(3S,4S) 3-amino-4-fluoromethyl-azetidinone | 86455-13-2

• 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: (3S,4S) 3-amino-4-fluoromethyl-azetidinone
• 英文别名: (3S,4S) 4-fluoromethyl-3-amino-2-oxo-azetidine hydrochloride；cis 4-Fluoromethyl-3-amino-2-oxo-azetidine hydrochloride；(3S,4S)-3-amino-4-(fluoromethyl)azetidin-2-one;hydrochloride
• CAS: 86455-13-2；91685-74-4；93712-92-6
• 化学式: C₄H₇FN₂O*ClH
• 分子量: 154.572
• InChiKey: LNLOZOIRVOSVTG-MUWMCQJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S) 3-amino-4-fluoromethyl-azetidinone 生成 [5-[(2S,3S)-3-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(2,2-dimethylpropanoyloxymethoxy)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-2-(fluoromethyl)-4-oxoazetidin-1-yl]tetrazol-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S,4S) 4-fluoromethyl-3-phthalimido-2-oxo-1-azetidine 在 盐酸 、 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3S,4S) 3-amino-4-fluoromethyl-azetidinone
  参考文献：
  名称：

  An enantioselective synthesis of a 4-fluoromethyl-azetidinone

  摘要：

  DOI：

  10.1016/s0040-4039(01)90010-3

文献信息

• Novel 3-amino-2-oxo-azetidine-1-sulfonic acids
  申请人：Roussel Uclaf

  公开号：US04900728A1

  公开（公告）日：1990-02-13

  Novel syn isomers of racemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen linear or branched optionally substituted alkyl of 1 to 12 carbon atoms and optionally substituted alkenyl and alkynyl of 2 to 12 carbon atoms, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is selected from the group consisting of halogen, --CN, --OR', --SR.sub.1 ", azido, thiocyanate, isothiocyanate, and ##STR2## is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R" is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and a heterocycle and R' and R" are individiually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and taken together with the nitrogen to which they are attached form a heterocycle and A.sup.1 is selected from the group consisting of hydrogen, and metal cations and their nontoxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms having antibiotic properties.

  合成新的同分异构体和3-氨基-2-氧代氮杂环-1-磺酸的光学异构体的方法，其中R从氢、1至12碳原子的线性或支链可选取代烷基和2至12碳原子的可选取代烯基和炔基组成的群中选择，R.sub.1为--(CH.sub.2).sub.n --X，n为1至4之间的整数，X从卤素、--CN、--OR'、--SR.sub.1"、叠氮基、硫氰酸基、异硫氰酸基和##STR2##中选择，其中##STR2##从氢和1至4碳原子的烷基组成的群中选择，R"从氢、1至4碳原子的烷基和杂环组成的群中选择，R'和R"分别从氢和1至4碳原子的烷基组成的群中选择，并与它们连接的氮一起形成一个杂环，A.sup.1从氢和金属阳离子及其无毒、药学上可接受的酸盐中选择，波浪线表示具有抗生素性质的顺式形式、反式形式或顺反式形式。
• 3-amino-2-oxo-azetidine-1-sulfonic acids
  申请人：Uclaf; Roussel

  公开号：US05057512A1

  公开（公告）日：1991-10-15

  Novel syn isomers of reacemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR1## wherein R is difluoromethyl, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is selected from the group consisting of halogen, --CN, --OR.sub.1 ', --SR.sub.1 ", azido, thiocyanate, isothiocyanate, and ##STR2## R.sub.1 ' is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.1 " is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and a heterocycle and R' and R" are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and taken together with the nitrogen to which they are attached form a heterocycle and A.sup.1 is selected from the group consisting of hydrogen, and metal cations and their nontoxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms having antibiotic properties.

  该专利描述了一种新的合成异构体和光学异构体的3-氨基-2-氧代氮杂环-1-磺酸，其化学式为##STR1##其中，R为二氟甲基，R.sub.1为--(CH.sub.2).sub.n --X，n为1至4的整数，X选自卤素，--CN，--OR.sub.1 '，--SR.sub.1 "，偶氮基，硫氰酸根，异硫氰酸根和##STR2##R.sub.1 '选自氢和1至4个碳原子的烷基，R.sub.1 "选自氢，1至4个碳原子的烷基和杂环，R'和R"分别选自氢和1至4个碳原子的烷基，并与它们所连接的氮一起形成杂环，A.sup.1选自氢和金属阳离子及其无毒、药学上可接受的酸盐，其中波浪线表示具有抗生素特性的顺式形式、反式形式或顺反式形式。
• Synthese de n-(tetrazol-5-yl) azetidin-2-ones
  作者：Michel Klich、Georges Teutsch

  DOI：10.1016/s0040-4020(01)90553-8

  日期：1986.1
• TEUTSCH, G.;BONNET, A., TETRAHEDRON LETT., 1984, 25, N 15, 1561-1562
  作者：TEUTSCH, G.、BONNET, A.

  DOI：——

  日期：——
• HEYMES, A.;BONNET, A.
  作者：HEYMES, A.、BONNET, A.

  DOI：——

  日期：——