ethyl N-(3-butenyl)carbamate | 5041-32-7

• 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: ethyl N-(3-butenyl)carbamate
• 英文别名: ethyl 3-butenylcarbamate；N-Buten-3-yl-carbaminsaeure-aethylester；1-Carbethoxyamino-buten-(3)；(N-Buten-3-yl-1-)-urethan；Ethyl but-3-en-1-ylcarbamate；ethyl N-but-3-enylcarbamate
• CAS: 5041-32-7
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: UUDCIVJTMZEFPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  ethyl N-(3-butenyl)carbamate 在 吡啶 、 4-二甲氨基吡啶 、 四氯化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 23.0h， 生成 trans-4-chloro-1,2-piperidinedicarboxylic acid 1-ethyl, 2-methyl ester
  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
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 生成 ethyl N-(3-butenyl)carbamate
  参考文献：
  名称：

  Levchenko,E.S. et al., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1838 - 1842

  摘要：

  DOI：

文献信息

• Stereoselectivity of 6-<i>Exo</i> Cyclization of α-Carbamoyl Radicals
  作者：Liyan Song、Xinqiang Fang、Zijia Wang、Kun Liu、Chaozhong Li

  DOI：10.1021/acs.joc.6b00008

  日期：2016.3.18

  stereoselectivity in the 6-exo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. The BEt3/O2-initiated iodine-atom-transfer radical cyclization reactions of substituted N-(but-3-en-1-yl)-N-(tert-butyl)-2-iodoalkanamides were carried out, which led to the predominant formations of 3,4-cis, 4,5-trans, or 4,6-trans substituted δ-lactams. Density functional calculations at the

  实验和理论上研究了α-氨基甲酰基自由基在6 - exo环化中的立体选择性。进行了由BEt 3 / O 2引发的取代的N-（but-3-en-1-yl）-N-（叔丁基）-2-碘代烷酰胺的碘原子转移自由基环化反应，导致3,4-顺式，4,5-反式或4,6-反式取代的δ-内酰胺的主要形成。在B3LYP / 6-31G *级别的密度泛函计算表明，6- exo自由基环化通过船构构过渡态进行。此外，提供了对立体选择性的机械见解，计算结果与实验观察结果非常吻合。
• Synthesis of Functionally Substituted Alkylboronic Acids. Hydroboration of N-Alkenylureas and -carbamates¹
  作者：D. N. Butler、A. H. Soloway

  DOI：10.1021/ja00955a019

  日期：1966.2
• Formic acid-induced π-cyclization of glycine cation equivalents to substituted pipecolic acid derivatives
  作者：Peter M Esch、de Boer F Richard、Hiemstra Henk、Ilona M Boska、Speckamp W. Nico

  DOI：10.1016/s0040-4020(01)86444-9

  日期：1991.1

  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.
• 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：——
• PELKIS N. P.; SLYUSARENKO E. I.; LEVCHENKO E. S., ZH. ORGAN. XIMII, 1979, 15, HO 1, 103-105
  作者：PELKIS N. P.、 SLYUSARENKO E. I.、 LEVCHENKO E. S.

  DOI：——

  日期：——