N-(2-丙炔基)琥珀酰亚胺 | 10478-33-8

• 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
• 中文名称: N-(2-丙炔基)琥珀酰亚胺
• 中文别名: N-炔丙基琥珀酰亚胺
• 英文名称: 1-(prop-2-yn-1-yl)pyrrolidine-2,5-dione
• 英文别名: 1-(prop-2-ynyl)pyrrolidine-2,5-dione；N-propargylsuccinimide；1-prop-2-ynylpyrrolidine-2,5-dione
• CAS: 10478-33-8
• 化学式: C₇H₇NO₂
• mdl: MFCD06740819
• 分子量: 137.138
• InChiKey: DOTAQRZGKATJIC-UHFFFAOYSA-N

物化性质

• 熔点：
  51.0 to 55.0 °C
• 沸点：
  237°C(lit.)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-丙炔基)琥珀酰亚胺 在 溴化氰 、 silver perchlorate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 24.0h， 生成 高氯酸[4-(2,5-二羰基吡咯烷-1-基)丁-2-炔-1-基](二甲基)锍
  参考文献：
  名称：

  Dimethylsulfonium and thiolanium analogs of the muscarinic agent oxotremorine

  摘要：

  Dimethylsulfonium (6a and 6b) and thiolanium analogues (7a and 7b) of oxotremorine were synthesized and found to be potent muscarinic agents in vivo and vitro. Compound 6a exceeded oxotremorine in potency. Their affinities for muscarinic receptors in the guinea pig ileum and urinary bladder, estimated pharmacologically, were higher than those of the corresponding trimethylammonium (8a and 8b) and N-methylpyrrolidinium compounds (9a and 9b). However, the new compounds had lower intrinsic efficacies than their quaternary ammonium analogues. The compounds also had high affinity for central muscarinic receptors as measured by displacement of specifically bound (-)-[3H]-N-methylscopolamine from homogenates of the rat cerebral cortex. Half-maximal occupation of cortical muscarinic receptors by 6a, 6b, 7a, and 7b was achieved at concentrations of 0.8, 5.4, 0.3, and 3.3 microM, respectively. The competition curves of 6a, 6b, and 7a were adequately described by a two-site binding equation. The ratio of low- and high-affinity dissociation constants agreed with relative efficacy estimated on the ileum. The thiolanium salt 7a was a fairly potent nicotinic agent on the frog rectus abdominis.

  DOI：

  10.1021/jm00396a025
• 作为产物：
  描述：

  1-(2-丙炔-1-基)-1H-吡咯-2,5-二酮 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以45%的产率得到N-(2-丙炔基)琥珀酰亚胺
  参考文献：
  名称：

  马来酰亚胺电化学还原中的化学和非对映选择性

  摘要：

  在烯烃，炔基和苄基的存在下，可以化学选择性地将环状酰亚胺（马来酰亚胺）电化学还原成琥珀酰亚胺。通过在连续流反应器中使用3D电极证明了系统的效率。将3,4-二甲基马来酰亚胺还原为相应的琥珀酰亚胺，其非对映异构体比例为3：2，这与氮取代基和电极表面积无关。通过使用DFT计算合理化了该过程的立体选择性，其中涉及通过双氢转移机制发生的半烯醇的酸催化互变异构。

  DOI：

  10.1002/cssc.201403184

文献信息

• A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes
  作者：Jiawang Liu、Carolin Schneider、Ji Yang、Zhihong Wei、Haijun Jiao、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202010768

  日期：2021.1.4

  3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α‐alkynyl‐α, β‐unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density‐functional

  描述了（不）对称 1,3-二炔的化学选择性、区域选择性和立体选择性单氢酰胺化。这种新型转化成功的关键是采用具有特定配体 Neolephos 的先进钯催化剂系统。这种合成有用的 α-炔基-α, β-不饱和酰胺的通用方法的合成价值通过几种结构复杂的分子和上市药物的多样化得到了展示。控制实验和密度泛函理论 (M06L-SMD) 计算也表明底物在控制不对称 1,3-二炔的区域选择性中发挥着关键作用。
• Stereocontrolled Formation of Epoxy Peroxide FunctionalityAppended to a Lactam Ring
  作者：Charles M. Marson、Afzal Khan、Rod A. Porter

  DOI：10.1021/jo001313f

  日期：2001.7.1

  The action of tert-butyl hydroperoxide and tin(IV) chloride upon allylic alcohols containing a lactam ring leads mainly to epoxy alkyl peroxides with high diastereoselection. Both the stereochemistry and the products formed are in marked contrast to the reactions of the analogous carbocyclic allylic alcohols with tert-butyl hydroperoxide-VO(acac)2.

  叔丁基氢过氧化物和氯化锡（IV）对含有内酰胺环的烯丙基醇的作用主要导致具有高非对映选择性的环氧烷基过氧化物。立体化学和形成的产物均与类似的碳环烯丙基醇与叔丁基氢过氧化物-VO（acac）2的反应形成鲜明对比。
• Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy
  作者：Zheng‐Guang Wu、Xiang‐Ji Liao、Li Yuan、Yi Wang、You‐Xuan Zheng、Jing‐Lin Zuo、Yi Pan

  DOI：10.1002/chem.202000252

  日期：2020.5.4

  Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI -catalyzed azide-alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate

  Click化学专注于使用简单的前体进行分子的精细合成的高选择性反应的开发。毋庸置疑，CuI催化的叠氮化物-炔烃环加成（CuAAC）是点击化学最有价值的例子之一，但由于需要额外的还原剂和配体以及细胞毒性铜，因此受到一些限制。在这里，我们展示了一种新颖的叠氮化物-炔烃环加成反应的策略，该策略涉及光氧化还原电子转移自由基机理，而不是传统的金属催化配位过程。这种新开发的光催化的叠氮化物-炔烃环加成反应可以在室温下，在空气和可见光存在的条件下，在温和条件下进行，显示出良好的官能团耐受性，优异的原子经济性，高达99％的高收率，和绝对的区域选择性，提供了各种1,4-二取代的1,2,3-三唑衍生物，包括生物活性分子和药物。使用可回收的光催化剂，太阳能和水作为溶剂，使该光催化系统具有可持续性和环境友好性。此外，叠氮化物-炔烃环加成反应可以在具有优异区域选择性的无金属催化剂的存在下进行光催化，这代表了点击化学
• Ligand‐Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β‐Unsaturated Thioesters
  作者：Han‐Jun Ai、Wangyang Lu、Xiao‐Feng Wu

  DOI：10.1002/anie.202106079

  日期：2021.7.26

  the synthesis of unsaturated thioesters. A robust ligand-controlled regioselective thiocarbonylation of alkynes is developed. Utilizing boronic acid and 5-chlorosalicylic acid as the acid additive to in situ form 5-chloroborosalicylic acid (5-Cl-BSA), and bis(2-diphenylphosphinophenyl)ether (DPEphos) as the ligand, linear α,β-unsaturated thioesters were produced in a straightforward manner. Switching

  炔烃的硫羰基化为合成不饱和硫酯提供了理想的方法。开发了一种强大的配体控制的炔烃区域选择性硫代羰基化。以硼酸和5-氯水杨酸为酸添加剂，原位生成5-氯硼水杨酸(5-Cl-BSA)，双(2-二苯基膦基苯基)醚(DPEphos)为配体的线性α,β-不饱和硫酯以直接的方式生产。将配体切换为三（2-呋喃基）膦可以改变反应选择性，得到支化产物。值得注意的是，这种方法也代表了内部炔烃的硫代羰基化的第一个例子。
• Triazolium Salts as Appropriate Catalytic Scaffolds for 1,4-Additions to α,β-Unsaturated Carbonyls
  作者：Ielyzaveta Bratko、Gregorio Guisado-Barrios、Isabelle Favier、Sonia Mallet-Ladeira、Emmanuelle Teuma、Eduardo Peris、Montserrat Gómez

  DOI：10.1002/ejoc.201301220

  日期：2014.4

  containing a rigid dihydroanthracenyl skeleton are suitable precursors for both organometallic and organo-based catalysts. A Rh–carbene complex and the triazolium salt efficiently catalyzed the 1,4-additions of C- and heterodonor reagents to α,β-unsaturated carbonyl substrates, respectively.

  含有刚性二氢蒽基骨架的 1,2,3-三唑衍生物是有机金属和有机基催化剂的合适前体。Rh-卡宾配合物和三唑鎓盐分别有效地催化 C-和杂供体试剂与 α,β-不饱和羰基底物的 1,4-加成反应。