N-(1-buten-3-yl)formamide | 64222-02-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-buten-3-yl)formamide
• 英文别名: N-but-3-en-2-ylformamide
• CAS: 64222-02-2
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: UFSYJXKNHBJMHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  75-77 °C(Press: 1 Torr)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-buten-3-yl)formamide 在 2,2'-联吡啶 、 copper(l) chloride lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams

  摘要：

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.

  DOI：

  10.1021/jo00054a034
• 作为产物：
  描述：

  丁-3-烯-2-胺 以 甲酸甲酯 为溶剂， 生成 N-(1-buten-3-yl)formamide
  参考文献：
  名称：

  Substituted N-methylene derivatives of thienamycin

  摘要：

  披露了替代的噻氨霉素N-亚甲基衍生物，可以用以下结构式表示：##STR1##其中X和Y从氢、R、OR、SR和NR.sup.1 R.sup.2组成的群中选择，其中R是取代或未取代的：烷基、烯基、炔基、环烷基、环烷基烷基、芳基、芳基烷基、杂芳基、杂芳基烷基、杂环烷基和杂环烷基烷基；R.sup.1和R.sup.2是氢或R。这些化合物及其药学上可接受的盐、醚、酯和酰胺衍生物可用作抗生素。还披露了制备这些化合物的方法；包括这些化合物的药物组合物；以及在需要抗生素效果时，施用这些化合物和组合物的治疗方法。

  公开号：

  US04194047A1

文献信息

• Substituted N-methylene derivatives of thienamycin
  申请人：Merck & Co., Inc.

  公开号：US04194047A1

  公开（公告）日：1980-03-18

  Disclosed are substituted N-methylene derivatives of thienamycin which may be represented by the following structural formula: ##STR1## wherein X and Y are selected from the group consisting of hydrogen, R, OR, SR, and NR.sup.1 R.sup.2 wherein, inter alia, R is substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R.sup.1 and R.sup.2 are hydrogen or R. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  披露了替代的噻氨霉素N-亚甲基衍生物，可以用以下结构式表示：##STR1##其中X和Y从氢、R、OR、SR和NR.sup.1 R.sup.2组成的群中选择，其中R是取代或未取代的：烷基、烯基、炔基、环烷基、环烷基烷基、芳基、芳基烷基、杂芳基、杂芳基烷基、杂环烷基和杂环烷基烷基；R.sup.1和R.sup.2是氢或R。这些化合物及其药学上可接受的盐、醚、酯和酰胺衍生物可用作抗生素。还披露了制备这些化合物的方法；包括这些化合物的药物组合物；以及在需要抗生素效果时，施用这些化合物和组合物的治疗方法。
• Studies on vinyl isocyanides
  作者：R.B. King、L. Borodinsky

  DOI：10.1016/s0040-4020(01)96674-8

  日期：1985.1

  spectra of the vinyl isocyanides, but not their molybdenum carbonyl complexes, indicate coupling of the isocyanide nitrogen to both the isocyanide carbon (1J(C-N)6 Hz. ) and the vinyl carbon bearing the isocyanide group (1J(C-N)11-13 Hz. ) leading to 1:1:1 triplets for these resonances. These vinyl carbonyl resonances are used to estimate the cis-trans isomer ratios in vinyl isocyanides of the type RCHCHNC

  乙烯基异腈2,4,6-（CH 3）3 c ^ 6 ħ 2 CHCHNC和（CH 3）3 CCHCHNC和新-1,3-二烯基胩CH 3 CHCH（CH 3）-CH SchCHNC是使用Schöllkopf，Stafforst和Jentsch首先开发的方法，由相应的醛和甲基异氰化物制备的。5个新的乙烯基异氰化物（CH 3）2 CCHNC和CH 3 CHC（CH 3）NC已经制备通过将Cu 2相应的烯丙基异氰酸酯的O催化异构化液态乙烯基异氰酸酯的特征在于，在室温下与降冰片二烯四羰基钼在己烷溶液中反应，可以形成固体顺式（RNC）2 Mo（CO）4衍生物。通过质子和碳13 NMR光谱对这些钼羰基络合物的检查表明，乙烯基1异氰酸酯配体的异氰化物碳原子但不与碳原子键合到钼原子上。乙烯基异氰化物的质子去耦碳13 NMR光谱，但未显示羰基钼络合物，表明异氰酸酯氮既与异氰酸酯碳（1 J（CN）6H
• KING, R. B.;BORODINSKY, L., TETRAHEDRON, 1985, 41, N 16, 3235-3240
  作者：KING, R. B.、BORODINSKY, L.

  DOI：——

  日期：——
• Substituted N-methylene derivatives of thienamycin sulfoxide and sulfone
  申请人：Merck & Co., Inc.

  公开号：US04232030A1

  公开（公告）日：1980-11-04

  Disclosed are substituted N-methylene derivatives of thienamycin sulfoxide (I, n=1) and sulfone (I, n=2) which may be represented by the following structural formula: ##STR1## wherein X and Y are selected from the group consisting of hydrogen, R, OR, SR, and NR.sup.1 R.sup.2 wherein, inter alia, R is substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R.sup.1 and R.sup.2 are hydrogen or R. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  揭示了替代的噻氨酸亚氧化物（I，n=1）和砜（I，n=2）的N-亚甲基衍生物，可以用以下结构式表示：##STR1## 其中X和Y从氢，R，OR，SR和NR.sup.1 R.sup.2组成的群体中选择，其中，R是取代或未取代的：烷基，烯基，炔基，环烷基，环烷基烷基，芳基，芳基烷基，杂芳基，杂芳基烷基，杂环烷基和杂环烷基烷基；R.sup.1和R.sup.2是氢或R。这些化合物及其药学上可接受的盐，醚，酯和酰胺衍生物可用作抗生素。还揭示了制备这些化合物的方法；包含这些化合物的药物组合物；以及在需要抗生素效果时，施用这些化合物和组合物的治疗方法。
• Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams
  作者：Hideo Nagashima、Nobuyasu Ozaki、Masayuki Ishii、Koji Seki、Masayoshi Washiyama、Kenji Itoh

  DOI：10.1021/jo00054a034

  日期：1993.1

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.