methyl 3-(E)-hexenylcarbamate | 135690-91-4

• 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: methyl 3-(E)-hexenylcarbamate
• 英文别名: methyl N-<(E)-3-hexenyl>carbamate；methyl N-(3-(E)-hexenyl)carbamate；methyl N-[(E)-hex-3-enyl]carbamate
• CAS: 135690-91-4
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: ZINPVNUCEGSHDB-SNAWJCMRSA-N

物化性质

• 沸点：
  234.8±19.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(E)-hexenylcarbamate 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 3-(1-formyloxypropyl)-1-pyrrolidinecarboxylic acid methyl ester
  参考文献：
  名称：

  Formic acid-induced π-cyclization of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Formic acid-mediated cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)-acetoxyglycine esters are described. The major reaction products are 4-formyloxypipecolic acid derivatives, formed with low stereoselectivity at C-4. The several subtle features of the cyclization process are satisfactorily explained by a mechanism involving (1) a rapid cationic aza-Cope rearrangement of the incipient iminium ion and (2) participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86444-9
• 作为产物：
  描述：

  反式-3-己烯-1-醇 在 sodium azide 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.75h， 生成 methyl 3-(E)-hexenylcarbamate
  参考文献：
  名称：

  Tin tetrachloride-induced π-cyclizations of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Cationic pi-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described. Reactions started and quenched with water at -78-degrees-C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products. A mechanistic scheme is advanced which adequately explains these results. The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86443-7

文献信息

• Copper catalyzed chlorine transfer cyclizations of glycine and glycolic acid derivatives
  作者：Jan H. Udding、Henk Hiemstra、Marco N.A. van Zanden、W.Nico Speckamp

  DOI：10.1016/0040-4039(91)80706-c

  日期：1991.6

  Chloroglycine and chloroglycolic acid derivatives smoothly cyclize in the presence of a catalytic amount of cuprous chloride and 2,2′-bipyridine to produce functionalized proline and 2-tetrahydrofurancarboxylic esters, respectively, in an atom transfer process.

  在催化量的氯化亚铜和2,2'-联吡啶的存在下，氯甘氨酸和氯乙醇酸衍生物可在原子转移过程中平稳环化，分别生成官能化的脯氨酸酯和2-四氢呋喃羧酸酯。
• ESCH, PETER M.;HIEMSTRA, HENK;SPECKAMP, W. NICO, TETRAHEDRON LETT., 31,(1990) N, C. 759-762
  作者：ESCH, PETER M.、HIEMSTRA, HENK、SPECKAMP, W. NICO

  DOI：——

  日期：——