trans-(3S,4S)-3-Methyl-4-ethylazetidin-2-one | 5303-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: trans-(3S,4S)-3-Methyl-4-ethylazetidin-2-one
• 英文别名: trans-3-Methyl-4-aethyl-azetidinon-(2)；2-Azetidinone, 4-ethyl-3-methyl-, trans-；(3S,4S)-4-ethyl-3-methylazetidin-2-one
• CAS: 5303-66-2
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: NZBAAVNEPKNXQN-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氨基戊酸 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 2-氯-1-甲基吡啶碘化物 、 对甲苯磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 39.5h， 生成 trans-(3S,4S)-3-Methyl-4-ethylazetidin-2-one
  参考文献：
  名称：

  Highly Diastereoselective Alkylation of Perhydropyrimidin-4-ones Directed toward the Synthesis of .alpha.-Substituted .beta.-Amino Acids. 2.

  摘要：

  The alkylation of several enantiomerically pure perhydropyrimidin-4-ones at C-5 is described. For the methylation reaction, mixtures of 5,6-trans- and cis-disubstituted adducts were obtained with high diastereomeric ratios, whereas only the 5,6-trans-disubstituted products were obtained with larger alkylating agents. The dialkylation reaction at C-5 was also studied, and the 5,6-cis-trisubstituted product was preferentially formed. Acidic,hydrolysis of 5,6-trans-disubstituted perhydropyrimidin-4-ones furnished the corresponding beta-amino acid hydrochlorides in quantitative yield. On cyclization of the amino acids, 5,6-trans-disubstituted azetidin-2-ones were also synthesized.

  DOI：

  10.1021/jo00103a020

文献信息

• Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C−H Bonds in Aliphatic Amines
  作者：Jaime R. Cabrera-Pardo、Aaron Trowbridge、Manuel Nappi、Kyohei Ozaki、Matthew J. Gaunt

  DOI：10.1002/anie.201706303

  日期：2017.9.18

  The ligand is key: Palladium(II)-catalyzed C−H carbonylation reactions of methylene C−H bonds in secondary aliphatic amines lead to the formation of trans-disubstituted β-lactams in excellent yields and selectivities. The generality of the C−H carbonylation process is aided by the action of xantphos-based ligands.

  配体是关键：钯（II）催化的脂肪族仲胺中亚甲基CH键的CH羰基化反应导致反式二取代的β-内酰胺的形成，具有极高的收率和选择性。基于Xantphos的配体的作用有助于CH羰基化过程的普遍性。
• TAXANE COMPOUND WITH AZETIDINE RING STRUCTURE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1942109A1

  公开（公告）日：2008-07-09

  A compound represented by the general formula (1) [X1 and X2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R1 represents a phenyl group, R2 represents an alkyl group, an alkenyl group, or an alkoxy group, R3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R4 represents hydrogen atom, or an alkyl group, Z1 and Z2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z3 represents cyano group, an alkyl group, an alkenyl group and the like, Z4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and ---- represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一个由通式（1）表示的化合物，其中[X1和X2代表氢原子，卤素原子，羟基等，R1代表苯基，R2代表烷基，烯基或烷氧基，R3代表氢原子，卤素原子，羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子，卤素原子，羟基等，Z3代表氰基，烷基，烯基等，Z4代表烷基，烯基，炔基等，----代表单键或双键]，对包括药物耐药细胞在内的癌细胞表现出高抗肿瘤效果。
• Braschi Ilaria, Cardillo Giuliana, Tomasini Claudia, Venezia Roberto, J. Org. Chem, 59 (1994) N 24, S 7292-7298
  作者：Braschi Ilaria, Cardillo Giuliana, Tomasini Claudia, Venezia Roberto

  DOI：——

  日期：——