N-(phenylthioacetyl)pyrrolidine | 425618-70-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(phenylthioacetyl)pyrrolidine
• 英文别名: [(Phenylthio)acetyl]pyrrolidine；2-phenylsulfanyl-1-pyrrolidin-1-ylethanone
• CAS: 425618-70-8
• 化学式: C₁₂H₁₅NOS
• mdl: MFCD02636333
• 分子量: 221.323
• InChiKey: PEHILLCDALOINM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(phenylthioacetyl)pyrrolidine 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.33h， 以95%的产率得到N-(phenylsulfonylacetyl)pyrrolidine
  参考文献：
  名称：

  New versions of Pd0-catalyzed allylation of C-nucleophiles

  摘要：

  针对 Pd0 催化的 C 核亲和剂烯丙基化提出了新的 "一锅式 "方案，包括用原位生成的二烷基酰胺和烷氧基阴离子对相应的 CH 酸进行去质子化。

  DOI：

  10.1007/s11172-006-0555-x
• 作为产物：
  描述：

  苯硫基乙酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(phenylthioacetyl)pyrrolidine
  参考文献：
  名称：

  2,4-二取代丁内酯的立体选择性合成

  摘要：

  基于取代的 N-(pent-4-enoyl) 吡咯烷的反式立体选择性亲电环化制备了一系列 2,4-二取代丁醇内酯。丁醇内酯可被视为此类天然产物的合成子。

  DOI：

  10.1007/s11172-007-0021-4

文献信息

• Direct access to α-sulfenylated amides/esters <i>via</i> sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters
  作者：Yi Jiang、Jie-dan Deng、Hui-hong Wang、Jiao-xia Zou、Yong-qiang Wang、Jin-hong Chen、Long-qing Zhu、Hong-hua Zhang、Xue Peng、Zhen Wang

  DOI：10.1039/c7cc09026a

  日期：——

  An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred

  在氧气气氛下，已经开发出一种高效，环境友好的和前所未有的合成各种α-亚磺酰化酰胺/酯的方法。该反应显示出良好的官能团耐受性和优异的化学/区域选择性。即使在克规模上，也以中等至极好的收率获得了所有所需的产品。实际上，相关的α-硫醇Weinreb酰胺可以很容易地转移到一系列预期的化合物中，并且硒原子可以高产率地引入到酰胺的α-位。
• Development of Chiral Ureates as Chiral Strong Brønsted Base Catalysts
  作者：Azusa Kondoh、Sho Ishikawa、Masahiro Terada

  DOI：10.1021/jacs.9b13922

  日期：2020.2.26

  Recently, chiral Brønsted bases having high basicity have emerged as a powerful tool in developing new catalytic enantioselective reactions. However, such chiral strong Brønsted base catalysts are still very scarce. Herein, we report the development of a chiral anionic Brønsted base having a N,N'-dialkyl ureate moiety as a basic site. Its prominent catalytic activity was demonstrated in the enantioselective

  最近，具有高碱度的手性 Brønsted 碱已成为开发新的催化对映选择性反应的有力工具。然而，这种手性强的布朗斯台德碱催化剂仍然非常稀缺。在此，我们报告了具有 N,N'-二烷基脲酸酯部分作为碱性位点的手性阴离子 Brønsted 碱的开发。α-硫代乙酰胺作为酸性较低的亲核试剂与各种亲电子试剂的对映选择性加成反应证明了其突出的催化活性。因此，新开发的具有高可及性和结构可调性的手性催化剂将扩大布朗斯特碱催化下可行的对映选择性转化的范围。
• Allylation of prochiral C-nucleophiles catalyzed by the Pd(0)—(S)-(—)-BINAP complex
  作者：A. V. Lozanova、T. M. Ugurchieva、V. V. Veselovsky

  DOI：10.1007/s11172-008-0239-9

  日期：2008.8

  The allylation of prochiral C-nucleophiles catalyzed by the Pd(0)—(S)-(—)-BINAP complex (BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) was studied. The enantioselectivity of the allylation was found to be low.

  研究了 Pd(0)-(S)-(-)-BINAP 复合物（BINAP 是 2,2′-双（二苯基膦）-1,1′-联萘）催化的亲手性 C 核亲和剂的烯丙基化。发现烯丙基化的对映选择性较低。
• The reactivity of N,N-dialkyl-N-(3-phenylsulfinyltetrahydrofuran-2-ylidene)ammonium bromide
  作者：T. M. Ugurchieva、A. V. Lozanova、M. V. Zlokazov、V. V. Veselovsky

  DOI：10.1007/s11172-007-0240-8

  日期：2007.8

  amide under the action of bromine afforded (3R*,5S*, SS*)-N-(5-bromomethyl-3-phenylsulfinyltetrahydrofuran-2-ylidene)-N,N-diisopropylammonium bromide. Its transformations under the conditions of hydrolysis, dehydrobromination, and hydride reduction were studied.

  摘要 (2R*,SS*)-N, N-diisopropyl-2-phenylsulfinylpent-4-enamide 在溴作用下反式立体选择性亲电环化得到 (3R*,5S*, SS*)-N-(5-bromomethyl -3-苯基亚磺酰基四氢呋喃-2-亚基)-N,N-二异丙基溴化铵。研究了其在水解、脱溴化氢和氢化物还原条件下的转化。
• Homolytic Bond Dissociation Enthalpies of the Acidic H-A Bonds Caused by Proximate Substituents in Sets of Methyl Ketones, Carboxylic Esters, and Carboxamides Related to Changes in Ground State Energies
  作者：F. G. Bordwell、Shizhong Zhang、Xian-Man Zhang、Wei-Zhong Liu

  DOI：10.1021/ja00132a008

  日期：1995.7

  Equilibrium acidities in DMSO were measured for the N-H bonds in 15 carboxamides, and the homolytic bond dissociation enthalpies (BDEs) for these bonds were estimated. For the N-H bonds in five aliphatic carboxamides, the average PKHA is 25.5 and the average BDE is 108 +/- 2 kcal/mol. Equilibrium acidities in DMSO of the C-H bonds for seven sets of acids in series of the type GCH(2)COCH(3), GCH(2)CO(2)Et, and GCH(2)CONR(2) and the oxidation potentials of their conjugate bases, E(ox)(A(-)), where G is H, Ph, PhS, 1,3-dithianyl, Me(3)N(+), Ph(3)P(+), or MeCO, are also reported. For every set, there is a progressive increase in PKHA and a smaller progressive cathodic shift of E(ox)(A(-)), which are associated with progressive small increases in the BDEs of the acidic C-H bonds. These increases in BDEs are believed to be associated with progressive decreases in ground state energies in the order ketone > ester > amide. These results conform to a general rule that structural changes in weak acids that decrease ground state energies will tend to increase the BDEs of acidic H-A bonds, and vice versa.