chloromethyl 3-phenylprop-2(E)-en-1-yl ether | 117983-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: chloromethyl 3-phenylprop-2(E)-en-1-yl ether
• 英文别名: [(E)-3-chloromethoxy-1-propenyl]benzene；[(E)-3-(chloromethoxy)prop-1-enyl]benzene
• CAS: 117983-70-7
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: LEQDEUZETIEVHG-QPJJXVBHSA-N

物化性质

• 沸点：
  289.4±28.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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 3-phenylprop-2(E)-en-1-yl ether 在 4,4'-二叔丁基苯并 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到2-苯基丁-3-烯-1-醇
  参考文献：
  名称：

  [2,3]-通过氯-锂交换进行的维蒂希重排

  摘要：

  不同的烯丙基氯甲基醚1与过量的锂粉（摩尔比为1：7）和催化量的DTBB（2.5 mol％）在THF中的反应在0°C下反应1 h，在用水水解后，得到预期的[2,3] -Wittig重排产生的唯一醇2。如对苄基氯甲基醚所举例说明的，相同的方法也可用于相应的[1,2]-维蒂希重排。

  DOI：

  10.1016/j.tetlet.2005.06.160
• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 三氯化硼 、 sodium hydride 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 2.0h， 生成 chloromethyl 3-phenylprop-2(E)-en-1-yl 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

• 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
• 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：——
• [2,3]-Wittig rearrangement by a chlorine–lithium exchange
  作者：Beatriz Maciá、Cecilia Gómez、Miguel Yus

  DOI：10.1016/j.tetlet.2005.06.160

  日期：2005.9

  reaction of different allylic chloromethyl ethers 1 with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (2.5 mol %) in THF at 0 °C for 1 h gives, after hydrolysis with water, the expected alcohols 2 resulting from a [2,3]-Wittig rearrangement, in an exclusive manner. The same process can also be applied to the corresponding [1,2]-Wittig rearrangement, as it is exemplified

  不同的烯丙基氯甲基醚1与过量的锂粉（摩尔比为1：7）和催化量的DTBB（2.5 mol％）在THF中的反应在0°C下反应1 h，在用水水解后，得到预期的[2,3] -Wittig重排产生的唯一醇2。如对苄基氯甲基醚所举例说明的，相同的方法也可用于相应的[1,2]-维蒂希重排。
• 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
  作者：Clifford D. Bedford、Ralph N. Harris、Robert A. Howd、Dane A. Goff、Gary A. Koolpe、M. Petesch、Irwin Koplovitz、Walter E. Sultan、H. A. Musallam

  DOI：10.1021/jm00122a035

  日期：1989.2

  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.