1-chloro-2-naphthylacetonitrile | 81250-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-chloro-2-naphthylacetonitrile
• 英文别名: 1-Chloronaphthalene-2-acetonitrile；2-(1-chloronaphthalen-2-yl)acetonitrile
• CAS: 81250-72-8
• 化学式: C₁₂H₈ClN
• 分子量: 201.655
• InChiKey: RFZXGFNZXUATFO-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±17.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloro-2-naphthylacetonitrile 在 palladium on activated charcoal PPA 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-phenyl-1,4-dihydro-3(2H)-benzoisoquinolinone
  参考文献：
  名称：

  Hazai; Deak Gy.; Doda, Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 108, # 3, p. 255 - 263

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-2-甲基-萘 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 19.5h， 生成 1-chloro-2-naphthylacetonitrile
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006

文献信息

• New bicyclic antidepressant agent. Synthesis and activity of napactadine and related compounds
  作者：James R. McCarthy、Donald L. Wright、Albert J. Schuster、Abdul H. Abdallah、Philip J. Shea、Randy Eyster

  DOI：10.1021/jm00149a031

  日期：1985.11

  A number of N,N'-dialkylarylamidines were synthesized and evaluated for antidepressant activity. Several of these compounds were synthesized from the corresponding nitriles by a new method. Slight structural modification in the series caused a marked change in biological activity and led to compounds as active as imipramine. The arylacetamidine, N,N'-dimethyl-2-naphthaleneethanimidamide hydrochloride

  合成了许多N，N′-二烷基芳基idine胺并评估了其抗抑郁活性。这些化合物中的几种是通过新方法由相应的腈合成的。系列中的轻微结构修饰导致生物学活性发生显着变化，并导致化合物的活性与丙咪嗪一样。选择芳基乙am，N，N'-二甲基-2-萘乙酰胺酰胺盐酸盐（33）（那帕他定）进行临床研究。制备了48种33的其他类似物，包括许多N-烷基am。
• HIGH PURITY 2-NAPHTHYLACETONITRILE AND METHOD FOR PRODUCING SAME
  申请人：API CORPORATION

  公开号：US20220009880A1

  公开（公告）日：2022-01-13

  High purity 2-naphthylacetonitrile with fewer impurities can be used as a starting material or intermediate for synthesizing various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, may include: subjecting 2′-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; and reacting the 2-naphthylacetic acid obtained in the subjecting, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.

  高纯度的2-萘乙腈含有较少的杂质，可用作合成各种药物产品、农药化学品和化工产品的起始物料或中间体，以及其生产方法。具有不低于95%面积百分比的2-萘乙腈的HPLC纯度，并且包含在预定面积百分比以下的由式(a)-(j)表示的萘化合物。生产高纯度2-萘乙腈的方法可能包括：在必要时在添加剂的存在下，将2'-乙酰基萘酮经Willgerodt反应，并水解得到酰胺化合物以得到2-萘乙酸；并在有机溶剂中，在必要时在催化剂的存在下，将通过上述步骤得到的2-萘乙酸、卤代试剂和磺胺酰胺反应以得到2-萘乙腈。
• Isoquinolines or benzisoquinoliner having antiinflammatory activity
  申请人：Beecham Group p.l.c.

  公开号：US04745115A1

  公开（公告）日：1988-05-17

  Compounds of the general formula I ##STR1## in which: R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-6 alkyl or together are a group X which is C.sub.3-6 polymethylene optionally in which one carbon atom is replaced by O, S or NR.sub.6 wherein R.sub.6 is hydrogen or C.sub.1-6 alkyl; R.sub.3 is a mono- or fused bi-cyclic heteroaromatic group having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur, optionally C-substituted by one or more substituents selected from halogen, CF.sub.3, nitro, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.2-7 alkanoyl or cyano; or is phenyl or naphthyl, optionally substituted by one or more substituents selected from halogen, CF.sub.3, nitro, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.2-7 alkanoyl, carboxyl, C.sub.1-6 alkoxycarbonyl, cyano, CONR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are selected from hydrogen or C.sub.1-6 alkyl or together are a group X; NR.sub.9 R.sub.10 wherein R.sub.9 and R.sub.10 are selected from hydrogen, C.sub.1-6 alkyl, C.sub.2-7 alkanoyl or C.sub.1-6 alkylsulphonyl or together are a group X; SO.sub.2 NR.sub.11 R.sub.12 wherein R.sub.11 and R.sub.12 are selected from hydrogen or C.sub.1-6 alkyl or together are a group X; or S(O).sub.m R.sub.13 wherein m is 1 or 2 and R.sub.13 is C.sub.1-6 alkyl; Z is naphthyl or a mono- or fused bicyclic heteroaromatic ring having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur or (when R.sub.3 is an optionally substituted naphthyl or heteroaromatic group as defined) Z is a phenyl ring; and Z is optionally C-substituted by one or two substituents R.sub.4 and R.sub.5 which are independently selected from C.sub.1-6 alkyl, cyano, amino, aminocarbonyl or aminocarbamoyl optionally substituted by one or two C.sub.1-6 alkyl groups or by a group X, halogen, CF.sub.3, nitro, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.2-7 alkanoyloxy or hydroxy, or together on adjacent carbon atoms are methylenedioxy or C.sub.3-5 polymethylene, are disclosed as an active therapeutic substances for the treatment of inflammatory conditions.

  通式I的化合物如下：##STR1## 其中：R.sub.1和R.sub.2分别是氢，C.sub.1-6烷基或一起是一个X基团，该基团是C.sub.3-6多亚甲基，其中一个碳原子可以被O，S或NR.sub.6取代，其中R.sub.6是氢或C.sub.1-6烷基; R.sub.3是一个单环或融合的双环杂芳基团，在芳环中最多有十个原子，其中不超过四个选择自氮、氧或硫，可选择地被一个或多个取代基C取代，所述取代基选择自卤素、CF.sub.3、硝基、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6硫基、C.sub.2-7脂肪酰基或氰基; 或是苯基或萘基，可选择地被一个或多个取代基选择自卤素、CF.sub.3、硝基、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6硫基、C.sub.2-7脂肪酰基、羧基、C.sub.1-6烷氧羰基、氰基、CONR.sub.7R.sub.8，其中R.sub.7和R.sub.8选择自氢或C.sub.1-6烷基或一起是一个X基团；NR.sub.9R.sub.10，其中R.sub.9和R.sub.10选择自氢、C.sub.1-6烷基、C.sub.2-7脂肪酰基或C.sub.1-6烷基磺酰基或一起是一个X基团；SO.sub.2NR.sub.11R.sub.12，其中R.sub.11和R.sub.12选择自氢或C.sub.1-6烷基或一起是一个X基团；或S(O).sub.mR.sub.13，其中m为1或2，R.sub.13为C.sub.1-6烷基；Z为萘基或一个单环或融合的双环杂芳香环，在芳环中最多有十个原子，其中不超过四个选择自氮、氧或硫，或（当R.sub.3为如上所定义的可选择取代的萘基或杂芳基团）Z为苯环；并且Z可选择地被一个或两个取代基R.sub.4和R.sub.5取代，所述取代基独立选择自C.sub.1-6烷基、氰基、氨基、氨基羰基或氨基羰酰基，可选择地被一个或两个C.sub.1-6烷基基团或一个X基团取代，卤素、CF.sub.3、硝基、C.sub.1-6烷氧基、C.sub.1-6硫基、C.sub.2-7脂肪酰氧基或羟基，或在相邻碳原子上一起是亚甲二氧基或C.sub.3-5多亚甲基。这些化合物作为治疗炎症状况的活性治疗物质被揭示。
• Dihydroisoquinoline derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0183369A2

  公开（公告）日：1986-06-04

  Compounds of the general formula I in which: R, and R2 are independently hydrogen, C, 6 alkyl ortogether are a group X which is C3 6 polymethylene optionally in which one carbon atom is replaced by O, S or NR6 wherein R6 is hydrogen or C1 6 alkyl; R3 is a mono- or fused bi-cyclic heteroaromatic group having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur, optionally C-substituted by one or more substituents selected from halogen, CF3, nitro, C1-6 alkoxy, C1-6 alkylthio, C2-7 alkanoyl or cyano; or is phenyl or naphthyl, optionally substituted by one or more substituents selected from halogen, CF3, nitro, C1-6 alkyl, C1 6 alkoxy, C1 6 alkylthio, C2-7 alkanoyl, carboxyl, C1-6 alkoxycarbonyl, cyano, CONR7R8 wherein R7 and R8 are selected from hydrogen or C1-6 alkyl or together are a group X; NR9 R10 wherein R9 and R10 are selected from hydrogen, C1-6 alkyl, C2-7 alkanoyl or C1-6 alkylsulphonyl or together are a group X; SO2NR11R12 wherein R11 and R12 are selected from hydrogen or C1-6 alkyl or together are a group X; or S(O)mR13 wherein m is 1 or 2 and R13 is C1-6 alkyl; Z is naphthyl or a mono- or fused bycyclic heteroaromatic ring having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur or (when R3 is an optionally substituted naphthyl or heteroaromatic group as defined) Z is a phyenyl ring; and Z is optionally C-substituted by one or two substituents R4 and R5 which are independently selected from C1-6 alkyl, cyano, amino, aminocarbonyl or aminocarbamoyl optionally substituted by one or two C1-6 alkyl groups or by a group X, halogen, CF3, nitro, C1-6 alkoxy, C1-6 alkylthio, C2-7 alkanoyloxy or hydroxy, or together on adjacent carbon atoms are methylenedioxy or C3-5 polymethylene, are disclosed as an active therapeutic substances for the treatment of inflammatory conditions.

  通式 I 的化合物 其中 R 和 R2 独立地为氢、C, 6 烷基或共同为基团 X，该基团为 C3 6 聚亚甲基，其中一个碳原子可选地被 O、S 或 NR6 取代，其中 R6 为氢或 C1 6 烷基； R3 是单环或融合双环杂芳香族基团，在芳香环中最多有 10 个原子，其中不超过 4 个原子选自氮、氧或硫，可选择被一个或多个选自卤素、CF3、硝基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰基或氰基的取代基取代；或苯基或萘基，任选被一个或多个选自卤素、CF3、硝基、C1-6 烷基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰基、羧基、C1-6 烷氧羰基、氰基的取代基取代； CONR7R8 其中 R7 和 R8 选自氢或 C1-6 烷基，或共同组成基团 X；NR9 R10，其中 R9 和 R10 选自氢、C1-6 烷基、C2-7 烷酰基或 C1-6 烷基磺酰基，或两者同为一个基团 X； SO2NR11R12，其中 R11 和 R12 选自氢或 C1-6 烷基，或两者同为一个基团 X；或 S(O)mR13 其中 m 为 1 或 2，R13 为 C1-6 烷基； Z 为萘基或单环或融合环状杂芳香族环，其芳香环中最多有 10 个原子，其中不超过 4 个原子选自氮、氧或硫，或（当 R3 为任选取代的萘基或定义的杂芳香族基团时）Z 为茚基环；Z任选被一个或两个取代基 R4 和 R5 取代，这两个取代基独立地选自 C1-6 烷基、氰基、氨基、氨基羰基或氨基甲酰基，任选被一个或两个 C1-6 烷基或基团 X、卤素、CF3、硝基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰氧基或羟基取代，或在相邻碳原子上一起被亚甲基二氧基或 C3-5 聚亚甲基取代。
• MCCARTHY, J. R.;WRIGHT, D. L.;SCHUSTER, A. J.;ABDALLAH, ABDUL, H.;SHEA, P+, J. MED. CHEM., 1985, 28, N 11, 1721-1727
  作者：MCCARTHY, J. R.、WRIGHT, D. L.、SCHUSTER, A. J.、ABDALLAH, ABDUL, H.、SHEA, P+

  DOI：——

  日期：——