1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one | 57288-16-1

• 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: 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one
• 英文别名: methyl 2-[2-(1,3-dioxoisoindol-2-yl)sulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate
• CAS: 57288-16-1
• 化学式: C₂₅H₂₃N₃O₆S
• 分子量: 493.54
• InChiKey: WOKQHKJYVONEMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 1-(1-carboxy-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one 在 苯 、 邻苯二甲酸亚胺 、 silica gel 、 toluene-ethyl acetate 作用下， 以 乙醚 为溶剂， 以to obtain 6.24 g (62% yield) of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one的产率得到1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one
  参考文献：
  名称：

  Azetidine derivatives

  摘要：

  公式I中的新型氮杂四元环衍生物的式子如下：##STR1## 其中R.sub.1是酰胺基团，R.sub.2从以下组中选择：##STR2## 其中R.sub.4、R.sub.5和R.sub.6分别从氢、低烷基和低烯基中选择，n为2或3，当公式IIB为苯时，该基团可以携带1至4个取代基，所述取代基从卤素、低烷基、低烯基和苯中选择，R.sub.3是低烷基，可选地取代1或2个苯基，所述苯基可以取代硝基，公式IIB中的虚线表示双键的可选存在。该专利还涉及一种使用公式I中的氮杂四元环衍生物作为中间体制备头孢菌素酸衍生物的方法。

  公开号：

  US04007202A1

文献信息

• Acetidine derivatives
  申请人：Gist-Brocades N.V.

  公开号：US03962277A1

  公开（公告）日：1976-06-08

  A new azetidine derivative of the formula: ##EQU1## wherein R.sub.1 represents a penicillin- or cephalosporin-amido group, R.sub.2 represents one of the groups of the following formulae: ##EQU2## wherein R.sub.4, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom or a lower alkyl or alkenyl group, n represents 2 or 3 and - in case formula IIB represents a phenyl group - this group may carry one to four further substituents selected from the group consisting of halogen atoms and lower alkyl, lower alkenyl and phenyl groups, R.sub.3 represents an amino group of the formula ##EQU3## wherein R.sub.7 represents a hydrogen atom or a lower alkyl group and R.sub.8 represents a lower alkyl group, or R.sub.3 represents a N,N'-disubstituted hydrazino group wherein the substituents are lower alkyl groups, e.g. the N,N'-diisopropylhydrazino group, or R.sub.3 represents the group --OR.sub.9, wherein R.sub.9 represents a hydrogen atom, a lower alkyl group, which group may be substituted by 1 to 3 halogen atoms or by 1 or 2 phenyl groups, werein the phenyl groups may be substituted by a methoxy or a nitro group, or R.sub.9 represents a phenacyl group or a salt-forming cation, And corresponding azetidine derivatives of formula I wherein the double bond in the propenyl side chain has been shifted from the 2- to the 1-position, which are versatile intermediates in the process of preparing cephalosporanic and penicillanic derivative.

  一种新的环丙烷衍生物的化学式如下：##EQU1## 其中R.sub.1代表青霉素或头孢菌素酰胺基团，R.sub.2代表以下化学式中的一种基团：##EQU2## 其中R.sub.4、R.sub.5和R.sub.6相同或不同，每个代表氢原子或较低的烷基或烯基基团，n代表2或3，- 如果化学式IIB代表苯基团 - 该基团可以携带来自卤素原子和较低的烷基、烯基和苯基团的一到四个进一步的取代基，R.sub.3代表以下化学式的氨基团：##EQU3## 其中R.sub.7代表氢原子或较低的烷基基团，R.sub.8代表较低的烷基基团，或者R.sub.3代表N,N'-二取代的肼基团，其中取代基是较低的烷基基团，例如N,N'-二异丙基肼基团，或者R.sub.3代表--OR.sub.9基团，其中R.sub.9代表氢原子、较低的烷基基团，该基团可以被1到3个卤素原子或1或2个苯基团取代，其中苯基团可以被甲氧基或硝基基团取代，或者R.sub.9代表苯乙酰基团或盐形成阳离子，以及化学式I的相应环丙烷衍生物，其中丙烯基侧链中的双键已经从2位移至1位，这些衍生物是制备头孢菌素和青霉素衍生物的过程中的多功能中间体。
• Process for preparing cephalosporin derivatives
  申请人：Gist-Brocades N.V.

  公开号：US04046761A1

  公开（公告）日：1977-09-06

  Novel azetidine derivatives of the formula ##STR1## wherein R.sub.1 is an acylamido group, R.sub.2 is selected from the group consisting of ##STR2## wherein R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, n is 2 or 3 and -- in the case when formula IIB is a phenyl -- this group may carry 1 to 4 substituents selected from the group consisting of halogen, lower alkyl, lower alkenyl and phenyl, and R.sub.3 is lower alkyl optionally substituted with 1 or 2 phenyls which phenyl groups may be substituted with nitro and a process for their preparation and process for the preparation of cephalosporanic acid derivatives using the azetidines of formula I as intermediates. This is a division of Serial No. 547,948, filed Feb. 7, 1975 now Pat. No. 4,007,202.

  公式为##STR1##的新型氮杂丁烷衍生物，其中R.sub.1为酰胺基团，R.sub.2选自以下组合：##STR2##其中R.sub.4，R.sub.5和R.sub.6分别选自氢，低烷基和低烯基组，n为2或3，当公式IIB为苯时，该基团可以携带1至4个取代基，所选取代基来自卤素，低烷基，低烯基和苯基，R.sub.3为低烷基，可选择地取代1或2个苯基，其中苯基可以被硝基取代，以及使用公式I的氮杂丁烷中间体制备头孢菌素酸衍生物的过程。本申请为1975年2月7日提交的申请号547,948的分案，现已授权专利号为4,007,202。
• Process for the preparation of azetidines
  申请人：Gist-Brocades N.V.

  公开号：US04282145A1

  公开（公告）日：1981-08-04

  New azetidine derivatives of the formula: ##STR1## wherein R.sub.1 represents a penicillin- or cephalosporin-amido group, R.sub.2 represents one of the groups of the following formulae: ##STR2## wherein R.sub.4, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom or a lower alkyl or alkenyl group, n represents 2 or 3 and--in case formula IIB represents a phenyl group--this group may carry one to four further substituents selected from the group consisting of halogen atoms and lower alkyl, lower alkenyl and phenyl groups, R.sub.3 represents an amino group of the formula ##STR3## wherein R.sub.7 represents a hydrogen atom or a lower alkyl group and R.sub.8 represents a lower alkyl group, or R.sub.3 represents a N,N'-disubstituted hydrazino group wherein the substituents are lower alkyl groups, e.g. the N,N'-diisopropylhydrazino group, or R.sub.3 represents the group --OR.sub.9, wherein R.sub.9 represents a hydrogen atom, a lower alkyl group, which group may be substituted by 1 to 3 halogen atoms or by 1 or 2 phenyl groups, wherein the phenyl groups may be substituted by a methoxy or a nitro group, or R.sub.9 represents a phenacyl group or a salt-forming cation, and corresponding azetidine derivatives of formula I wherein the double bond in the propenyl side chain has been shifted from the 2- to the 1-position, which are versatile intermediates in the process of preparing cephalo-sporanic and penicillanic derivatives.

  新的azetidine衍生物的化学式为：##STR1## 其中R.sub.1代表青霉素或头孢菌素酰胺基团，R.sub.2代表以下化学式中的一种：##STR2## 其中R.sub.4、R.sub.5和R.sub.6相同或不同，每个代表氢原子或较低的烷基或烯基基团，n代表2或3，如果化学式IIB代表苯基，则该基团可以携带来自卤素原子和较低的烷基、烯基和苯基组的1至4个进一步的取代基，R.sub.3代表以下化学式的氨基团：##STR3## 其中R.sub.7代表氢原子或较低的烷基基团，R.sub.8代表较低的烷基基团，或R.sub.3代表N，N'-二取代的肼基团，其中取代基是较低的烷基，例如N，N'-二异丙基肼基团，或R.sub.3代表--OR.sub.9基团，其中R.sub.9代表氢原子、较低的烷基基团，该基团可以被1至3个卤素原子或1或2个苯基取代，其中苯基可以被甲氧基或硝基取代，或R.sub.9代表苯乙酰基团或盐形成阳离子，以及化学式I中相应的azetidine衍生物，其中丙烯基侧链中的双键已从2位移动到1位，这些化合物是制备头孢菌素和青霉素衍生物的多功能中间体。
• US4282145A
  申请人：——

  公开号：US4282145A

  公开（公告）日：1981-08-04
• Azetidine derivatives
  申请人：Gist-Brocades N.V.

  公开号：US04007202A1

  公开（公告）日：1977-02-08

  Novel azetidine derivatives of the formula ##STR1## wherein R.sub.1 is an acylamido group, R.sub.2 is selected from the group consisting of ##STR2## wherein R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, n is 2 or 3 and -- in the case when formula IIB is a phenyl - this group may carry one to four substituents selected from the group consisting of halogen, lower alkyl, lower alkenyl and phenyl, and R.sub.3 is lower alkyl optionally substituted with 1 or 2 phenyls which phenyl groups may be substituted with nitro and the dotted lines of formula IIB indicate the optional presence of double bonds and a process for their preparation and process for the preparation of cephalosporanic acid derivatives using the azetidines of formula I as intermediates.

  新型环丙胺衍生物的化学式如下：其中R.sub.1是酰胺基团，R.sub.2从以下组中选择：其中R.sub.4、R.sub.5和R.sub.6分别从氢、低烷基和低烯基组中选择，n为2或3；当化合物IIB为苯基时，该基团可携带一个到四个卤素、低烷基、低烯基和苯基中选择的取代基，R.sub.3是低烷基，可选择性地取代1或2个苯基，这些苯基可能被硝基取代，化合物IIB的虚线表示双键的可选存在；提供了它们的制备方法以及使用化合物I作为中间体制备头孢菌素酸衍生物的方法。