(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(1-methyl-1,2-propadienyl)-2-azetidinone | 276244-14-5

• 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: (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(1-methyl-1,2-propadienyl)-2-azetidinone
• 英文别名: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-3-(1-phenyl-1,2-propadienyl)-1-(p-methoxyphenyl)-2-azetidinone
• CAS: 276244-14-5
• 化学式: C₂₄H₂₅NO₅
• 分子量: 407.466
• InChiKey: QOACUTKZRCVAGM-ZFGGDYGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(1-methyl-1,2-propadienyl)-2-azetidinone 在 四丁基碘化铵 、 乙酰氯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以84%的产率得到(3E,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-3-(1-phenylprop-2-ynylidene)azetidin-2-one
  参考文献：
  名称：

  直接基于烯丙醇的立体控制进入取代的（E）-1,3-炔烃†

  摘要：

  通过用AcCl-NaOH（水溶液）处理，从芳基取代的α-烯醇中开发了一种立体选择性合成的1-取代的（E）-2-芳基-丁-1-烯-3-炔烃，包括四取代的烯烃。 。可以通过消除这种解释来解释这种转变。醋酸由δ-氢和最初形成的α-烯丙基乙酸酯中的乙酸酯基团组成。

  DOI：

  10.1039/c2ob26085a
• 作为产物：
  描述：

  (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 草酰氯 、 氯化铵 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(1-methyl-1,2-propadienyl)-2-azetidinone
  参考文献：
  名称：

  Metal-Promoted Allylation, Propargylation, or Allenylation of Azetidine-2,3-diones in Aqueous and Anhydrous Media. Application to the Asymmetric Synthesis of Densely Functionalized 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation during allenylation/propargylation reactions of the keto-beta -lactams. The stereochemistry of the new C3-substituted C3-hydroxy quaternary center was controlled by placing a chiral auxiliary at C4. In this way, the coupling of azetidine-2,3-diones with a variety of propenyl-, propynyl-, and allenylmetal reagents offers a convenient asymmetric entry to potentially bioactive 3-substituted 3-hydroxy-beta -lactams.

  DOI：

  10.1021/jo015704l

文献信息

• Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes
  作者：Benito Alcaide、Pedro Almendros、Teresa Martínez del Campo

  DOI：10.1039/c2ob26085a

  日期：——

  A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl–NaOH (aqueous) system. This transformation might be explained through the elimination of acetic acid, made up of a δ-hydrogen and the acetate group in the initially formed α-allenic acetate.

  通过用AcCl-NaOH（水溶液）处理，从芳基取代的α-烯醇中开发了一种立体选择性合成的1-取代的（E）-2-芳基-丁-1-烯-3-炔烃，包括四取代的烯烃。 。可以通过消除这种解释来解释这种转变。醋酸由δ-氢和最初形成的α-烯丙基乙酸酯中的乙酸酯基团组成。
• New Regiocontrolled Synthesis of Functionalized Pyrroles from 2-Azetidinone-Tethered Allenols
  作者：Benito Alcaide、Pedro Almendros、Rocío Carrascosa、María C. Redondo

  DOI：10.1002/chem.200700788

  日期：2008.1.7

  A new one-pot approach to synthesize densely substituted racemic and enantiopure pyrroles from beta-lactams has been developed. The approach relies on the regiocontrolled cyclization of beta-allenamine intermediates derived from the ring opening of 2-azetidinone-tethered allenols. In this approach four points of diversity are introduced, one of which is the position of the allene moiety on the beta-lactam

  已开发出一种新的一锅法，可从β-内酰胺合成密集取代的外消旋和对映纯吡咯。该方法依赖于衍生自2-氮杂环丁酮系链的烯丙醇的开环的β-亚胺胺中间体的区域控制环化。在这种方法中，引入了四个多样性点，其中之一是β-内酰胺环上丙二烯部分的位置。
• Synthesis of Spiroheterocycles by Palladium-Catalyzed Domino Cycloisomerization/Cross-Coupling of α-Allenols and Baylis-Hillman Acetates
  作者：Benito Alcaide、Pedro Almendros、Teresa Martínez del Campo、M. Teresa Quirós

  DOI：10.1002/chem.200900096

  日期：2009.3.23

  First insights into the reaction between a Baylis–Hillman adduct and an allene moiety have been obtained from the novel domino heterocyclization/cross‐coupling reaction of α‐allenols and Baylis–Hillman acetates, which furnishes [(2,5‐dihydrofuran‐3‐yl)methyl]acrylate derivatives in moderate to good yields.

  第一见解成的Baylis-希尔曼加合物和丙二烯基部分之间的反应已经从新颖多米诺heterocyclization /交叉偶联α-allenols和的Baylis-希尔曼乙酸酯的反应，其配料[（2,5-二氢呋喃-3-获得中等）的产率。
• Diversity-Oriented Preparation of Enantiopure Spirocyclic 2-Azetidinones from α-Oxo-β-lactams through Barbier-Type Reactions followed by Metal-Catalyzed Cyclizations
  作者：Benito Alcaide、Pedro Almendros、Teresa Martínez del Campo、Raquel Rodríguez-Acebes

  DOI：10.1002/adsc.200600502

  日期：2007.3.5

  Novel, simple, and convenient strategies to diversely functionalized spirocyclic β-lactams have been developed by using different metal-mediated carbonyl addition/cyclization reaction sequences. Spirocyclization precursors, 2-azetidinone-tethered homoallylic alcohols, bromohomoallylic alcohols, homopropargylic alcohols, (buta-1,3-dien-2-yl)methanols, and α-allenols have been obtained by regioselective

  通过使用不同的金属介导的羰基加成/环化反应序列，已经开发出新颖，简单和方便的策略来实现多种功能化的螺环β-内酰胺。螺环化前体，2-氮杂环丁酮拴系的均烯丙基醇，溴代均烯丙基醇，均丙炔醇，（buta-1,3-dien-2-yl）甲醇和α-烯醇是通过将稳定的有机金属试剂区域选择性地添加到氮杂环丁烷2中而获得的，3-二酮在水性环境中。上述单环不饱和醇衍生物的钌，银和钯催化的反应提供了oxaspiro-β-内酰胺。
• New Aspects of the Indium Chemistryof Carbonyl-β-lactams
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Raquel Rodríguez-Acebes

  DOI：10.1055/s-2003-39388

  日期：——

  Reactions of racemic as well as optically pure carbonyl-β-lactams with stabilized organo-indium reagents were investigated in aqueous media. The regio- and stereochemistry of the processes were generally good, offering a convenient asymmetric entry to densely functionalized hydroxy-β-lactams.

  研究了外消旋和光学纯羰基-δ-内酰胺与稳定的有机铟试剂在水介质中的反应。反应过程的区域和立体化学性质普遍良好，为获得官能化程度较高的羟基δ-内酰胺提供了便捷的不对称途径。