2-甲基-2-丙基2H-吖丙因-3-羧酸酯 | 215181-17-2

• 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
• 中文名称: 2-甲基-2-丙基2H-吖丙因-3-羧酸酯
• 英文名称: t-butyl 2H-azirine 3-carboxylate
• 英文别名: tert-butyl 2H-azirine-3-carboxylate
• CAS: 215181-17-2
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: ATIZUBVHCAPGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基2H-吖丙因-3-羧酸酯 在 4-二甲氨基吡啶 、 Dimethylzinc 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 192.83h， 生成
  参考文献：
  名称：

  Enantioselective Diels–Alder Cycloadditions in the Synthesis of Two Enantiomeric Sets of Chiral Polyhydroxylated Pipecolic Acid Derivatives

  摘要：

  （2E）-五烯-2,4-二烯-1-醇通过使用路易斯酸催化的自组装Diels-Alder方法与亲电的叔丁基2H-叠氮-3-甲酸盐结合，其中1,1-双萘酚-2,2-二醇（BINOL）作为手性诱导剂。通过改变BINOL诱导剂的手性，可以以高对映选择性和产率获得环加成产物的两种对映体形式。环加成产物的简单化学转化给出了两种类型的多羟基哌啶酸。这一合成策略首次报道了链分支哌啶酸的合成。

  DOI：

  10.1055/s-0034-1378227
• 作为产物：
  描述：

  tert-butyl 2,3-dibromopropanoate 在 sodium azide 作用下， 以 正庚烷 为溶剂， 反应 173.0h， 生成 2-甲基-2-丙基2H-吖丙因-3-羧酸酯
  参考文献：
  名称：

  Generation and Diels-Alder reactions of t-butyl 2H-azirine-3-carboxylate

  摘要：

  The azirinyl ester 2 (R = Bu-t) has been generated by thermolysis of t-butyl 2-azidoacrylate. It is too unstable to allow its full characterisation but it has been intercepted by Diels-Alder cycloaddition to several dienes. Addition to a chiral diene 8 is highly diastereoselective. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01617-7

文献信息

• Catalytic Enantioselective Reaction of 2<i>H</i>-Azirines with Thiols Using Cinchona Alkaloid Sulfonamide Catalysts
  作者：Shuichi Nakamura、Daiki Hayama、Masataka Miura、Tsubasa Hatanaka、Yasuhiro Funahashi

  DOI：10.1021/acs.orglett.7b04022

  日期：2018.2.2

  The first catalytic enantioselective reaction of 2H-azirines with thiols has been developed. The obtained aziridines can be converted to optically active oxazolines, aziridylamides, or α-sulfonyl esters. Transformation of these optically active aziridines showed that 2H-azirines act as β,β-dicarbocationic amine synthons.

  已经开发出2 H-叠氮基与硫醇的第一催化对映选择性反应。所获得的氮丙啶可以转化为光学活性的恶唑啉，叠氮基酰胺或α-磺酰基酯。这些旋光性氮丙啶的转化表明，2 H-氮丙啶可作为β，β-二碳并氨基胺合成子。
• Novel aziridine esters by the addition of aromatic nitrogen heterocycles to a 2H-azirine-3-carboxylic ester
  作者：Maria José Alves、Paula M.T Ferreira、Hernâni L.S Maia、Luı́s S Monteiro、Thomas L Gilchrist

  DOI：10.1016/s0040-4039(00)00755-3

  日期：2000.6

  Methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxoylate acts as an efficient alkylating agent for a variety of five-membered aromatic heterocycles. The aziridines derived from heterocycles that bear an alpha-carbonyl substituent react with TFA to give pyrroloimidazoles; 2,6-dichlorobenzaldehyde is also produced. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric Diels–Alder cycloadditions of d-erythrose 1,3-butadienes to achiral t-butyl 2H-azirine 3-carboxylate
  作者：Vera C.M. Duarte、Hélio Faustino、Maria J. Alves、António Gil Fortes、Nuno Micaelo

  DOI：10.1016/j.tetasy.2013.05.015

  日期：2013.9

  Two D-erythrose 1,3-butadienes were reacted with electrophilic achiral t-butyl 2H-azirine 3-carboxylate giving cycloadducts with good yields and moderate selectivity. The isomers could be separated to give the major (R)-isomers at C-2 in approximately 50% yield in both cases. Alternatively LACASA-DA methodology was applied to one of the reactions leading to homochiral (R)- and (S)-products by changing the chiral nature of an extra chiral BINOL inductor used. (C) 2013 Elsevier Ltd. All rights reserved.