5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde | 136759-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde
• 英文别名: 2-Formyl-5-methoxy-1-tetralon；2-formyl-5-methoxy-1-tetralone；5-methoxy-1-oxo-3,4-dihydro-2H-naphthalene-2-carbaldehyde
• CAS: 136759-10-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: MTXHQLZDDPFKIF-UHFFFAOYSA-N

物化性质

• 沸点：
  379.3±42.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde 在 chromium(VI) oxide 、 氢溴酸 、 sodium acetate 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 大黄酸
  参考文献：
  名称：

  A new synthesis of Rhein

  摘要：

  A novel synthesis of Rhein (2), the active metabolite of the anti-osteoarthritic drug Diacetyl Rhein (1) has been achieved. Key steps include stereospecific olefination of aldehyde 21 with novel phosphonate 28 and the cyclisation of acid 31 to produce anthracene 32.

  DOI：

  10.1016/s0040-4039(00)76534-8
• 作为产物：
  描述：

  甲酸甲酯 、 5-甲氧基-3,4-二氢-2H-1-萘酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde
  参考文献：
  名称：

  A new synthesis of Rhein

  摘要：

  A novel synthesis of Rhein (2), the active metabolite of the anti-osteoarthritic drug Diacetyl Rhein (1) has been achieved. Key steps include stereospecific olefination of aldehyde 21 with novel phosphonate 28 and the cyclisation of acid 31 to produce anthracene 32.

  DOI：

  10.1016/s0040-4039(00)76534-8

文献信息

• The Quinary Catalyst–Substrate Complex Induced Construction of Spiro-Bridged or Cagelike Polyheterocyclic Compounds via a Substrate-Controlled Cascade Process
  作者：Chen Wang、Ying-Han Chen、Hui-Chun Wu、Cong Wang、Yan-Kai Liu

  DOI：10.1021/acs.orglett.9b02375

  日期：2019.9.6

  The asymmetric organocatalytic cascade reaction of cyclic β-oxo aldehydes to 2-hydroxycinnamaldehydes is developed. The bifunctional tertiary amine-thiourea catalyst was used in a rationally designed multiple catalysis where the asymmetric iminium catalysis and thiourea anion-binding catalysis were combined by carboxylate anion as a ternary catalytic system to form a quinary catalyst-substrate complex

  研究了环状β-氧代醛与2-羟基肉桂醛的不对称有机催化级联反应。双官能叔胺-硫脲催化剂用于合理设计的多重催化中，其中不对称的亚胺鎓催化和硫脲阴离子结合催化通过羧酸根阴离子作为三元催化体系结合在一起，形成了五元催化剂-底物配合物，为富含对映体的螺桥或笼状多杂环化合物的构建。催化剂的再利用也已成功实现。
• Pyrimidine derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05753663A1

  公开（公告）日：1998-05-19

  The disclosed pyrimidine derivatives, and pharmaceutically acceptable salts thereof, exhibit useful pharmacological properties, in particular use as 5HT.sub.2C - antagonists. The invention is also directed to formulations and methods for treatment.

  所披露的嘧啶衍生物及其药学上可接受的盐具有有用的药理特性，特别是作为5HT.sub.2C拮抗剂的用途。本发明还涉及治疗的配方和方法。
• Phenylethanolaminomethyltetralins and pharmaceutical use
  申请人：Sanofi

  公开号：US05130339A1

  公开（公告）日：1992-07-14

  New phenylethanolaminomethyltetralins of formula (I) ##STR1## wherein E represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro, halogen, or trifluoromethyl, L represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkyoxy, phenyl, nitro, or halogen, or E and L taken together represent a group --CH.dbd.CH--CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, and G represents hydrogen, chloro, hydroxy or an --OG' group wherein G' represents a (C.sub.1 -C.sub.4 (alkyl group either unsubstituted or substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, carboxy, or (C.sub.3 -C.sub.7)cycloalkyl; a (C.sub.3 -C.sub.7)cycloalkyl group; or a (C.sub.2 -C.sub.4)alkanoyl group; and salts thereof, are described which showed to be active as intestinal motility modulating agents and intraocular hypertension lowering agents. Also described is a process for the preparation of the new compounds and the intermediates of formula (III) ##STR2## employed in said process.

  化合物公式为(I)的新苯乙醇胺基甲基四氢萘，其中E代表氢，(C1-C4)烷基，(C1-C4)烷氧基，苯基，硝基，卤素或三氟甲基，L代表氢，(C1-C4)烷基，(C1-C4)烷氧基，苯基，硝基或卤素，或E和L在一起代表一个基团--CH=CH-CH=CH-或--CH2-CH2-CH2-CH2-，G代表氢，氯，羟基或-OG'基团，其中G'代表(C1-C4)烷基，未取代或取代羟基，(C1-C4)烷氧基，(C1-C4)烷氧羰基，羧基或(C3-C7)环烷基；(C3-C7)环烷基；或(C2-C4)烷酰基；以及其盐，这些化合物表现出作为肠动力调节剂和降低眼内压的活性。还描述了制备新化合物和公式(III)的中间体的过程，该中间体在所述过程中使用。
• PYRIMIDINE DERIVATIVES AS 5HT2C RECEPTOR ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0856001B1

  公开（公告）日：2002-08-28
• Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1-Oxotetralin-2-carbaldehyde to <i>ortho</i>-Hydroxyphenyl-Substituted <i>para</i>-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins
  作者：Zhi-Pei Zhang、Li Chen、Xin Li、Jin-Pei Cheng

  DOI：10.1021/acs.joc.7b03177

  日期：2018.3.2

  A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed by an oxidation was developed. The reactions proceeded smoothly with a wide range of p-QMs and 1-oxotetralin-2-carbaldehydes to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee).