chloromethyl 1,1-dimethyl-2-propynyl ether | 55812-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chloromethyl 1,1-dimethyl-2-propynyl ether
• 英文别名: chloromethyl 2-methyl-3-butyn-2-yl ether；1,1-dimethyl-2-propynyloxymethyl chloride；Chlormethyl-1,1-dimethyl-2-propinylether；Chlormethyl-1,1-dimethyl-2-propynylether；3-(chloromethoxy)-3-methylbut-1-yne
• CAS: 55812-22-1
• 化学式: C₆H₉ClO
• mdl: MFCD19232250
• 分子量: 132.59
• InChiKey: HCKOFCYWVRQJQR-UHFFFAOYSA-N

物化性质

• 沸点：
  59-64 °C(Press: 70 Torr)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  chloromethyl 1,1-dimethyl-2-propynyl ether 、 1-methyl-1H-imidazole-2-carbaldehyde oxime 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到1-<<(1',1'-dimethyl-2'-propyn-1'-yl)oxy>methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication

  摘要：

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.

  DOI：

  10.1021/jm00122a035
• 作为产物：
  描述：

  3-甲氧基甲氧基-3-甲基-丁-1-炔 在 三氯化硼 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 1.0h， 以51%的产率得到chloromethyl 1,1-dimethyl-2-propynyl ether
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication

  摘要：

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.

  DOI：

  10.1021/jm00122a035

文献信息

• 1-Methoxy-1-methyl-3-{p-[(1,1-dimethyl-2-propynyloxy)-methoxy]phenyl}urea
  申请人：American Cyanamid Company

  公开号：US04046797A1

  公开（公告）日：1977-09-06

  This invention relates to novel (alkenyloxy), (alkynyloxy) and (cyanoalkoxy) alkoxyphenyl ureas and their use as herbicidal agents.

  这项发明涉及新颖的(烯烷氧基)、(炔烷氧基)和(氰基烷氧基)烷氧基苯基脲类化合物及其作为除草剂的用途。
• Novel (alkenyloxy)-, (alkynyloxy) and (cyanoalkoxy) alkoxyphenyl ureas
  申请人：American Cyanamid Company

  公开号：US04153448A1

  公开（公告）日：1979-05-08

  This invention relates to novel (alkenyloxy), (alkynyloxy) and (cyanoalkoxy) alkoxyphenyl ureas and their use as herbicidal agents.

  本发明涉及新型（烯丙氧基）、（炔丙氧基）和（氰基烷氧基）烷氧基苯基脲及其用作除草剂的用途。
• (Alkenyloxy)-, (alkynyloxy) and (cyanoalkoxy) alkoxyphenyl ureas and
  申请人：American Cyanamid Company

  公开号：US04046808A1

  公开（公告）日：1977-09-06

  This invention relates to novel (alkenyloxy), (alkynyloxy) and (cyanoalkoxy) alkoxyphenyl ureas and their use as herbicidal agents.

  本发明涉及新型的（烯烃氧基）、（炔烃氧基）和（氰基烷氧基）烷氧基苯基脲，以及它们作为除草剂的应用。
• Isothiazole derivatives containing (an) iodoalkylnyl group(s), their preparation and their use as fungicide and/or bactericide
  申请人：NIHON NOHYAKU CO., LTD.

  公开号：EP0697409A1

  公开（公告）日：1996-02-21

  An isothiazole derivative represented by the formula (I), wherein R¹ represents a hydrogen atom, C₁-C₆ alkyl, C₂-C₇ alkenyl, C₃-C₇ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ cyanoalkyl, C₁-C₆ haloalkyl, C₂-C₇ alkoxyalkyl, C₃-C₇ alkoxycarbonylalkyl, C₂-C₇ haloalkenyl, C₂-C₇ alkylcarbonyl, C₂-C₇ alkoxycarbonyl, iodoalkynyl, or iodoalkynyloxyalkyl group, R² represents a C₁-C₆ alkyl, C₂-C₇ alkenyl, C₃-C₇ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ cyanoalkyl, C₁-C₆ haloalkyl, C₂-C₇ alkoxyalkyl, C₃-C₇ alkoxycarbonylalkyl, C₂-C₇ haloalkenyl, C₂-C₇ alkylcarbonyl, C₂-C₇ alkoxycarbonyl, iodoalkynyl, or iodoalkynyloxyalkyl group, provided that at least one of R¹ and R² represents an iodoalkynyl or iodoalkynyloxyalkyl group, Y represents O or S, and Z represents O, S, SO, SO₂ or NR³ in which R³ represents a hydrogen atom, C₁-C₆ alkyl, C₂-C₇ alkenyl, C₃-C₇ alkynyl or benzyl group, or R³ and R², taken together, represent a C₃-C₅ alkylene group which may contain O or N, an agricultural, industrial and medical fungicides and/or bactericides containing said compound as an active ingredient.

  由式(I)代表的异噻唑衍生物、 其中 R¹ 代表氢原子、C₁-C₆烷基、C₂-C₇ 烯基、C₃-C₇ 炔基、C₃-C₇ 环烷基、C₁-C₆氰基烷基、C₁-C₆卤代烷基、C₂-C₇ 烷氧基烷基、C₃-C₇ 烷氧基羰基烷基、C₂-C₇ 卤代烯基、C₂-C₇ 烷基羰基、C₂-C₇ 烷氧基羰基、碘炔基或碘炔氧基烷基，R² 代表 C₁-C₆ 烷基、C₂-C₇ 烯基、C₃-C₇ 炔基、C₃-C₇ 环烷基、C₁-C₆氰基烷基、C₁-C₆卤代烷基、C₂-C₇ 烷氧基烷基、C₃-C₇烷氧羰基烷基、C₂-C₇卤代烯基、C₂-C₇烷基羰基、C₂-C₇烷氧基羰基、碘炔基或碘炔氧基烷基，条件是 R¹ 和 R² 中至少有一个代表碘炔基或碘炔氧基烷基，Y 代表 O 或 S、Z代表O、S、SO、SO₂或NR³，其中R³代表氢原子、C₁-C₆烷基、C₂-C₇烯基、C₃-C₇炔基或苄基，或R³和R²共同代表可含有O或N的C₃-C₅亚烷基、 含有上述化合物作为活性成分的农用、工业用和医用杀菌剂和/或杀菌剂。
• Cleavage of methoxymethyl ethers with boron trichloride. A convenient, versatile preparation of chloromethyl ether derivatives
  作者：Dane A. Goff、Ralph N. Harris、Jeffrey C. Bottaro、Clifford D. Bedford

  DOI：10.1021/jo00374a040

  日期：1986.11