methoxymethyl 2-methyl-2-propenyl ether | 90344-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxymethyl 2-methyl-2-propenyl ether
• 英文别名: 3-(methoxymethoxy)-2-methylprop-1-ene；3-Methoxymethoxy-2-methyl-1-propene
• CAS: 90344-72-2
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: SQJKHFQRGDUZTR-UHFFFAOYSA-N

物化性质

• 沸点：
  108-110 °C
• 密度：
  0.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methoxymethyl 2-methyl-2-propenyl ether 在 三氯化硼 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 1.0h， 以45%的产率得到chloromethyl 2-methyl-2-propen-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
• 作为产物：
  描述：

  氯甲基甲基醚 、 2-甲基-2-丙烯-1-醇 在 sodium hydride 作用下， 生成 methoxymethyl 2-methyl-2-propenyl ether
  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

文献信息

• The Nucleophilic 5<i>-endo-trig</i> Cyclization of 1,1<i>-</i>Difluoro-1-alkenes: Ring-Fluorinated Hetero- and Carbocycle Synthesis and Remarkable Effect of the Vinylic Fluorines on the Disfavored Process
  作者：Junji Ichikawa、Yukinori Wada、Masaki Fujiwara、Kotaro Sakoda

  DOI：10.1055/s-2002-33912

  日期：——

  The disfavored 5-endo-trig cyclizations have been accomplished for 1,1-difluoro-1-alkenes with nitrogen, oxygen, sulfur, and carbon nucleophiles by taking advantage of the properties of fluorine. β,β-Difluorostyrenes bearing tosylamido, hydroxy, or methylsulfinyl group at the o-position undergo intramolecular nucleophilic substitution with a loss of the vinylic fluorine, leading to 2-fluorinated indole, benzo[b]furan, and benzo[b]thiophene in high yields. 1,1-Difluoro-1-butenes bearing homoallylic tosyl­amido, hydroxy, mercapto, or iodomethyl group also successfully cyclize via a 5-endo-trig process with the in situ generated intramolecular nucleophiles to afford 2-fluoro-2-pyrroline, 5-fluoro-2,3-dihydrofuran, 5-fluoro-2,3-dihydrothiophene, and 1-fluorocyclo-pentene. The two vinylic fluorines proved to be essential and play a critical role in these ‘anti-Baldwin’ cyclizations.

  利用氟的特性，1,1-二氟-1-烯与氮、氧、硫和碳等亲核物进行了不受欢迎的 5-endo-trig 环化反应。o-位上带有对甲苯磺酰胺基、羟基或甲基亚磺酰基的δ²,δ²-二氟苯乙烯在失去乙烯基氟的情况下发生分子内亲核取代反应，从而高产出 2-氟化吲哚、苯并[b]呋喃和苯并[b]噻吩。含有同源烯丙基甲苯胺基、羟基、巯基或碘甲基的 1,1-二氟-1-丁烯也成功地与原位生成的分子内亲核物通过 5-endo-trig 过程发生环化反应，生成 2-氟-2-吡咯啉、5-氟-2,3-二氢呋喃、5-氟-2,3-二氢噻吩和 1-氟环戊烯。事实证明，在这些 "反鲍德温 "环化反应中，两个乙烯基氟是必不可少的，并发挥着关键作用。
• Olefin Carbometalation with (Alkoxy)allylic Lithium and Zinc Reagents. Four-Centered vs Six-Centered Mechanism of Allylmetalation Reaction
  作者：Katsumi Kubota、Seiji Mori、Masaharu Nakamura、Eiichi Nakamura

  DOI：10.1021/ja981634x

  日期：1998.12.1

  cyclopropenone acetal takes place smoothly to give carbometalation products of well-defined regio- and stereochemistry. The pathways of product formation depends on the metal. The (alkoxy)allylzinc reagents add to the cyclopropene in such a manner that the α-carbon attached to the alkoxy group becomes bound to the olefin. The regioselectivity of the (alkoxy)allylzincation is independent of the allyl substituents

  将取代的（烷氧基）烯丙基锂和锌试剂添加到环丙烯酮缩醛中可以顺利进行，得到具有明确区域和立体化学的碳金属化产物。产品形成的途径取决于金属。(烷氧基)烯丙基锌试剂以这样的方式加成至环丙烯，使得连接至烷氧基的α-碳与烯烃结合。（烷氧基）烯丙基锌阳离子的区域选择性与烯丙基取代基无关，新形成的碳 - 碳键的非对映选择性非常好（> 97％），并且产物中烯键的几何形状总是完全顺式（如果适用） ）。另一方面，（烷氧基）烯丙基锂化的区域选择性取决于取代基，而非对映选择性始终保持较高（> 97％）。
• Synthesis of proteasome inhibitor 6-deoxy-omuralide and its enantiomer using stereoselective alkylation of substituted proline ester
  作者：Feng Li、Volker Jäger

  DOI：10.1039/d0ob01053g

  日期：——

  A potent 20S proteasome inhibitor, 6-deoxy-omuralide was stereoselectively synthesized in 20 steps with 5.1% overall yield staring from a chiral boron agent and D-glyceraldehyde acetonide. The stereoselective alkylation of the substituted proline ester with 3-iodo-2-methylprop-1-ene served as the key step. The enantiomer of 6-deoxy-omuralide was achieved in 20 steps with 4.6% overall yield by just

  一种有效的20S蛋白酶体抑制剂6-脱氧-乌拉米利经20个步骤立体选择性地合成，总收率为5.1％，由手性硼剂和D-甘油醛丙酮化物引发。关键的步骤是用3-碘-2-甲基丙-1-烯进行取代的脯氨酸酯的立体选择性烷基化。通过在第一步中仅改变手性硼试剂，就可以在20个步骤中获得6-脱氧-乌拉米脲的对映体，总产率为4.6％。我们当前的工作为在C4位置装饰的6-脱氧-omuralide及其对映异构体提供了一种灵活的方法。
• 2,3-Dihydro-6-nitroimidazo[2,1-b]oxazoles
  申请人：Tsubouchi Hidetsugu

  公开号：US20060094767A1

  公开（公告）日：2006-05-04

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R 1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R 2 represents a group —OR 3 or the like, and R 3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R 1 and —(CH 2 ) n R 2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R 41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种2,3-二氢-6-硝基咪唑并[2,1-b]噁唑化合物，其通式如下：其中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R2代表—OR3或类似的基团，R3代表氢原子、C1-C6烷基或类似的基团，或者R1和—(CH2)nR2可以通过相邻的碳原子通过氮原子结合在一起形成一个螺环，其通式为（H）：其中，R41为氢、C1-C6烷基或类似的基团。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型酸性快速细菌具有优异的杀菌作用。
• 2,3-dihydro-6-nitroimidazo[2,1-b]oxazoles
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US07262212B2

  公开（公告）日：2007-08-28

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R2 represents a group —OR3 or the like, and R3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R1 and —(CH2)nR2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供一种由以下通式表示的2,3-二氢-6-硝基咪唑并[2,1-b]噁唑化合物：其中R1代表氢原子或C1-C6烷基，n代表0到6的整数，R2代表-OR3基团或类似基团，R3代表氢原子、C1-C6烷基或类似基团，或R1和-(CH2)nR2可以与相邻的碳原子通过氮原子结合在一起，形成由通式（H）表示的螺环：其中R41是氢、C1-C6烷基或类似基团。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型酸性快速菌具有优异的杀菌作用。