(1-methoxy-[2]naphthyl)-acetonitrile | 71056-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-methoxy-[2]naphthyl)-acetonitrile
• 英文别名: Methoxynaphthalene-2-yl Acetonitrile；1-Methoxynaphthalene-2-acetonitrile；2-(1-methoxynaphthalen-2-yl)acetonitrile
• CAS: 71056-95-6
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: SQYNWGFXHYGXRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-methoxy-[2]naphthyl)-acetonitrile 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.92h， 生成 4-[(1-methoxy-2-naphthalenyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide
  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
• 作为产物：
  描述：

  1-甲氧基-2-萘甲酸 在 氯化亚砜 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 37.67h， 生成 (1-methoxy-[2]naphthyl)-acetonitrile
  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

• 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。
• Approaches to anthracyclines. 1. Conjugate aroylation of .alpha.,.beta.-unsaturated esters
  作者：Kathlyn A. Parker、James Kallmerten

  DOI：10.1021/jo01301a015

  日期：1980.6
• Chatterjea, Journal of the Indian Chemical Society, 1959, vol. 36, p. 76,80
  作者：Chatterjea

  DOI：——

  日期：——
• MCCARTHY J. R.; MOORE J. L.; CREGGE R. J., TETRAHEDRON LETT., 1978, NO 52, 5183-5186
  作者：MCCARTHY J. R.、 MOORE J. L.、 CREGGE R. J.

  DOI：——

  日期：——
• Cyanohydrin ethers and esters as high-sensitivity enzyme substrates
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20030207344A1

  公开（公告）日：2003-11-06

  Ethers and esters of cyanohydrins that contain optically detectable moieties are highly effective for detecting, monitoring, and measuring the activity of enzymes that cause the cleavage of certain types of substrates. The cyanohydrins function as proaldehydes and proketones, spontaneously converting to aldehydes and ketones, respectively, which provide a large increase in optical detectability relative to both the starting esters and ethers and the cyanohydrins.