N-[2-(cyclopent-2-enylethyl)]amine | 857353-42-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[2-(cyclopent-2-enylethyl)]amine
• 英文别名: 2-(cyclopent-2-en-1-yl)ethan-1-amine；2-(cyclopent-2-en-1-yl)ethanamine；2-(cyclopent-2-enyl)ethylamine；3-<2-Amino-aethyl>-cyclopenten-(1)；2-(cyclo-2-penten-1-yl)ethylamine；2-cyclopent-2-en-1-ylethanamine
• CAS: 857353-42-5
• 化学式: C₇H₁₃N
• 分子量: 111.187
• InChiKey: MBTOTUHFSJWIIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[2-(cyclopent-2-enylethyl)]amine 在 tris(dibenzylideneacetone)dipalladium (0) 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 、 2-二苯基磷-2'-(N,N-二甲氨基)联苯 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[b]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction

  摘要：

  The Pd/phosphine-catalyzed reaction of 1 with aryl bromides leads to the selective synthesis of either 6-aryl octahydrocyclopenta[b]pyrroles (3), the corresponding 5-aryl isomers 5, diarylamine 2, or hexahydrocyclopenta[b]pyrrole 4 depending on the structure of the phosphine ligand. These transformations are effective with a variety of different aryl bromides and provide 3-5 with excellent levels of diastereo-selectivity (dr >= 20:1). The changes in product distribution are believed to derive from the influence of Pd-catalyst structure on the relative rates of reductive elimination, beta-hydride elimination, alkene insertion, and alkene displacement processes in a mechanistically complex reaction. The effect of phosphine ligand structure on product distribution is described in detail, along with analysis of a proposed mechanism for these transformations.

  DOI：

  10.1021/ja0430346
• 作为产物：
  描述：

  环戊-1-烯-1-乙酸 生成 N-[2-(cyclopent-2-enylethyl)]amine
  参考文献：
  名称：

  Method for inhibition of HIV related viruses

  摘要：

  揭示了治疗艾滋病、抑制HIV及相关病毒复制以及使用硫脲衍生物化合物或其盐的配方。还揭示了新型硫脲衍生物化合物。

  公开号：

  US05593993A1

文献信息

• Palladium‐Catalyzed C−H Alkynylation of Unactivated Alkenes
  作者：Benedikt S. Schreib、Marlene Fadel、Erick M. Carreira

  DOI：10.1002/anie.202000935

  日期：2020.5.11

  Palladium-catalyzed regio- and diastereoselective C-H functionalization with bromoalkynes and electronically unbiased olefins is reported. The picolinamide directing group enables the formation of putative 5 and 6-exo-metallacycles as intermediates to afford monoalkynylated products in up to 91 % yield in a stereospecific fashion. The systematic study reveals that substrates with a wide range of substituents

  报道了用溴代炔烃和电子无偏烯烃对钯催化的区域和非对映选择性CH官能化。吡啶甲酰胺引导基团能够形成假定的5和6-外金属环化合物作为中间体，以立体特异性方式提供高达91％收率的单炔基化产物。系统的研究表明，在烯烃和溴代炔烃偶合配偶体上具有广泛取代基的底物是可以接受的。证明了所获得的酰胺，烯烃和炔烃的化学选择性转化。
• Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer
  作者：Qilei Zhu、David E. Graff、Robert R. Knowles

  DOI：10.1021/jacs.7b11144

  日期：2018.1.17

  Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiol hydrogen atom donor. Reaction outcomes are consistent with the intermediacy

  在这里，我们报告了一种使用初级和次级磺酰胺对未活化烯烃进行分子间抗马尔科夫尼科夫加氢胺化的催化方法。这些反应在室温下在可见光照射下发生，并由铱 (III) 光催化剂、磷酸二烷基酯碱和硫醇氢原子供体共同催化。反应结果与通过磺酰胺 NH 键的质子耦合电子转移激活产生的 N 中心磺酰胺自由基的中间体一致。概述了反应的合成范围（> 60 个例子）和机械特征的研究。
• Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides
  作者：Myra Beaudoin Bertrand、John P. Wolfe

  DOI：10.1016/j.tet.2005.03.110

  日期：2005.6

  stereoselective synthesis of N-acyl- and N-Boc-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides is described. These reactions effect formation of two bonds in a single operation and proceed with generally high levels of diastereoselectivity. In contrast to previously described reactions of γ-(N-arylamino) alkenes, these transformations

  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。
• Palladium-Catalyzed Stereoselective Aza-Wacker–Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles
  作者：Rong-Shiow Tang、Li-Yuan Chen、Chin-Hung Lai、Ta-Hsien Chuang

  DOI：10.1021/acs.orglett.0c03552

  日期：2020.12.4

  Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically

  进行了钯催化的分子内串联环化反应，以合成致密的顺式/顺式稠合的氮杂四环结构。该过程涉及钯（II）催化的好氧aza-Wacker反应，然后是钯（0）催化的Heck反应。系统地研究了溶剂和苯的取代方式对一锅两步级联反应的影响，并提出了可能的机理。使用钯催化的aza-Wacker-Heck环化反应，也可以快速合成应变的五氢苯并[ f ]环戊基[ hi ]吲哚并嗪-6-和外消旋的γ-二十烷。
• Pleuromutilin derivatives for use in the treatment of diseases mediated by microbes
  申请人：Nabriva Therapeutics AG

  公开号：EP2433926A1

  公开（公告）日：2012-03-28

  Compounds selected from the group ofN-unsubstituted or N-alkylated or N-acylated 14-O-[(amino(C0-4)alkyl-hydroxy-cycloalkyl- or bicycloalkylsulfanyl)-acetyl]-mutilins which are 14-O-[(amino(C0-4)alkyl-hydroxy-cyclobutylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy-cyclopentylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy-cycloheptylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy-cyclooctylsulfanyl)-acetyl]-mutilins, or 14-O-[(amino(C0-4)alkyt-hydroxy-bicycloalkylsulfanyl)-acetyl]-mutilins, optionally in the form of a salt and/or a solvate, a pharmaceutical compositions comprising such compounds and their use as pharmaceuticals, e.g. for the treatment of microbial infections and for the treatment of acne, optionally in combination with other pharmaceutically active agents.

  从N-未取代或N-烷基化或N-酰化的14-O-[(氨基(C0-4)烷基-羟基-环烷基或双环烷基硫醚基)-乙酰基]-螺旋霉素中选择的化合物，其为14-O-[(氨基(C0-4)烷基-羟基-环丁基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环戊基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环庚基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环辛基硫醚基)-乙酰基]-螺旋霉素，或14-O-[(氨基(C0-4)烷基-羟基-双环烷基硫醚基)-乙酰基]-螺旋霉素，可选地以盐和/或溶剂的形式存在，包括这些化合物的药物组合物以及它们作为药物的用途，例如用于治疗微生物感染和痤疮的治疗，可选地与其他药用活性剂联合使用。