methyl N-(R)-α-methylbenzylazetidine-2-carboxylate

• 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: methyl N-(R)-α-methylbenzylazetidine-2-carboxylate
• 英文别名: methyl N-[(R)-phenylethyl]azetidine-2-carboxylic acid；methyl N-[(R)-phenylethyl]azetidine-2-carboxylate；methyl 1-[(1R)-1-phenylethyl]azetidine-2-carboxylate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: FMYIXIBSKQXTLX-RWANSRKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  methyl N-(R)-α-methylbenzylazetidine-2-carboxylate 、 3-溴丙酸甲酯 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 methyl N-(R)-α-methylbenzyl-2-(3-methoxycarbonylethyl)azetidine-2-carboxylate 、 methyl N-(R)-α-methylbenzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate
  参考文献：
  名称：

  串联的分子内氮杂环丁烷开环/闭合级联反应合成螺环丙基γ-内酰胺：合成和机理方面

  摘要：

  报道了新颖的分子内氮杂环丁烷开环/闭合级联反应的范围和局限性，其从氮杂环丁烷以高区域和立体选择性提供螺环丙基γ-内酰胺。该方法的关键步骤是通过用TMSOTf和TEA处理产生的甲硅烷基烯酮缩醛使TMSOTf活化的氮杂环丁烷环S N 2型开环。这项研究是氮杂环丁烷亲核开环的非常罕见的例子，它不需要通过N-烷基化或使用N形成季铵盐-吸电子基团。该方法在2-氮杂环丁酮系统中的应用导致反应活性的完全改变，并通过空前的涉及酯受体和亚氨酸甲硅烷基酯的Mukaiyama aldol-like反应提供6-氮杂双环[3.2.0]庚烷衍生物。

  DOI：

  10.1016/j.tet.2012.03.111

文献信息

• 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。
• Method for racemization of optically active azetidine-2-carboxylate
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0957089A1

  公开（公告）日：1999-11-17

  A method for racemization of an optically active N-substituted azetidine-2-carboxylic acid ester of the formula (1): wherein * represents an asymmetric carbon atom, R1 represents an optionally substituted aryl group, a saturated hydrocarbon group which may be substituted with an optionally substituted aryl group, or an unsaturated hydrocarbon group, R2 represents a saturated hydrocarbon group which may be substituted, an optionally substituted unsaturated hydrocarbon group, an alkyloxycarbonyl group which may be substituted, an alkenyloxycarbonyl group, or an optionally substituted sulfonyl group,    which comprises heating the ester of the formula (1) at 100°C or higher or subjecting the ester to contact with a basic compound selected from an alkali metal hydride, an alkali metal alkoxide of a tertiary alcohol and an organic amine.

  一种式（1）的具有光学活性的 N-取代氮杂环丁烷-2-羧酸酯的消旋化方法： 其中 * 代表不对称碳原子、 R1 代表任选取代的芳基、可被任选取代的芳基取代的饱和烃基或不饱和烃基、 R2 代表可被取代的饱和烃基、可被取代的不饱和烃基、可被取代的烷氧羰基、烯氧羰基或可被取代的磺酰基、 其中包括在 100°C 或更高温度下加热式（1）的酯，或使酯与选自碱金属氢化物、叔醇的碱金属烷氧化物和有机胺的碱性化合物接触。
• 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。
• Preparation comprising an enzyme for asymmetrical hydrolysis of N-substituted C3-C4 cyclic imino-2-carboxylic acid ester and method of using the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1316610B1

  公开（公告）日：2006-05-03