tert-butyl (S)-2-[(benzylmethyl)carbamoyl]pyrrolidine-1-carboxylate | 170233-12-2

• 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
• 英文名称: tert-butyl (S)-2-[(benzylmethyl)carbamoyl]pyrrolidine-1-carboxylate
• 英文别名: (S)-tert-butyl 2-(benzyl(methyl)carbamoyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-[benzyl(methyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 170233-12-2
• 化学式: C₁₈H₂₆N₂O₃
• 分子量: 318.416
• InChiKey: INAGOMYFRPSFPP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-[(benzylmethyl)carbamoyl]pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S)-N-benzyl-N-methylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid

  摘要：

  New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinylmethyl)amine in the presence of dichloroacetic acid.

  DOI：

  10.3987/com-08-s(f)86
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.83h， 生成 tert-butyl (S)-2-[(benzylmethyl)carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  羧酸到酰胺的简单一锅法转化

  摘要：

  摘要 在 CH3CN 中使用对硝基苯磺酰氯、Et3N 和 DMAP 将羧酸原位转化为羧酸-（对硝基苯）磺酸酐，与伯胺或仲胺反应，以高产率得到酰胺。

  DOI：

  10.1080/00397919508011836

文献信息

• Regioselective Benzoylation of 6-O-Protected and 4,6-O-Diprotected Hexopyranosides as Promoted by Chiral and Achiral Ditertiary 1,2-Diamines
  作者：Guixian Hu、Andrea Vasella

  DOI：10.1002/hlca.200290018

  日期：2002.12

  Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at −60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends mostly on the structure of the alcohols; it is modulated by the configuration and constitution of the diamines, as shown by comparing the effect of Oriyama's

  三醇（6- Monobenzoylation ö -silylated glycopyranosides）或二醇（4,6- ö在-60℃至23 -benzylidenated glycopyranosides）与苯甲酰氯和三乙胺°通过催化量的二叔1,2-二胺的促进。区域选择性主要取决于醇的结构。通过比较Oriyama催化剂（（S）-1和（R）-1），N，N，N ′，N′-四甲基乙二胺（TMEDA ）的作用可以看出，它受二胺的构型和组成的调节。），N，N，N'，N'-四乙基乙二胺（TEEDA），Et 3 N和EtNMe 2。催化剂的空间位阻会削弱其对反应性的影响。与在Oriyama催化剂存在下外消旋-环己烷-1,2-二醇的单和二苯甲酰基化的适度对映选择性相一致，这些二胺对区域选择性的影响相当有限。尽管与过程简单相关，但是在某些情况下，这些催化剂比单一方法可产生更高的单种苯甲酸酯收率。在制备3-
• Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst
  作者：Rémi Andres、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202201788

  日期：2022.5.2

  A simple prolinamide bearing a single H-bond donor urea function catalyzes the Pictet–Spengler reaction between tryptamines and α-ketoamides to afford 1,1-disubstituted tetrahydro-β-carbolines in excellent yields and enantiomeric excesses.

  带有单一氢键供体尿素功能的简单脯氨酰胺可催化色胺和 α-酮酰胺之间的 Pictet-Spengler 反应，以优异的产率和对映体过量提供 1,1-二取代的四氢-β-咔啉。
• A Facile One-Pot Transformation of Carboxylic Acids to Amides
  作者：Jong Chan Lee、Yoon Hwan Cho、Hyeok Koo Lee、Sung Hye Cho

  DOI：10.1080/00397919508011836

  日期：1995.9

  Abstract Carboxylic acids, converted in situ into carboxylic-(p-nitrobenzene)sulfonic anhydrides using p-nitrobenzenesulfonyl chloride, Et3N, and DMAP in CH3CN, react with primary or secondary amines, to give amides in high yields.

  摘要 在 CH3CN 中使用对硝基苯磺酰氯、Et3N 和 DMAP 将羧酸原位转化为羧酸-（对硝基苯）磺酸酐，与伯胺或仲胺反应，以高产率得到酰胺。
• A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid
  作者：Kohei Inomata、Yuichi Akahane、Yasuyuki Endo

  DOI：10.3987/com-08-s(f)86

  日期：——

  New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinylmethyl)amine in the presence of dichloroacetic acid.