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氯甲氧基甲基环丙烷 | 105688-12-8

中文名称
氯甲氧基甲基环丙烷
中文别名
——
英文名称
chloromethyl cyclopropylmethyl ether
英文别名
[(Chloromethoxy)methyl]cyclopropane;chloromethoxymethylcyclopropane
氯甲氧基甲基环丙烷化学式
CAS
105688-12-8
化学式
C5H9ClO
mdl
MFCD19233093
分子量
120.579
InChiKey
FNEOQFSJCPCUJX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    131.0±13.0 °C(Predicted)
  • 密度:
    1?+-.0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.5
  • 重原子数:
    7
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    9.2
  • 氢给体数:
    0
  • 氢受体数:
    1

SDS

SDS:b05a0fafefd7a42e5b9049a0d8c5c46c
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反应信息

  • 作为反应物:
    参考文献:
    名称:
    Nonnucleoside HIV-1 Reverse-Transcriptase Inhibitors, Part 5. Synthesis and Anti-HIV-1 Activity of Novel 6-Naphthylthio HEPT Analogues
    摘要:
    作为发现新的 HIV 逆转录酶抑制剂的一系列研究的一部分,合成了各种新型 6α- 和 6β- 萘硫基 1-[(2-羟乙氧基)甲基]-6-(苯硫基)胸腺嘧啶(HEPT)衍生物,并对其体外抗 HIV-1 活性进行了评估。结果表明,大多数 6α-naphthylthio HEPT 衍生物(7a-w)都表现出良好的活性[7e 的 IC50 值为 0.048 μM,选择性指数(SI)值为 735;7h 的 IC50 值为 0.057 μM,选择性指数(SI)值为 579;7k 的 IC50 值为 0.063 μM,选择性指数(SI)值为 0.063 μM,SI 值为 565],6β-萘硫基 HEPT 衍生物(8a-f)的活性较低,但在 6β-萘硫基系列(11a-c)的 6β-萘环的 C-1 位上引入 α 硝基后,抗 HIV-1 活性显著提高。
    DOI:
    10.1248/cpb.53.886
  • 作为产物:
    描述:
    Methoxymethoxymethyl-cyclopropane三氯化硼 作用下, 以 正己烷正戊烷 为溶剂, 以66%的产率得到氯甲氧基甲基环丙烷
    参考文献:
    名称:
    Cleavage of methoxymethyl ethers with boron trichloride. A convenient, versatile preparation of chloromethyl ether derivatives
    摘要:
    DOI:
    10.1021/jo00374a040
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文献信息

  • Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1-(alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium halides for reactivation of organophosphorus-inhibited acetylcholinesterases
    作者:Clifford D. Bedford、Ralph N. Harris、Robert A. Howd、Dane A. Goff、Gary A. Koolpe、M. Petesch、Alexi Miller、Harold W. Nolen、H. A. Musallam
    DOI:10.1021/jm00122a034
    日期:1989.2
    A series of structurally related mono- and bis-1,3-disubstituted 2-[(hydroxyimino)methyl]imidazolium halides were evaluated in vitro for their ability to reactivate electric eel, bovine, and human erythrocyte (RBC) acetylcholinesterases (AChE) inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP) and 3,3-dimethyl-2-butyl methyl-phosphonofluoridate (soman, GD). All new compounds were characterized for (hydroxyimino)methyl acid dissociation constant, nucleophilicity, octanol-buffer partition coefficient, reversible AChE inhibition, and kinetics of reactivation of EPMP-inhibited AChEs. For GD-inhibited AChEs, maximal reactivation was used to compare compounds since rapid phosphonyl enzyme dealkylation "aging" complicated interpretation of kinetic constants. For comparison, we also evaluated three known pyridinium therapeutics, 2-PAM, HI-6, and toxogonin. In vivo evaluation in mice revealed that when selected imidazolium compounds were coadministered with atropine sulfate, they were effective in providing lifesaving protection against both GD and EPMP challenges. This was a major accomplishment in the search for effective anticholinesterase therapeutics--the synthesis and preliminary evaluation of the first new monoquaternary soman antidotes with potencies superior to 2-PAM. Significantly, there was an apparent inverse relationship between in vitro and in vivo results; the most potent in vivo compounds proved to be the poorest in vitro reactivators. These results suggested that an alternative and possibly novel antidotal mechanism of protective action may be applicable for the imidazolium aldoximes. Selected compounds were also evaluated for their inhibition of AChE phosphorylation by GD and antimuscarinic and antinicotinic receptor blocking effects.
  • GOFF D. A.; HARRIS R. N., III; BOTTARO J. C.; BEDFORD C. D., J. ORG. CHEM., 51,(1986) N 24, 4711-4714
    作者:GOFF D. A.、 HARRIS R. N., III、 BOTTARO J. C.、 BEDFORD C. D.
    DOI:——
    日期:——
  • ——
    作者:TOMIOKA XIROKI、 YANO TOSIXIKO、 TAKEHDA XISAKI、 XIRATA NAONORI
    DOI:——
    日期:——
  • 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
  • Nonnucleoside HIV-1 Reverse-Transcriptase Inhibitors, Part 5. Synthesis and Anti-HIV-1 Activity of Novel 6-Naphthylthio HEPT Analogues
    作者:Guang-Fu Sun、Xu-Xiang Chen、Fen-Er Chen、Yue-Ping Wang、Erik De Clercq、Jan Balzarini、Christophe Pannecouque
    DOI:10.1248/cpb.53.886
    日期:——
    As part of a series of studies to discover new HIV reverse-transcriptase inhibitors, various novel 6α- and 6β-naphthylthio 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) derivatives were synthesized, and in vitro anti-HIV-1 activity was evaluated. The results revealed that most of 6α-naphthylthio HEPT derivatives (7a—w) showed good activity [for 7e, IC50 value of 0.048 μM and selectivity index (SI) value of 735; for 7h, IC50 value of 0.057 μM and SI value of 579; for 7k, IC50 value of 0.063 μM and SI value of 565], 6β-naphthylthio HEPT derivatives (8a—f) showed low activity, but the introduction of α nitro group to the C-1 position of the 6β-naphthyl ring in the 6β-naphthylthio series (11a—c) resulted in a dramatic increase in anti-HIV-1 activity.
    作为发现新的 HIV 逆转录酶抑制剂的一系列研究的一部分,合成了各种新型 6α- 和 6β- 萘硫基 1-[(2-羟乙氧基)甲基]-6-(苯硫基)胸腺嘧啶(HEPT)衍生物,并对其体外抗 HIV-1 活性进行了评估。结果表明,大多数 6α-naphthylthio HEPT 衍生物(7a-w)都表现出良好的活性[7e 的 IC50 值为 0.048 μM,选择性指数(SI)值为 735;7h 的 IC50 值为 0.057 μM,选择性指数(SI)值为 579;7k 的 IC50 值为 0.063 μM,选择性指数(SI)值为 0.063 μM,SI 值为 565],6β-萘硫基 HEPT 衍生物(8a-f)的活性较低,但在 6β-萘硫基系列(11a-c)的 6β-萘环的 C-1 位上引入 α 硝基后,抗 HIV-1 活性显著提高。
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