(2R*,3R*)-3-(1,3-dioxoisoindolin-2-yl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carbaldehyde

• 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: (2R*,3R*)-3-(1,3-dioxoisoindolin-2-yl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carbaldehyde
• 英文别名: (3S,4S)-4-Formyl-1-(4-methoxyphenyl)-3-phthalimidoazetidin-2-one；(2S,3S)-3-(1,3-dioxoisoindol-2-yl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carbaldehyde
• 化学式: C₁₉H₁₄N₂O₅
• 分子量: 350.331
• InChiKey: ICJBMSOYZPBHCU-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R*,3R*)-3-(1,3-dioxoisoindolin-2-yl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carbaldehyde 在 sodium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 76.0h， 生成 (3RS,4RS)-4-<(2SR)-3-acetyl-1,3-thiazan-2-yl>-1-(4-methoxyphenyl)-3-phthalimidoazetidin-2-one
  参考文献：
  名称：

  关于某些1-（4-甲氧基苯基）氮杂环丁烷-2-酮对硝酸铈（IV）铵（CAN）的异常行为。结构反应性研究

  摘要：

  在用CAN处理时，乙酰噻唑烷基-氮杂环丁烷-2-酮12进行环转化以提供化合物22，类似于先前研究的氮杂环丁烷-2-酮2a和2b（均在C-4和C-2'处具有相同构型）。相反，类似于先前研究的氮杂环丁烷-2-酮1a和1b（在C-4和C-2'处均具有不同构型），在相同条件下将N-脱甲氧基苯基乙酰噻唑烷基-氮杂环丁烷-2-酮11进行N-脱甲氧基苯基化。乙酰恶唑烷二酮衍生物7的两个差向异构体，在C-4和C-2'处具有相同和不同的构型，均为N-由CAN脱去甲氧基苯基。这些观察结果支持了该机制，该机制先前已提出用于CAN诱导的新型环转化反应。

  DOI：

  10.1016/0040-4020(95)01036-x
• 作为产物：
  描述：

  1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 在 盐酸 、 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 2.0h， 生成 (2R*,3R*)-3-(1,3-dioxoisoindolin-2-yl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carbaldehyde
  参考文献：
  名称：

  Stereoselective preparation of mono- and bis-.beta.-lactams by the 1,4-diaza-1,3-diene - acid chloride condensation: scope and synthetic applications

  摘要：

  The dehydrochlorination of a variety of acid chlorides with triethylamine in the presence of 1,4-diaza 1,3-dienes gives in fair to excellent yields, with total stereoselectivity, cis-4-imino beta-lactams 2, cis-4-formyl beta-lactams 3, or C4,C4'-bis-beta-lactams 4, depending on the reaction conditions. The reaction tolerates a wide variety of substituents, including alkoxy, thiophenoxy, amino, aryl, alkyl, alkylidene, and halogen groups, at the ketene moiety. The synthetic versatility of compounds 3 has been demonstrated by their conversion to intermediates in the synthesis of carbapenems PS-5 and PS-6. Base-induced isomerization of compounds 4 to novel bis-gamma-lactams 5, which in turn are aza analogs of glycaric acids, occurred with total retention of the configuration. This process is formally the elongation of glyoxal in four carbons bearing four contiguous stereocenters with total stereoselectivity in only three or four synthetic steps.

  DOI：

  10.1021/jo00048a027

文献信息

• Acyclic Remote 1,5- and 1,4,5-Stereocontrol in the Catalytic Stereoselective Reactions of β-Lactams with Aldehydes: The Effect of the<i>N</i>-Methylimidazole Ligand
  作者：Paulina Plata、Urszula Klimczak、Bartosz K. Zambroń

  DOI：10.1021/acs.joc.8b02333

  日期：2018.12.7

  N-methylimidazole (N-MI) ligand in the Pd(0)/InI-promoted allylations of aldehydes with β-lactam-derived organoindiums enables the reaction of azetidin-2-ones with diversely substituted allyl moieties, inert under previously reported conditions. As a result, allylations and crotylations of a variety of aromatic and aliphatic aldehydes with previously unavailable chiral ε-amido-allylindiums bearing α-, β-

  所述的应用Ñ甲基咪唑（Ñ -MI）配体在钯（0）/ INI-推进与β内酰胺衍生的organoindiums醛的烯丙基化使的反应氮杂环丁烷-2-酮与不同地取代的烯丙基部分，惰性下先前报告的状况。结果，开发了多种芳香族和脂肪族醛与先前不可用的带有α-，β-或γ-取代的烯丙基片段的手性ε-酰胺基烯丙基的烯丙基化和丁烯酰化。反应在热力学控制下进行，高效的远程1,5-或1,4,5-立体控制可提供（3 Z）-2,5-抗-2,6- syn-或（3 Z）的多样性-2,5-辛-2,6-抗-取代的烯二醇，氨基醇和均烯丙基醇，产率中等至高，且具有非对映选择性。详细研究了β-内酰胺和醛的结构和手性对产物收率和立体化学的影响。
• Useful Dual Diels–Alder Behavior of 2-Azetidinone-Tethered Aryl Imines as Azadienophiles or Azadienes: A -Lactam-Based Stereocontrolled Access to Optically Pure Highly Functionalized Indolizidine Systems
  作者：Benito Alcaide、Pedro Almendros、Jose M. Alonso、Moustafa F. Aly

  DOI：10.1002/chem.200304712

  日期：2003.7.21

  diene in the presence of different Lewis acids. The effect of the amount of catalyst on the conversion rate as well as on the product ratio has been studied. Under standard reaction conditions, indium(III) chloride and zinc(II) iodide provided the best yields, and indium(III) triflate the highest diastereoselectivity in the Lewis acid promoted aza-Diels-Alder cycloaddition. Treatment of the aforementioned

  已经发现衍生自4-氧杂氮杂环丁烷-2-甲醛的亚胺是通用的Diels-Alder试剂，因为它们表现出两种反应模式。在不同的路易斯酸存在下，2-氮杂环丁酮系链的亚胺与Danishefsky的二烯进行非对映选择性反应。已经研究了催化剂的量对转化率以及产物比率的影响。在标准反应条件下，氯化铟（III）和碘化锌（II）提供的收率最高，而三氟甲磺酸铟（IIIflate）在路易斯酸中促进的氮杂-狄尔斯-阿尔德环加成反应的非对映选择性最高。用环戊二烯，2,3-二甲基-1,3-丁二烯或3处理上述亚胺，4-二氢-2 H-吡喃导致由反电子需求缩合产生的环加合物，其中涉及β-内酰胺系的芳基亚胺作为杂二烯组分。另外，已经开发了从β-内酰胺制备吲哚并立定的第一种方法。该过程涉及伴随有环化作用的氮杂-Diels-Alder环加合物中β-内酰胺环的酰胺键裂解。当与对映体纯的底物进行反应时，发生完全手性转移。
• 3-substituted carbacephems
  申请人：Pfizer Inc.

  公开号：US05716948A1

  公开（公告）日：1998-02-10

  A compound of formula (I) or a salt thereof, wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4 represents hydrogen or up to four substituents, which may be present on any of the carbon atoms in the ring system shown, selected from alkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, amino, alkylamino, acylamino, dialkylamino, CO.sub.2 R, CONR.sub.2, SO.sub.2 NR.sub.2 where R is hydrogen or alkyl, aryl and heterocyclyl, which may be the same or different and wherein any R.sup.4 alkyl substituent is optionally substituted by one or more substituents selected from the list from which R.sup.4 is selected; Y is O, S, SO or SO.sub.2 ; and m is 1 or 2, a process for its preparation, use as an antibiotic and intermediates thereto.

  化合物式(I)或其盐，其中R.sup.1是氢，甲氧基或甲酰胺基; R.sup.2是酰基，特别是一种抗菌活性头孢菌素的酰基; CO.sub.2 R.sup.3是羧基或羧酸盐离子，或R.sup.3是容易去除的羧保护基或药学上可接受的盐形成基或体内水解酯基; R.sup.4代表氢或最多四个取代基，在所示环系中的任何碳原子上可能存在，选自烷基，烯基，炔基，烷氧基，羟基，卤素，氨基，烷基氨基，酰胺基，二烷基氨基，CO.sub.2 R，CONR.sub.2，SO.sub.2 NR.sub.2，其中R是氢或烷基，芳基和杂环基，可以相同也可以不同，并且其中任何R.sup.4烷基取代基可以选择性地被来自R.sup.4选择列表的一个或多个取代基取代; Y是O，S，SO或SO.sub.2; m为1或2，其制备过程，用作抗生素的用途和中间体。
• Diastereoselective synthesis of bis-beta-lactams
  作者：Ajay K. Bose、John F. Womelsdorf、Lalitha Krishnan、Zofia Urbanczyk-Lipkowska、Dennis C. Shelly、Maghar S. Manhas

  DOI：10.1016/s0040-4020(01)80972-8

  日期：1991.7

  Schiff bases derived from (+/-)-4-aldehydo-2-azetidinones react with acid chlorides and triethylamine to produce (+/-)-bis-beta-lactams in a diastereoselective fashion. The steric course of beta-lactam formation was determined in one case by using chiral HPLC separation of enantiomers. Definitive evidence in support of this enantiospecific course of beta-lactam formation was obtained from single crystal X-ray diffraction studies on a racemic bis-beta-lactam.
• Tributyltin hydride addition to nitroalkenes: a convenient procedure for the conversion of nitroalkenes into nitroalkanes and carbonyl compounds
  作者：Claudio Palomo、Jesus M. Aizpurua、Fernando P. Cossio、Jesus M. Garcia、M. Concepcion Lopez、Mikel Oiarbide

  DOI：10.1021/jo00294a020

  日期：1990.3