3-methylpent-4-enylcarbamic acid benzyl ester | 928673-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methylpent-4-enylcarbamic acid benzyl ester
• 英文别名: benzyl N-(3-methylpent-4-en-1-yl)carbamate；benzyl N-(3-methylpent-4-enyl)carbamate
• CAS: 928673-82-9
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: GFKLBKCCMQMNGF-UHFFFAOYSA-N

物化性质

• 沸点：
  355.9±31.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylpent-4-enylcarbamic acid benzyl ester 在 palladium diacetate 盐酸 、 potassium phosphate 、 DPE-Phos 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 生成 (+/-)-(2RS,3SR)-2-(4-acetylbenzyl)-3-methylpyrrolidine
  参考文献：
  名称：

  Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions

  摘要：

  The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs2CO3 in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

  DOI：

  10.1021/ol062808f
• 作为产物：
  描述：

  3-甲基-4-戊烯酸 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 58.0h， 生成 3-methylpent-4-enylcarbamic acid benzyl ester
  参考文献：
  名称：

  Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions

  摘要：

  The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs2CO3 in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

  DOI：

  10.1021/ol062808f

文献信息

• Mild Conditions for Pd-Catalyzed Carboamination of <i>N</i>-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation
  作者：Myra Beaudoin Bertrand、Joshua D. Neukom、John P. Wolfe

  DOI：10.1021/jo801631v

  日期：2008.11.21

  with aryl bromides leads to greatly increased tolerance of functional groups and alkene substitution. Substrates derived from (E)- or (Z)-hex-4-enylamines are stereospecifically converted to 2,1'-disubstituted pyrrolidine products that result from suprafacial addition of the nitrogen atom and the aryl group across the alkene. Transformations of 4-substituted pent-4-enylamine derivatives proceed in high

  在N保护的γ-氨基烯烃与芳基溴化物的Pd催化碳氨化反应中使用弱碱Cs2CO3会导致官能团和烯烃取代的耐受性大大提高。衍生自（E）-或（Z）-己-4-烯基胺的底物被立体定向​​转化为2,1'-二取代的吡咯烷产物，该产物是通过在烯烃上表面氮原子和芳基的表面加成而产生的。以高收率进行4-取代的戊-4-烯胺衍生物的转化，得到2,2-二取代的产物，并且以高收率产生顺式-2,5-或反式-2,3-二取代的吡咯烷，并具有优异的非对映选择性。 -在C1或C3处带有取代基的被保护的戊-4-烯基胺。反应可耐受各种官能团，包括酯，硝基，和烯醇化的酮 详细说明了这些转换的范围和局限性，以及解释了所观察到的产物立体化学的模型。另外，还讨论了氘标记实验，该实验表明这些反应通过中间钯（芳基）（酰胺）配合物的顺氨基钯催化进行，而与烯烃的取代程度或反应条件无关。
• Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions
  作者：Myra Beaudoin Bertrand、Matthew L. Leathen、John P. Wolfe

  DOI：10.1021/ol062808f

  日期：2007.2.1

  The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs2CO3 in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.