbon atom on a naphthalene ring, a 5 or 6-membered ring containing an oxygen atom, with an optically active form of a compound represented by the formula: wherein ring A is a benzene ring, R10 and R11 are the same or different and each is a hydrogen atom, a hydrocarbon group or a halogen atom, or R10 and R11 in combination show an alkylene group, * shows the position of an asymmetric carbon, and ring B and ring C are each an aromatic ring, separating the resulting salt, and isolating the optically active form, and a novel reagent for optical resolution.

  本发明提供了一种生产一种具有类固醇C17,20-裂解酶抑制活性的化合物的光学活性形式的方法，该化合物由式（I）表示，可用作预防或治疗前列腺增生、乳腺癌等肿瘤的药物或其盐。该方法包括将由式表示的萘衍生物的光学活性化合物混合物反应：其中R是含氮杂环基团，R1是氢原子、碳氢基团或芳香族杂单环基团，R2是氢原子或较低的烷基团，*表示一个不对称碳的位置，R3、R4、R5、R6、R7、R8和R9分别独立地是氢原子、碳氢基团、羟基、硫醇基、氨基、氨基甲酰基、酰基或卤素原子，其中R7与R6或R8结合，与萘环上的碳原子一起形成一个含氧原子的5或6元环。通过与由式表示的化合物的光学活性形式反应：其中环A是苯环，R10和R11相同或不同，分别是氢原子、碳氢基团或卤素原子，或R10和R11组合成一个烷基链，*表示一个不对称碳的位置，环B和环C分别是芳香环，分离得到的盐，并分离得到光学活性形式，以及用于光学分辨的新试剂。
• C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors
  作者：Nobuyuki Matsunaga、Tomohiro Kaku、Akio Ojida、Toshimasa Tanaka、Takahito Hara、Masuo Yamaoka、Masami Kusaka、Akihiro Tasaka

  DOI：10.1016/j.bmc.2004.06.016

  日期：2004.8

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.