1-(chloromethoxy)-3-methylbut-2-ene | 117983-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(chloromethoxy)-3-methylbut-2-ene
• CAS: 117983-50-3
• 化学式: C₆H₁₁ClO
• mdl: MFCD19235739
• 分子量: 134.606
• InChiKey: LSMZQXYLQLDZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  1-(chloromethoxy)-3-methylbut-2-ene 在 甲醇 、 platinum(IV) oxide 、 sodium tetrahydroborate 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 46.5h， 生成
  参考文献：
  名称：

  通过应变光级联中间体简明全合成 Agarozizanol B

  摘要：

  从简单的茚满酮衍生物开始，在光化学级联中形成非对映体纯的中间体1 ，并作为琼脂齐嗪醇 B ( 2 ) 的前体，在拆分步骤后作为外消旋体或单一对映体。

  DOI：

  10.1002/anie.202110009
• 作为产物：
  描述：

  异戊烯醇 在 三氯化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 mineral oil 、 正戊烷 为溶剂， 反应 32.0h， 生成 1-(chloromethoxy)-3-methylbut-2-ene
  参考文献：
  名称：

  通过应变光级联中间体简明全合成 Agarozizanol B

  摘要：

  从简单的茚满酮衍生物开始，在光化学级联中形成非对映体纯的中间体1 ，并作为琼脂齐嗪醇 B ( 2 ) 的前体，在拆分步骤后作为外消旋体或单一对映体。

  DOI：

  10.1002/anie.202110009

文献信息

• 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.
• Total Synthesis of (+)-Prezizaan-15-ol, (+)-Jinkohol II, and (+)-Jinkoholic Acid
  作者：Niklas Rauscher、Christian Jandl、Thorsten Bach

  DOI：10.1021/acs.orglett.3c01184

  日期：2023.6.16

  into (+)-prezizaan-15-ol. The major diastereoisomer with a 2α-Me configuration gave in an analogous route (+)-jinkohol II, which was oxidized at C13 to (+)-jinkoholic acid. A previous ambiguity regarding the configuration of the natural products could be clarified by total synthesis.
• Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate
  作者：Niklas Rauscher、Line Næsborg、Christian Jandl、Thorsten Bach

  DOI：10.1002/anie.202110009

  日期：2021.11.2

  Starting from a simple indanone derivative, diastereomerically pure intermediate 1 was formed in a photochemical cascade and served as precursor to agarozizanol B (2), either as racemate or as single enantiomer after a resolution step.

  从简单的茚满酮衍生物开始，在光化学级联中形成非对映体纯的中间体1 ，并作为琼脂齐嗪醇 B ( 2 ) 的前体，在拆分步骤后作为外消旋体或单一对映体。