3-(3,4-二氯苯基)丙-2-炔-1-醛 | 1010684-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3,4-二氯苯基)丙-2-炔-1-醛
• 英文名称: 3-(3,4-dichlorophenyl)-2-propynal
• 英文别名: 3-(3,4-dichlorophenyl)prop-2-yn-1-al；3-(3,4-dichlorophenyl)prop-2-ynal
• CAS: 1010684-85-1
• 化学式: C₉H₄Cl₂O
• 分子量: 199.036
• InChiKey: NOISOSBHCJFYHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(3,4-二氯苯基)丙-2-炔-1-醛 、 烯丙基溴化镁 在 水 、 甲基叔丁基醚 、 Sodium sulfate-III 、 ethyl acetate heptane 作用下， 以 四氢呋喃 为溶剂， 反应 2.42h， 以afforded the desired homoallylic alcohol (5.86 g; 24.3 mmol; 75%)的产率得到1-(3,4-二氯苯基)己-5-烯-1-炔-3-醇
  参考文献：
  名称：

  Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use

  摘要：

  本发明提供了新型芳基双环[3.1.0]己基胺，以及制备这些化合物的相关过程和中间体，以及使用这些化合物的组合物和方法，用于治疗和/或预防中枢神经系统（CNS）疾病，包括但不限于抑郁症和焦虑症。

  公开号：

  US20080194696A1
• 作为产物：
  描述：

  3,4-二氯碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3-(3,4-二氯苯基)丙-2-炔-1-醛
  参考文献：
  名称：

  WO2008/31771

  摘要：

  公开号：

文献信息

• Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines
  作者：José Alemán、Alberto Fraile、Leyre Marzo、José Luis García Ruano、Cristina Izquierdo、Sergio Díaz-Tendero

  DOI：10.1002/adsc.201200033

  日期：2012.6.18

  The first organocatalytic enantioselective 1,3‐dipolar reaction between nitrones and alkynals catalyzed by (S)‐2‐(fluorodiphenylmethyl)pyrrolidine to give 4‐isoxazolines (2,3‐dihydroisoxazoles) with high enantiomeric excess, excellent yields and low catalyst loading (1–5 mol%) is presented. The catalytic loading could be reduced to 1 mol% with only slight increases in reaction times.

  （S）-2-（氟二苯基甲基）吡咯烷催化的硝酮与炔烃之间的第一个有机催化对映选择性1,3-偶极反应，得到对映体过量高，产率高，催化剂负载低的4-异恶唑啉（2,3-二氢异恶唑）（ 1-5％（摩尔）。催化负荷可以降低到1摩尔％，而反应时间仅稍微增加。
• A new entry to highly functionalized pyrroles <i>via</i> a cascade reaction of α-amino esters and alkynals
  作者：Liang Wei、Shi-Ming Xu、Ziqi Jia、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1039/d0cc02964e

  日期：——

  Here, we developed an expedient access route to highly functionalized pyrroles from readily available α-amino acid ester hydrochlorides and alkynals via a cascade condensation/intramolecular cyclization followed by a unique C–N ester migration process. A variety of 1,2,3-trisubstituted pyrroles, which were difficult to acquire with the common methodologies, were successfully prepared in good yields

  在这里，我们通过级联缩合/分子内环化以及独特的C–N酯迁移过程，开发了从易得的α-氨基酸酯盐酸盐和炔烃到高度官能化吡咯的便捷途径。在温和的条件下，成功地以良好的收率成功制备了各种1,2,3-三取代的吡咯，这些都是用常规方法难以获得的。
• Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use
  申请人：Skolnick Phil

  公开号：US20080194696A1

  公开（公告）日：2008-08-14

  The invention provides novel arylbicyclo[3.1.0]hexylamines, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervous system (CNS) disorders, including but not limited to depression and anxiety.

  本发明提供了新型芳基双环[3.1.0]己基胺，以及制备这些化合物的相关过程和中间体，以及使用这些化合物的组合物和方法，用于治疗和/或预防中枢神经系统（CNS）疾病，包括但不限于抑郁症和焦虑症。
• CHEMICAL COMPOUNDS
  申请人：Di Fabio Romano

  公开号：US20080114049A1

  公开（公告）日：2008-05-15

  The present invention relates to (1S,6R)-6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane, pharmaceutically acceptable salts, prodrugs or solvates thereof; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as serotonin (5-HT), dopamine (DA) and norepinephrine (NE), re-uptake inhibitors.

  本发明涉及(1S,6R)-6-(3,4-二氯苯基)-1-[(甲氧基)甲基]-3-氮杂双环[4.1.0]庚烷，其药学上可接受的盐、前药或溶剂化物；用于其制备的中间体，含有它们的制药组合物以及它们在治疗中的应用，作为5-羟色胺(5-HT)、多巴胺(DA)和去甲肾上腺素(NE)的再摄取抑制剂。
• AZABICYCLIC COMPOUNDS AS INHIBITORS OF MONOAMINES REUPTAKE
  申请人：Bertani Barbara

  公开号：US20100035914A1

  公开（公告）日：2010-02-11

  The present invention relates to novel compounds of formula (I)′, and pharmaceutically acceptable salts, prodrugs or solvates thereof: wherein R 1 is hydrogen or C 1-4 alkyl; R 2 is a group A, K or W wherein A is K is an α or β naphthyl group, optionally substituted by 1 or 2 groups R 18 , each of them being the same or different; and W is and wherein G is a 5,6-membered monocyclic heteroaryl group, or a 8- to 11-membered heteroaryl bicyclic group; wherein G may be substituted by (R 15 ) p , which can be the same or different; p is an integer from 0 to 5; R 3 is selected from the group consisting of: hydrogen, fluorine, and C 1-4 alkyl; or corresponds to a group X or X 1 ; R 4 is selected from the group consisting of: hydrogen, fluorine, and C 1-4 alkyl; or corresponds to a group X or X 1 ; R 5 is hydrogen or C 1-4 alkyl; R 7 is hydrogen or C 1-4 alkyl; or is a group X, X 1 , X 2 or X 3 ; wherein X is X 1 is X 2 is and X 3 is R 6 is hydrogen or C 1-4 alkyl; or is a group X or X 1 ; R 9 is C 1-4 alkyl; R 10 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 8 is a 5-6 membered heterocycle group, which may be substituted by one or two substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy and C 1-4 alkanoyl; R 11 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 12 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 13 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 14 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 15 is selected from the group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 16 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkylC 1-3 alkyl; R 17 is hydrogen or C 1-4 alkyl; R 18 is selected from the group consisting of: halogen, cyano, and C 1-4 alkyl; R 19 is haloC 1-2 alkyl; and n is 1 or 2; with the proviso that: if R 2 is A, R 3 , R 4 , R 5 , R 6 , R 7 , R 10 , R 11 , R 13 , and R 14 are hydrogen, and R 12 is fluorine, R 1 is C 1-4 alkyl; if R 2 is A, R 3 , R 4 , R 5 , R 6 , R 7 , R 10 , R 11 , R 13 , and R 14 are hydrogen, and R 1 is methyl, R 12 is halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl or SF 5 ; or corresponds to a group R 8 ; and processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as serotonin (5-HT), dopamine (DA) and norepinephrine (NE), re-uptake inhibitors.

  本发明涉及式(I)'的新化合物，以及其药学上可接受的盐、前药或溶剂化物： 其中， R1为氢或C1-4烷基； R2为A、K或W基团，其中 A为 K为α或β萘基团，可选地被1或2个R18基团取代，每个基团相同或不同； W为 其中， G为5,6-成员单环杂芳基团或8-至11-成员杂芳双环基团；其中G可能被(R15)p取代，其中p可以是0到5的整数；R3选择自氢、氟和C1-4烷基；或对应于X或X1基团； R4选择自氢、氟和C1-4烷基；或对应于X或X1基团； R5为氢或C1-4烷基； R7为氢或C1-4烷基；或为X、X1、X2或X3基团； 其中， X为 X1为 X2为 且X3为 R6为氢或C1-4烷基；或为X或X1基团； R9为C1-4烷基； R10选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R8为5-6成员杂环基团，可以被来自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基和C1-4酰基的一或两个取代基团取代； R11选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R12选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R13选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R14选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R15选择自卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R16为氢、C1-4烷基、C3-6环烷基或C3-6环烷基C1-3烷基； R17为氢或C1-4烷基； R18选择自卤素、氰基和C1-4烷基； R19为卤代C1-2烷基；且 n为1或2； 但前提是，如果R2为A，R3、R4、R5、R6、R7、R10、R11、R13和R14为氢，而R12为氟，R1为C1-4烷基；如果R2为A，R3、R4、R5、R6、R7、R10、R11、R13和R14为氢，而R1为甲基，R12为卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基或SF5；或对应于R8基团；以及用于制备它们的过程、用于这些过程的中间体、含有它们的制药组合物以及它们在治疗中的应用，作为5-羟色胺（5-HT）、多巴胺（DA）和去甲肾上腺素（NE）的再摄取抑制剂。