1-(1H-苯并咪唑-1-基)丙酮 | 294199-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(1H-苯并咪唑-1-基)丙酮
• 英文名称: 1-(1H-benzimidazol-1-yl)propan-2-one
• 英文别名: 1-(benzimidazol-1-yl)-propan-2-one；Benzimidazo-1-ylacetone；1-benzoimidazol-1-yl-propan-2-one；1-(2-Oxo-propyl)-benzimidazol；1-(benzimidazol-1-yl)propan-2-one
• CAS: 294199-10-3
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD12145793
• 分子量: 174.202
• InChiKey: LKIVJBZMVMCCCL-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: toluene (108-88-3))
• 沸点：
  328.0±44.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(1H-苯并咪唑-1-基)丙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以71%的产率得到(±)-1-(1H-benzimidazol-1-yl)propan-2-ol
  参考文献：
  名称：

  脂肪酶催化的新型抗真菌N取代苯并咪唑衍生物的动力学拆分

  摘要：

  合成了一系列新的N取代的苯并咪唑衍生物，并评估了其对白色念珠菌的抗真菌活性。化学步骤包括合成含有苯并咪唑环的适当酮，将酮还原为外消旋醇，以及将醇乙酰化为酯。所有苯并咪唑衍生物均在较短时间内以令人满意的收率获得。所有合成的化合物均对白念珠菌具有显着的抗真菌活性900028 ATCC（0.25μg浓度下的细胞抑制百分比> 98％）。此外，醇的外消旋混合物通过脂肪酶催化的动力学拆分而分离。在酶促步骤中，进行了酯交换反应，并研究了脂肪酶类型和溶剂对反应对映选择性的影响。选择性最高的酶是荧光假单胞菌的Novozyme SP 435和脂肪酶Amano AK （E> 100）。手性28：347–354，2016。©2016 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22591
• 作为产物：
  描述：

  苯并咪唑 、 一氯丙酮 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以74%的产率得到1-(1H-苯并咪唑-1-基)丙酮
  参考文献：
  名称：

  Studies with Functionally Substituted Heteroaromatics: The Chemistry of N-Phenylhydrazonylalkylpyridinium Salts and of Phenylhydrazonylalkylbenzoazoles

  摘要：

  2-吡啶-1-基氢氯酸铵乙腈溴化物1a和2-吡啶-1-基-1-苯基乙酮溴化物1b与苯胺二氮盐氯化物反应生成相应的苯基肼酮3a和3b。类似地，化合物2a-c也与芳基二氮盐氯化物结合，生成了芳基肼酮10a和10b，这些化合物用于合成azolypyridazinones 11a和11b。化合物3a和3b在氨基乙酸铵存在下在乙腈中回流转化为1,2,4,5-四氢四嗪4a和4b。在二甲基甲酰胺中回流3a则形成了3-氰基吲唑6。化合物3a在处理与酮胺化合物7后转化为吡唑8，并在二噁烷/乙腈中加热生成肼基溴化物9。化合物12是通过10b与醇性氢氧化钠反应合成的。

  DOI：

  10.1055/s-2000-6326

文献信息

• Studies with Functionally Substituted Heteroaromatics: The Chemistry of N-Phenylhydrazonylalkylpyridinium Salts and of Phenylhydrazonylalkylbenzoazoles
  作者：Mervat Mohammed Abdel-Khalik、Mohammed Hilmy Elnagdi、Samia Michel Agamy

  DOI：10.1055/s-2000-6326

  日期：——

  2-Pyrid-1-yliniumacetonitrile bromide 1a and 2-pyrid-1-ylinium-1-phenylethanone bromide 1b coupled with benzenediazonium chloride to yield the corresponding phenylhydrazones 3a, b. Similarly, compounds 2a-c also coupled with aryldiazonium chloride, yielding the arylhydrazones 10a-b, which were used as precursors for the synthesis of azolypyridazinones 11a, b. Compounds 3a, b were converted into 1,2,4,5-dihydrotetrazines 4a, b on refluxing in acetonitrile in the presence of ammonium acetate. Refluxing 3a in dimethylformamide resulted in the formation of the 3-cyanoindazole 6. Compound 3a was converted to pyrazole 8 on treatment with the enaminone 7, and to hydrazonyl bromide 9 on heating in dioxane/acetonitrile. Compound 12 was synthesized from the reaction of 10b with ethanolic aqueous sodium hydroxide.

  2-吡啶-1-基氢氯酸铵乙腈溴化物1a和2-吡啶-1-基-1-苯基乙酮溴化物1b与苯胺二氮盐氯化物反应生成相应的苯基肼酮3a和3b。类似地，化合物2a-c也与芳基二氮盐氯化物结合，生成了芳基肼酮10a和10b，这些化合物用于合成azolypyridazinones 11a和11b。化合物3a和3b在氨基乙酸铵存在下在乙腈中回流转化为1,2,4,5-四氢四嗪4a和4b。在二甲基甲酰胺中回流3a则形成了3-氰基吲唑6。化合物3a在处理与酮胺化合物7后转化为吡唑8，并在二噁烷/乙腈中加热生成肼基溴化物9。化合物12是通过10b与醇性氢氧化钠反应合成的。
• <i>N</i>-Azolylmethyl ketones as building blocks in heterocyclic synthesis: Synthesis of new polyfunctionally substituted azolylarylazophenols, azolylpyridones and azolylthiophenes
  作者：Balkis Al-Saleh、Morsy Ahmed El-Apasery、Mervat Mohammed Abdelkhalik、Mohammed Hilmy Elnagdi

  DOI：10.1002/jhet.5570400125

  日期：2003.1

  2-arylhydrazonopropanals 3a-c to yield polyfunctionally substituted azolylarylazophenols 5 and 8. The reaction of 1b and 2 with phenylisothiocyanate in the presence of α-haloketones afforded the azolylthiophenes 12a,b and 13a,b. The reaction of 20 with α-haloketone afforded 5-benzotriazol-1-yl-6-methyl-2-(2-oxopropylsulfanyl)nicotinonitrile 21 that was utilized as building blocks for the synthesis of condensed

  标题化合物1a-b和2与2-芳基肼基丙醛3a-c反应，得到多官能取代的偶氮基芳基偶氮苯酚5和8。1b和2与苯基异硫氰酸酯在α-卤代酮存在下反应，得到偶氮基噻吩12a，b和13a，b。 。20与α-卤代酮的反应提供了5-苯并三唑-1-基-6-甲基-2-（2-氧丙基硫基）烟腈21，其被用作合成缩合吡啶的结构单元。将化合物21与二甲基甲酰胺二甲基缩醛缩合，得到噻吩并[2，3 - b ]吡啶-3-基-N，N-二甲基甲am衍生物22。将其进一步用氢化钠环化成1 H-二硫代[2，3- b]。4,5- b'] dipyridin-4-one衍生物23。
• Synthesis of new azolyl azoles and azinyl azoles
  作者：Balkis Al-Saleh、Morsy Ahmed El-Apasery、Mohamed Hilmy Elnagdi

  DOI：10.1002/jhet.5570420402

  日期：2005.5

  Synthesis of new azolyl azoles and azinyl azoles from the reaction of compounds 1, 4 and 7 with phenyl isothiocyanate is reported. Compound 10 reacts with benzene diazonium chloride to yield either phenylhy-drazones 11 and 12 or the triazoloquinoline 13.

  据报道，由化合物1、4和7与异硫氰酸苯酯的反应合成了新的偶氮基唑和氮杂唑。化合物10与苯重氮氯化物反应，生成苯基氢dra 11和12或三唑并喹啉13。
• Arylalkylamine Compound and Process for Preparing the Same
  申请人：Miyazaki Hiroshi

  公开号：US20070225296A1

  公开（公告）日：2007-09-27

  The present invention relates to an arylalkylamine compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof, a process for preparing the same, and use of the above-mentioned compound as an activating compound (CaSR agonist) of a Ca sensing receptor, a pharmaceutical composition containing the above-mentioned compound as an effective ingredient, etc. The symbols in the formula represent the following meanings: Ar: optionally substituted aryl or optionally substituted heteroaryl here, the cyclic portion of the heteroaryl is bicyclic heterocyclic ring in which 5- to 6-membered monocyclic heterocyclic ring containing 1 or 2 hetero atom(s) and benzene ring are fused; R 1 : a group selected from the group consisting of optionally substituted cyclic hydrocarbon group, and optionally substituted heterocyclic group; n: an integer of 1 to 3; X: single bonding arm, —CH 2 —, —CO—, —(CH 2 ) m —CO—, —CH(R 2 )—CO—, —(CH 2 ) p —Y—(C(R 3 )(R 4 )) q —CO—, —NH—CO— or —N(R 5 )—CO—; in the above-mentioned respective definitions of the X, the bonding arm described at the left end represents a bond with R 1 ; m is an integer of 1 to 3; p is an integer of 0 to 2; q is an integer of 0 to 2; Y: —O— or —SO 2 —; R 2 : phenyl or lower alkyl; R 3 , R 4 : each independently represents hydrogen atom or lower alkyl; R 5 : lower alkyl; provided that the ring portion of the group represented by R 1 is neither naphthylidine nor partially saturated group thereof, and, when X is —CH 2 — or —CO—, R 1 is not naphthyl.

  本发明涉及一种由以下公式[I]表示的芳基烷基胺化合物或其药学上可接受的盐，其制备方法，以及上述化合物作为钙感受受体的激活化合物（CaSR激动剂），以及含有上述化合物作为有效成分的制药组合物等的用途。公式中的符号表示以下含义：Ar：此处为可选取代的芳基或可选取代的杂环芳基，其中杂环的环部分是一个含有1或2个杂原子的5-至6元单环杂环，与苯环融合；R1：选自可选取代的环烃基团和可选取代的杂环基团的群；n：1至3的整数；X：单键臂、—CH2—、—CO—、—（CH2）m—CO—、—CH（R2）—CO—、—（CH2）p—Y—（C（R3）（R4））q—CO—、—NH—CO—或—N（R5）—CO—；在上述各定义的X中，左端所描述的键臂表示与R1的键；m为1至3的整数；p为0至2的整数；q为0至2的整数；Y：—O—或—SO2—；R2：苯基或低碳烷基；R3、R4：各自独立地表示氢原子或低碳烷基；R5：低碳烷基；前提是由R1表示的基团的环部分既不是萘亚甲基也不是其部分饱和基团，且当X为—CH2—或—CO—时，R1不是萘基。
• ARYLALKYLAMINE COMPOUND AND PROCESS FOR PREPARING THE SAME
  申请人：MIYAZAKI Hiroshi

  公开号：US20100249049A1

  公开（公告）日：2010-09-30

  The present invention relates to an arylalkylamine compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof, a process for preparing the same, and use of the above-mentioned compound as an activating compound (CaSR agonist) of a Ca sensing receptor, a pharmaceutical composition containing the above-mentioned compound as an effective ingredient, etc. The symbols in the formula represent the following meanings: Ar: optionally substituted aryl or optionally substituted heteroaryl here, the cyclic portion of the heteroaryl is bicyclic heterocyclic ring in which 5- to 6-membered monocyclic heterocyclic ring containing 1 or 2 hetero atom(s) and benzene ring are fused; R 1 : a group selected from the group consisting of optionally substituted cyclic hydrocarbon group, and optionally substituted heterocyclic group; n: an integer of 1 to 3; X: single bonding arm, —CH 2 —, —CO—, —(CH 2 ) m —CO—, —CH(R 2 )—CO—, —(CH 2 ) p —Y—(C(R 3 )(R 4 )) q —CO—, —NH—CO— or —N(R 5 )—CO—; in the above-mentioned respective definitions of the X, the bonding arm described at the left end represents a bond with R 1 ; m is an integer of 1 to 3; p is an integer of 0 to 2; q is an integer of 0 to 2; Y: —O— or —SO 2 —; R 2 : phenyl or lower alkyl; R 3 , R 4 : each independently represents hydrogen atom or lower alkyl; R 5 : lower alkyl; provided that the ring portion of the group represented by R 1 is neither naphthylidine nor partially saturated group thereof, and, when X is —CH 2 — or —CO—, R 1 is not naphthyl.

  本发明涉及一种由下式[I]表示的芳基烷基胺化合物或其药学上可接受的盐，制备该化合物的方法，以及上述化合物作为钙感受受体（CaSR激动剂）的激活化合物、包含上述化合物作为有效成分的药物组合物等的用途。式中符号表示以下含义：Ar：可选取的取代芳基或可选取的取代杂环芳基，在此，所述杂环的环状部分是由1或2个杂原子的5-6元单环杂环与苯环融合而成的双环杂环；R1：选自可选取的取代环烃基团和可选取的取代杂环基团的群；n：为1至3的整数；X：单键连接臂，-CH2-，-CO-，-(CH2)m-CO-，-CH(R2)-CO-，-(CH2)p-Y-(C(R3)(R4))q-CO-，-NH-CO-或-N(R5)-CO-；在上述X的各自定义中，左端所述连接臂表示与R1的键合；m为1至3的整数；p为0至2的整数；q为0至2的整数；Y：-O-或-SO2-；R2：苯基或低碳烷基；R3，R4：各自独立地表示氢原子或低碳烷基；R5：低碳烷基；所述R1表示的基的环部分既不是萘亚甲基基团，也不是其部分饱和基团，当X为-CH2-或-CO-时，R1不是萘基。