甲基1-烯丙基-2-吖丁啶羧酸酯 | 205443-20-5

• 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: 甲基1-烯丙基-2-吖丁啶羧酸酯
• 英文名称: N-allylazetidine-2-carboxylate
• 英文别名: methyl N-allylazetidine-2-carboxylate；1-(2-Propenyl)-2-azetidinecarboxylic acid methyl ester；methyl 1-prop-2-enylazetidine-2-carboxylate
• CAS: 205443-20-5
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ILMKVRDGJKJHDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基1-烯丙基-2-吖丁啶羧酸酯 在 ammonium hydroxide 作用下， 反应 3.0h， 生成 (+/-)-1-allylazetidine-2-carboxamide
  参考文献：
  名称：

  Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

  摘要：

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00632-0
• 作为产物：
  描述：

  2,4-二溴丁酸甲酯 、 丙烯胺 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以64%的产率得到甲基1-烯丙基-2-吖丁啶羧酸酯
  参考文献：
  名称：

  Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

  摘要：

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00632-0

文献信息

• Polycyclic Ring Formation Using Bis-diazolactams for Cascade Stitching
  作者：Sara A. Bonderoff、Albert Padwa

  DOI：10.1021/acs.joc.6b02663

  日期：2017.1.6

  3-sigmatropic rearrangement, as well as nitrogen ylide formation followed by azetidine ring expansion. The initial reaction can be paired with a subsequent tandem cascade sequence involving dipole formation/cycloaddition in either an intra- or intermolecular sense to generate polycyclic N-heterocycles in one pot, with the formation up to three new rings in a single operation. Excellent diastereoselectivity

  使用3-重氮-1-（乙基2-二氮杂烯酰基）吲哚-2-酮在铑（+）下检测同一分子中供体/受体（D / A）和受体/受体（A / A）重氮基团的化学选择性反应。 II）催化。优先形成衍生自D / A重氮基团的金属类金属化合物，并进行选择性的CH，NH和OH插入反应，环丙烷化，环丙烷化，形成硫叶立德/ 2,3-σ重排以及形成氮叶立德，然后形成氮杂环丁烷环膨胀。初始反应可以与随后的串联级联序列配对，所述串联级联序列在分子内或分子间意义上涉及偶极形成/环加成，以生成多环N-在一个锅中杂环，一次操作最多可形成三个新的环。在分子内环加成反应中观察到极好的非对映选择性，产生5至7元环。
• One-Carbon Ring Expansion of Azetidines via Ammonium Ylide [1,2]-Shifts: A Simple Route to Substituted Pyrrolidines
  作者：Tina M. Bott、John A. Vanecko、F. G. West

  DOI：10.1021/jo9001323

  日期：2009.4.3

  diazocarbonyl compounds in the presence of catalytic Cu(acac)2 to furnish substituted pyrrolidines via Stevens [1,2]-shift. In all but two examples, complete selectivity was seen for ring expansion rather than migration of the other exocyclic group on the azetidinium nitrogen. The two exceptions, observed with ylides substituted with two carbonyl groups and lacking a stabilizing group at the 2-position

  在催化性Cu（acac）2存在下，将简单的N-取代的氮杂环丁烷与重氮羰基化合物一起加热，以通过Stevens [1,2]-位移提供取代的吡咯烷。除了两个实例以外，在氮杂环丁烷氮上，对于环的扩张而不是其他外环基团的迁移，都具有完全的选择性。对于两个被两个羰基取代且在氮杂环丁烷2位上缺乏稳定基团的烷基化物所观察到的两个例外，它们经历了环外苄基迁移，优先于环的扩展。
• Enzyme preparation and method of using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20030124683A1

  公开（公告）日：2003-07-03

  There is disclosed are an enzyme preparation characterized by a polymer carrier having fine pores with average radius of 200-500 Å and the enzyme is capable of converting an N-substituted cyclic imino ester into an (S)—N-substituted cyclic imino acid, thereby an (S)—N-substituted cyclic imino acid is preferentially produced, and has an amino acid sequence as set forth in SEQ ID NO: 1 or the like.

  本发明公开了一种酶制剂，其特征在于具有平均半径为200-500Å的细孔的聚合物载体，并且该酶能够将N-取代的环状亚氨酸酯转化为（S）-N-取代的环状亚氨酸，从而优先产生（S）-N-取代的环状亚氨酸，并具有SEQ ID NO:1或类似的氨基酸序列。
• Esterase genes and uses of the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1057894A2

  公开（公告）日：2000-12-06

  The present invention provides a novel gene encoding a protein having an excellent catalyst ability for producing (S)-N-substituted cyclic imino acid represented by the general formula (2) (= the (S)-cyclic imino acid (2)): and to provide a novel method for producing the (S)-cyclic imino acid (2) by an asymmetric hydrolization of the N-substituted cyclic imino acid ester represented by the general formula (1): in a manner of gene engineering technology utilizing the novel gene provided.

  本发明提供了一种新型基因，该基因编码的蛋白质在生产通式(2)代表的(S)-N-取代环 亚胺酸(=(S)-环亚胺酸(2))方面具有优异的催化能力： 并提供一种通过通式(1)代表的 N-取代环亚胺酸酯的不对称水解生产 (S)-环亚胺酸(2)的新方法： 以基因工程技术的方式利用所提供的新型基因。
• Esterace genes and uses of the same
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20020173013A1

  公开（公告）日：2002-11-21

  The present invention provides a novel gene encoding a protein having an excellent catalyst ability for producing (S)-N-substituted cyclic imino acid represented by the general formula (2) (=the (S)-cyclic imino acid (2)): 1 and to provide a novel method for producing the (S)-cyclic imino acid (2) by an asymmetric hydrolization of the N-substituted cyclic imino acid ester represented by the general formula (1): 2 in a manner of gene engineering technology utilizing the novel gene provided.

  本发明提供了一种新型基因，该基因编码的蛋白质在生产通式(2)代表的(S)-N-取代环亚胺酸(&等于;(S)-环亚胺酸(2))方面具有优异的催化能力： 1 并提供一种通过通式(1)代表的 N-取代环亚胺酸酯的不对称水解生产(S)-环亚胺酸(2)的新方法： 2 以基因工程技术的方式利用所提供的新型基因。