(1-phenylpent-4-enyl)carbamic acid tert-butyl ester | 861882-42-0

• 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: (1-phenylpent-4-enyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl 1-phenylpent-4-enylcarbamate；tert-butyl N-(1-phenylpent-4-en-1-yl)carbamate；tert-butyl N-(1-phenylpent-4-enyl)carbamate
• CAS: 861882-42-0
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: HVZLJKADFDAGAU-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  375.6±31.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (1-phenylpent-4-enyl)carbamic acid tert-butyl ester 在 palladium diacetate potassium phosphate 、 lithium aluminium tetrahydride 、 DPE-Phos 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 (+/-)-(2RS,5SR)-4-(1-methyl-5-phenylpyrrolidin-2-ylmethyl)phenylmethanol
  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：

  1-苯基-4-戊烯-1-酮 在 乙酸铵 、 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 19.0h， 生成 (1-phenylpent-4-enyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  的立体选择性合成Ñ通过γ-的Pd-催化的反应（ -保护的吡咯烷ñ -酰基）烯烃和γ-（Ñ -Boc -氨基）链烯与芳基溴化物

  摘要：

  描述了通过Pd催化的γ-（N-酰基氨基）烯烃和γ-（N -Boc-氨基）烯烃与芳基溴的立体反应合成的N-酰基和N - Boc保护的吡咯烷。这些反应在一次操作中实现两个键的形成，并且通常以高水平的非对映选择性进行。与先前描述的γ-（N-芳基氨基）烯烃反应相反，这些转化反应在富电子和缺电子的芳基溴化物以及乙烯基溴化物底物下均以高收率和高区域选择性进行。

  DOI：

  10.1016/j.tet.2005.03.110

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。
• (E)-Dimethyl 2-Oxopent-3-enylphosphonate: An Excellent Substrate for Cross-Metathesis - Easy Access to Functionalized Heterocycles
  作者：Thomas Cochet、Didier Roche、Véronique Bellosta、Janine Cossy

  DOI：10.1002/ejoc.201101398

  日期：2012.2

  Simple and efficient access to tetrahydrofurans, tetrahydropyrans, and pyrrolidines through a tandem cross-metathesis/1,4-addition process from (E)-dimethyl 2-oxopent-3-enylphosphonate and N-protected ω-unsaturated amines or alcohols under microwave irradiation is described. As the Grubbs–Hoveyda catalyst is highly chemoselective, a diversity of functionalized heterocycles were synthesized. Furthermore

  在微波辐射下，通过 (E)-2-氧代戊-3-烯基膦酸二甲酯和 N-保护的 ω-不饱和胺或醇通过串联交叉复分解/1,4-加成过程简单有效地获得四氢呋喃、四氢吡喃和吡咯烷被描述。由于 Grubbs-Hoveyda 催化剂具有高度化学选择性，因此合成了多种功能化杂环。此外，由于存在在杂环的 C2 位置具有酮膦酸酯的侧链，因此可以进行额外的官能化。
• Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes
  作者：Stefano Nicolai、Raha Sedigh-Zadeh、Jérôme Waser

  DOI：10.1021/jo400254q

  日期：2013.4.19

  Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this context oxy- and aminoalkynylation are especially important reactions because of the numerous transformations possible with the triple bond of acetylenes yet these methods have been limited to the use of silyl protected acetylenes. Herein we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.
• Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines
  作者：Stefano Nicolai、Jérôme Waser

  DOI：10.1021/ol2029383

  日期：2011.12.2

  The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of acetylenes is further exploited to access key building blocks for the synthesis of bioactive natural products.
• Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas
  作者：Yasuhiro Nishikawa、Seikou Kimura、Yuri Kato、Natsuka Yamazaki、Osamu Hara

  DOI：10.1021/ol5037453

  日期：2015.2.20

  A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)(2)/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.