1,2,3,4-tetrahydro-1-methyl-1-naphthalenecarboxaldehyde | 129479-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-1-methyl-1-naphthalenecarboxaldehyde
• 英文别名: 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde；1,2,3,4-Tetrahydro-1-methylnaphthalene-1-carboxaldehyde；1-methyl-3,4-dihydro-2H-naphthalene-1-carbaldehyde
• CAS: 129479-86-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: CXGQYHJVSLVHPE-UHFFFAOYSA-N

物化性质

• 沸点：
  266.8±19.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1,2,3,4-tetrahydro-1-methyl-1-naphthalenecarboxaldehyde 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.17h， 以26.4 mg的产率得到(1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanol
  参考文献：
  名称：

  从芳族酮中获取苄基季碳

  摘要：

  在生物分子和药物中普遍存在的苄基全碳四元立体中心的构建是具有高度实际意义的任务。在这里，我们公开了一种由芳基酮构建全碳四元结构单元的高效一锅法，揭示了整个过程涉及三个连续的化学事件，即亲核加成，Meinwald 1,2-氢迁移和烷基化。有趣的是，在所采用的条件下，苯乙酮的二聚作用导致形成2，4-二芳基呋喃，而不是季碳产物。

  DOI：

  10.1021/acs.orglett.9b02204
• 作为产物：
  描述：

  1,2,3,4,-四氢-1-萘甲酸甲酯 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.67h， 生成 1,2,3,4-tetrahydro-1-methyl-1-naphthalenecarboxaldehyde
  参考文献：
  名称：

  New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase

  摘要：

  A monocyclic compound 3 (3-ethynyl-3-methyl-6-oxocyclohexa-1,4-dienecarbonitrile) is a highly reactive Michael acceptor leading to reversible adducts with nucleophiles, which displays equal or greater potency than the pentacyclic triterpenoid CDDO in inflammation and carcinogenesis related assays. Recently, reversible covalent drugs, which bind with protein targets but not permanently, have been gaining attention because of their unique features. To explore such reversible covalent drugs, we have synthesized monocyclic, bicyclic, and tricyclic compounds containing 3 as an electrophilic fragment and evaluated them as activators of the Keap1/Nrf2/ARE pathway and inhibitors of iNOS. Notably, these compounds maintain the unique features of the chemical reactivity and biological potency of 3. Among them, a monocyclic compound 5 is the most potent in these assays while a tricyclic compound 14 displays a more robust and specific activation profile compared to 5. In conclusion, we demonstrate that 3 is a useful electrophilic fragment for exploring reversible covalent drugs.

  DOI：

  10.1021/acs.jmedchem.5b00393

文献信息

• High-purity (fluoroalkyl)benzene derivative and process for producing the same
  申请人：Hidaka Toshio

  公开号：US20060167324A1

  公开（公告）日：2006-07-27

  The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

  本发明生产(氟烷基)苯衍生物的过程包括以下步骤：将烷基苯衍生物中3至12族过渡金属的总含量以金属原子计减少至500 ppm或以下；通过光卤化反应卤化纯化后的烷基苯衍生物的支链烷基，得到(卤烷基)苯衍生物；使用10摩尔或更高量的HF对(卤烷基)苯衍生物进行卤素-氟交换。本发明生产的(氟烷基)苯衍生物中杂质含量如残留卤素和残留金属得到了降低，可用作功能化学产品的中间体，用于药品和电子材料等应用。
• Tricyclic aromatase inhibitors
  申请人：Akzo N.V.

  公开号：US05019585A1

  公开（公告）日：1991-05-28

  The invention relates to tricyclic aromatase inhibitors, their preparation and their use in a pharmaceutical preparation. The compounds according to the invention possess the general formula I ##STR1## wherein R.sup.1 and R.sup.2 independently of one another denote H, halogen, alkyl, alkoxy, alkylthio, OH, CN, CF.sub.3, NO.sub.2, an amino group which is unsubstituted or substituted by alkyl, an NHacyl group, carbonamide or a free or esterified carboxylate group; R.sup.3 is H, alkyl, alkoxyalkyl or arylalkyl; R.sup.4 is H, OH, alkoxy or arylalkoxy; m is 1 or 2; n is 2, 3 or 4; the broken line represents an optional bond; Q denotes ##STR2## with the proviso that when R.sup.1 and R.sup.2 are H, halogen, alkyl, alkoxy or OH, m=1, n=3, the broken line does not represent a bond and Q is imidazolyl, R.sup.3 and R.sup.4 may not both be H; and also pharmaceutically acceptable salts.

  本发明涉及三环芳香族酶抑制剂、它们的制备以及它们在制药制剂中的使用。该发明的化合物具有一般式I 其中R1和R2分别独立地表示H、卤素、烷基、烷氧基、烷硫基、OH、CN、CF3、NO2、未取代或取代的烷基氨基、NHacyl基、羰基或自由或酯化羧酸基；R3表示H、烷基、烷氧基烷基或芳基烷基；R4表示H、OH、烷氧基或芳基烷氧基；m为1或2；n为2、3或4；中间的虚线表示可选键；Q表示##STR2## 如果R1和R2是H、卤素、烷基、烷氧基或OH，m=1，n=3，虚线不表示键，并且Q是咪唑基，那么R3和R4不能同时为H；还包括药学上可接受的盐。
• HIGH-PURITY (FLUOROALKYL)BENZENE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1500641A1

  公开（公告）日：2005-01-26

  The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

  根据本发明生产(氟烷基)苯衍生物的工艺包括以下步骤：将烷基苯衍生物中第3组至第12组过渡金属的总含量降低到500ppm或更低(以金属原子计)；通过光卤化将纯化的烷基苯衍生物中的支链烷基卤化，得到（卤代烷基）苯衍生物；以及使用 HF 将（卤代烷基）苯衍生物进行卤氟交换，HF 的用量为每摩尔（卤代烷基）苯衍生物 10 摩尔或更高。该工艺制得的(氟烷基)苯衍生物的杂质（如残留卤素和残留金属）含量降低，可用作功能化学产品的中间体，应用于医药和电子材料等领域。
• Acetylenic cyanoenones as therapeutics for inflammation and carcinogenesis
  申请人：Honda Tadashi

  公开号：US10233146B2

  公开（公告）日：2019-03-19

  The present invention provides a compound having the structure: wherein X is C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, cyano, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenylaryl, alkenylheteroaryl, alkynylaryl, alkynylheteroaryl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, heteroaryloxy, acyl, alkylhydroxy, alkylamino, alkenylamino, alkynylamino, amido, carboxyl, or carboxyl ester, or forms an unsubstituted or substituted cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indane or tetralin with Y, Y is H or forms an unsubstituted or substituted cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, indane or tetralin with X, or forms an unsubstituted or substituted monocycle with Z; and Z is H or forms an unsubstituted or substituted monocycle with Y; wherein when X and Y are both H, then X is C2 alkenyl or C2 alkynyl, and when Y is H forms a substituted cyclohexyl, cycloheptyl with X, the cyclohexyl is other than a trisubstituted cyclohexyl bearing CH3, i-Pr and (CH2)2CO2CH3 groups or CH3, i-Pr and (CH2)3NH2, or a salt or ester thereof.

  本发明提供了一种具有以下结构的化合物： 其中 X是C1-C12烷基、C2-C12烯基、C2-C12炔基、氰基、芳基、杂芳基、烷芳基、烷基异芳基、烯芳基、烯基异芳基、炔芳基、炔基异芳基、烷氧基、烯氧基、炔氧基、芳氧基、杂芳氧基、酰基、烷基羟基、烷基氨基、烯基氨基、炔基氨基、氨基、羧基或羧基酯，或与 Y 形成未取代或取代的环丁基、环戊基、环己基、环庚基、茚或四萘、 Y 是 H，或与 X 形成未取代或取代的环丁基、环戊基、环己基、环庚基、茚满或四萘，或与 Z 形成未取代或取代的单环；和 Z 是 H，或与 Y 形成未取代或取代的单环； 其中，当 X 和 Y 均为 H 时，则 X 为 C2 烯基或 C2 炔基，而当 Y 为 H 时，则与 X 形成取代的环己基、环庚基，该环己基是三取代的环己基以外的环己基。 当 Y 为 H 与 X 形成取代的环己基、环庚基时，环己基不是含有 CH3、i-Pr 和 (CH2)2CO2CH3 基团或 CH3、i-Pr 和 (CH2)3NH2 的三取代环己基、 或其盐或酯。
• Chirochromism-Photochromism by Epimerization: Search for a Liquid Crystal Phototrigger
  作者：Mingbao Zhang、Gary B. Schuster

  DOI：10.1021/ja00090a033

  日期：1994.6

  A new class of photochromic reactions was investigated as a possible trigger for phase transitions in liquid crystals. Chirochromic compounds have two chiral units. One unit is fixed, and the other can be switched with light. A series of diastereomeric compounds based on ketals and acetals of 1,1'-bi-2-naphthol was prepared. In some cases, the absorption spectra of the diastereomers are measurably different. The ketals do not undergo efficient photoepimerization, apparently because the activation barrier for atropisomerism in their triplet state has increased. However, certain of the acetal derivatives do photoepimerize and are chirochromic. These compounds may be developed into triggers.