ethyl 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propionate | 108299-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: ethyl 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propionate
• 英文别名: ethyl 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate；3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid ethyl ester；3-(1-Oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionsaeure-aethylester；2-(2-Ethoxycarbonylethyl)-3,4-dihydro-1(2H)-naphthalenone；ethyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalene-propanoate；ethyl 3-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)propanoate
• CAS: 108299-30-5
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: GRXHCNGPFAOIPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  182-183 °C(Press: 6 Torr)
• 密度：
  1.1206 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  ethyl 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propionate 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 5.0h， 以96%的产率得到3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid
  参考文献：
  名称：

  Construction of Fused Cyclooctanoid Ring Systems via Seven-Membered Ring Carbonyl Ylides

  摘要：

  一系列连接到环戊酮/环己酮/1-四氢萘酮单元的α-重氮羰基化合物通过使用重氮甲烷溶液，通过铑产生的羰基叶立德构建了各种融合的环辛烷环体系。铑(II)醋酸二聚体与各种α-重氮羰基化合物的反应生成了瞬态的七元环羰基叶立德，这些叶立德与亲二极体如N-苯基马来酰亚胺、对苯醌和DMAD进行了方便的1,3-偶极环加成反应，以串联方式提供了多种融合的环氧桥接环辛烷环体系。有趣的是，通过七元环羰基叶立德的分子内质子转移生成了一个oxepine环体系。当对苯醌作为亲二极体时，得到了一个三氧杂多环化合物。报道了对融合环辛烷类衍生物的单晶X射线分析，以明确确定融合环氧桥接环辛烷环体系的结构和立体化学；进一步分析揭示了固态结构中存在的独特分子间C-H···π相互作用模式。

  DOI：

  10.1246/bcsj.75.801
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 42.0h， 生成 ethyl 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propionate
  参考文献：
  名称：

  还原吲哚制备六氢咔唑衍生物

  摘要：

  在亚胺离子中间体的阶段，通过用氢化硼酸盐试剂还原而中断了苯基肼衍生物的费歇尔吲哚化，在位置4a提供了具有官能化侧链的六氢咔唑衍生物。用于该转化的环状δ-氧代酯是从丙烯酸乙酯和环烷酮获得的。

  DOI：

  10.1002/ejoc.202001226

文献信息

• Construction of Fused Cyclooctanoid Ring Systems via Seven-Membered Ring Carbonyl Ylides
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan、Eringathodi Suresh、Parthasarathi Dastidar

  DOI：10.1246/bcsj.75.801

  日期：2002.4

  A series of α-diazo carbonyl compounds tethered to cyclopentanone/cyclohexanone/1-tetralone units have been synthesized using a diazomethane solution to construct various fused cyclooctane ring systems via rhodium-generated carbonyl ylides. The reaction of rhodium(II) acetate dimer with various α-diazo carbonyl compounds generated transient cyclic seven-membered ring carbonyl ylides, which underwent facile 1,3-dipolar cycloadditions with dipolarophiles, like N-phenylmaleimide, p-benzoquinone, and DMAD to furnish a variety of fused epoxy-bridged cyclooctane ring systems in a tandem manner. Interestingly, an oxepine ring system was generated via an intramolecular proton transfer of a seven-membered ring carbonyl ylide. A tri-oxa polycyclic compound was obtained in the case of p-benzoquinone as dipolarophile. A single-crystal X-ray analysis of a fused cyclootanoid derivative is reported to decisively establish the structure and stereochemistry of the fused epoxy-bridged cyclooctane ring systems; a further analysis revealed the existence of a unique intermolecular C–H···π interaction motif in the solid-state architecture.

  一系列连接到环戊酮/环己酮/1-四氢萘酮单元的α-重氮羰基化合物通过使用重氮甲烷溶液，通过铑产生的羰基叶立德构建了各种融合的环辛烷环体系。铑(II)醋酸二聚体与各种α-重氮羰基化合物的反应生成了瞬态的七元环羰基叶立德，这些叶立德与亲二极体如N-苯基马来酰亚胺、对苯醌和DMAD进行了方便的1,3-偶极环加成反应，以串联方式提供了多种融合的环氧桥接环辛烷环体系。有趣的是，通过七元环羰基叶立德的分子内质子转移生成了一个oxepine环体系。当对苯醌作为亲二极体时，得到了一个三氧杂多环化合物。报道了对融合环辛烷类衍生物的单晶X射线分析，以明确确定融合环氧桥接环辛烷环体系的结构和立体化学；进一步分析揭示了固态结构中存在的独特分子间C-H···π相互作用模式。
• Biogenic amine uptake inhibitors
  申请人：Abbott Laboratories

  公开号：US05180733A1

  公开（公告）日：1993-01-19

  Compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein M is 0, 1 or 2 and n is 0 or 1; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.1 -C.sub.6 -alkyl substituted with a heterocyclic group or C.sub.7 -C.sub.16 -arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxy, amino and C.sub.1 -C.sub.6 -alkylamino; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, halogen, and halo-C.sub.1 -C.sub.6 -alkyl, or any two of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 taken together form a methylenedioxy group; and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl. These compounds are useful as inhibitors of the neuronal uptake of biogenic amines and for the treatment of affective disorders, such as, for example, depression.

  该公式化合物为：##STR1##或其药学上可接受的盐，其中M为0、1或2，n为0或1；R.sup.1为氢或较低的烷基；R.sup.2为C.sub.1 -C.sub.6 -烷基，其上取代有杂环基团或C.sub.7 -C.sub.16 -芳基烷基，其中芳基未取代或取代有1至3个非氢成员，独立选择自卤素、C.sub.1 -C.sub.6 -烷基、卤代C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.6 -烷氧基、羟基、氨基和C.sub.1 -C.sub.6 -烷基氨基；R.sup.3、R.sup.4、R.sup.5和R.sup.6分别选自氢、C.sub.1 -C.sub.6 -烷氧基、C.sub.1 -C.sub.6 -烷基、卤素和卤代C.sub.1 -C.sub.6 -烷基的群，或R.sup.3、R.sup.4、R.sup.5和R.sup.6中的任意两个一起形成亚甲二氧基基团；R.sup.7为氢或C.sub.1 -C.sub.6 -烷基。这些化合物可用作生物胺神经元摄取抑制剂，用于治疗情感障碍，例如抑郁症。
• Biogentic amine uptake inhibitors
  申请人：Abbott Laboratories

  公开号：US05248677A1

  公开（公告）日：1993-09-28

  Compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein m is 0, 1 or 2 and n is 0 or 1; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.1 -C.sub.6 -alkyl substituted with a heterocyclic group or C.sub.7 -C.sub.16 -arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxy, amino and C.sub.1 -C.sub.6 -alkylamino; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, halogen, and halo-C.sub.1 -C.sub.6 -alkyl, or any two of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 taken together form a methylenedioxy group; and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl. These compounds are useful as inhibitors of the neuronal uptake of biogenic amines and for the treatment of affective disorders, such as, for example, depression.

  该式化合物为：##STR1## 或其药用可接受的盐，其中m为0、1或2，n为0或1；R.sup.1为氢或较低的烷基；R.sup.2为C.sub.1-C.sub.6-烷基，其上取代有杂环基团或C.sub.7-C.sub.16-芳基烷基，其中芳基未取代或取代有1至3个非氢成员，独立选自卤素、C.sub.1-C.sub.6-烷基、卤代C.sub.1-C.sub.6-烷基、C.sub.1-C.sub.6-氧烷基、羟基、氨基和C.sub.1-C.sub.6-烷基氨基；R.sup.3、R.sup.4、R.sup.5和R.sup.6独立选自氢、C.sub.1-C.sub.6-氧烷基、C.sub.1-C.sub.6-烷基、卤素和卤代C.sub.1-C.sub.6-烷基，或R.sup.3、R.sup.4、R.sup.5和R.sup.6中的任意两个组成亚甲二氧基基团；R.sup.7为氢或C.sub.1-C.sub.6-烷基。这些化合物可用作生物胺神经元摄取抑制剂，用于治疗情感障碍，例如抑郁症。
• 1-\x9b.omega.-(3,4-dihydro-2-naphthalenyl)alkyl!-cyclic amine derivatives,
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05847159A1

  公开（公告）日：1998-12-08

  1-\x9b.omega.-(3,4-Dihydro-2-naphthalenyl)alkyl!cyclic amine derivative of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are H, halogen, OH, alkyl, alkoxy, hydroxymethyl, etc., or R.sup.1 and R.sup.2 combine to form methylenedioxy, trimethylene, etc., R.sup.3 is H, etc., R.sup.4 is H, OH, alkyl, etc., R.sup.5 is H, alkyl, etc., p is integer of from 2 to 6, and q is integer of from 3 to 7, provided that when p is 2, and q is 5, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are not simultaneously H, or salts thereof, or N-oxide derivatives thereof, or a process for preparing the same, or pharmaceutical composition containing the same. The compounds of the present invention show potent inhibitory effect on the micturition reflex, and are useful as agents for treatment of frequent urination and urinary incontinence.

  化合物的式(I)为：1-\x9b.omega.-(3,4-二氢-2-萘基)烷基!环状胺衍生物，其中R.sup.1和R.sup.2为H、卤素、OH、烷基、烷氧基、羟甲基等，或R.sup.1和R.sup.2结合形成亚甲二氧基、三亚甲基等，R.sup.3为H等，R.sup.4为H、OH、烷基等，R.sup.5为H、烷基等，p为2到6的整数，q为3到7的整数，但当p为2，q为5时，R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5不能同时为H，或其盐，或其N-氧化物衍生物，或制备它们的方法，或包含它们的制药组合物。本发明化合物表现出强效的抑制排尿反射的作用，可用作治疗频繁排尿和尿失禁的药物。
• DBU Promoted Deformylative/Dehalogenative Difunctionalization to Access β‐Bromovinyl Aldehydes Derived from Tetralones**
  作者：Madan Sau、Sapana Dubey、Shreya Roy、Shubhankar Samanta、Tapas Das

  DOI：10.1002/ejoc.202300788

  日期：——

  Metal-free deformylative/dehalogenative carbonylation, Michael addition of β-bromovinyl aldehydes for the synthesis of δ-oxo esters and vinyl ethers have been reported. Nucleophilic and organo-catalytic behaviour of DBU is explored and the regeneration of the parent starting material from the vinyl ether is also highlighted.

  已经报道了无金属脱酰基/脱卤羰基化、β-溴乙烯基醛的迈克尔加成用于合成 δ-氧代酯和乙烯基醚。探索了 DBU 的亲核和有机催化行为，并重点介绍了乙烯基醚母体原料的再生。