3-(4-chlorophenyl)-5,5-dimethyl-4-methyleneoxazolidin-2-one | 55476-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-5,5-dimethyl-4-methyleneoxazolidin-2-one
• 英文别名: 3-(4-Chlorophenyl)-5,5-dimethyl-4-methylene-1,3-oxazolidin-2-one；3-(4-chlorophenyl)-5,5-dimethyl-4-methylidene-1,3-oxazolidin-2-one
• CAS: 55476-05-6
• 化学式: C₁₂H₁₂ClNO₂
• mdl: MFCD02647169
• 分子量: 237.686
• InChiKey: BYFMZBBWOMBIJC-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C(Solv: methanol (67-56-1))
• 沸点：
  313.8±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-5,5-dimethyl-4-methyleneoxazolidin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到3-(4-chloro-phenyl)-5,5-dimethyl-oxazolidine-2,4-dione
  参考文献：
  名称：

  Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides

  摘要：

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.034
• 作为产物：
  描述：

  3-(4-chloro-phenylcarbamoyloxy)-3-methyl-butan-2-one 以 水 、 溶剂黄146 为溶剂， 生成 3-(4-chlorophenyl)-5,5-dimethyl-4-methyleneoxazolidin-2-one
  参考文献：
  名称：

  Francis,T.; Thorne,M.P., Canadian Journal of Chemistry, 1976, vol. 54, p. 24 - 30

  摘要：

  DOI：

文献信息

• Rare-Earth-Metal-Complex-Catalyzed Hydroalkoxylation and Tandem Hydroalkoxylation/Cyclohydroamination of Isocyanates: Synthesis of Carbamates and Oxazolidinones
  作者：Xiancui Zhu、Yawen Qi、Yuanqing Yang、Dianjun Guo、Zeming Huang、Lijun Zhang、Yun Wei、Shuangliu Zhou、Shaowu Wang

  DOI：10.1021/acs.inorgchem.1c03673

  日期：2022.2.21

  Novel N,N,N-tridentate β-diketiminato rare-earth-metal dialkyl complexes LRE(CH2SiMe3)2 [RE = Y (1a), Gd (1b), Yb (1c), Lu (1d); L = MeC(NDipp)CHC(Me)N(CH2)2NC4H8, where Dipp = 2,6-iPr2C6H3] have been conveniently synthesized by one step from reactions of the rare-earth-metal trialkyl complexes RE(CH2SiMe3)3(THF)2 (THF = tetrahydrofuran) with a pyrrolidine-functionalized β-diketiminate HL, and their

  新型 N,N,N-三齿 β-二酮亚氨基稀土金属二烷基配合物L RE(CH 2 SiMe 3 ) 2 [RE = Y ( 1a ), Gd ( 1b ), Yb ( 1c ), Lu ( 1d )；L = MeC(NDipp)CHC(Me)N(CH 2 ) 2 NC 4 H 8 , 其中 Dipp = 2,6- i Pr 2 C 6 H 3 ] 由稀土反应一步合成-金属三烷基配合物 RE(CH 2 SiMe 3 ) 3 (THF)2 (THF = 四氢呋喃) 与吡咯烷官能化的 β-二酮亚胺 H L以及它们对异氰酸酯的加氢烷氧基化和串联加氢烷氧基化/环加氢胺化的催化行为已被描述。这些稀土金属催化剂在异氰酸酯的加氢烷氧基化中表现出高效率，在温和的反应条件下以相当低的催化剂负载量（0.04 mol%）提供多种N-烷基和N-芳基氨基甲酸酯衍生物。更重要的是，它们可以促进末端和内部炔丙醇与取代的芳基异
• Structural studies of 1,3-oxazolidine-containing spiropyrans
  作者：B. S. Luk’yanov、V. V. Tkachev、M. B. Luk’yanova、A. N. Utenyshev、R. V. Tyurin、M. S. Korobov、S. M. Aldoshin

  DOI：10.1007/s11172-016-1552-3

  日期：2016.8

  New 3’-(4-chlorophenyl)-5’,5’-dimethyl-2’-oxospiro[(2H)-chromene-2,4’-1,3-oxazolidine] was synthesized to study the donor influence of the chlorine atom at the N-phenyl substituent on the structure and photochromic properties of 1,3-oxazolidine-containing spiropyrans. Photochemical properties of synthesized 1,3-oxazolidine derivatives were studied at room temperature in toluene. The X-ray diffraction

  合成新的3'-(4-氯苯基)-5',5'-二甲基-2'-氧代螺[(2H)-色烯-2,4'-1,3-恶唑烷]以研究氯对供体的影响N-苯基取代基上的原子对含 1,3-恶唑烷的螺吡喃的结构和光致变色性能的影响。在室温下在甲苯中研究合成的 1,3-恶唑烷衍生物的光化学性质。将新化合物的 X 射线衍射参数与之前获得的类似螺吡喃的数据进行了比较。
• Divergent Pd-catalyzed Functionalization of 4-Oxazolin-2-ones and 4-Methylene-2-oxazolidinones and Synthesis of Heterocyclic-Fused Indoles
  作者：Daniel Yescas-Galicia、Rodrigo A. Restrepo-Osorio、Ailyn N. García-González、Roberto I. Hernández-Benítez、José C. Espinoza-Hicks、Carlos H. Escalante、Edson Barrera、Blanca M. Santoyo、Francisco Delgado、Joaquín Tamariz

  DOI：10.1021/acs.joc.2c01563

  日期：2022.10.7

  Palladium-catalyzed functionalization was presently performed on two building blocks: 4-oxazolin-2-ones and 4-methylene-2-oxazolidinones. Direct Heck arylation of 4-oxazolin-2-ones led to a series of 5-aryl-4-oxazolin-2-ones, including analogues with N-chiral auxiliary, in an almost quantitative yield. The Pd(II)-catalyzed homocoupling reaction of 4-oxazolin-2-ones provided novel heterocyclic across-ring

  钯催化的功能化目前在两个结构单元上进行：4-恶唑啉-2-酮和 4-亚甲基-2-恶唑烷酮。4-oxazolin-2-ones 的直接 Heck 芳基化以几乎定量的产率产生一系列 5-aryl-4-oxazolin-2-ones，包括具有 N-手性助剂的类似物。Pd(II) 催化的 4-oxazolin-2-ones 的同源偶联反应提供了新的杂环跨环二烯。同时， N-芳基-4-亚甲基-2-恶唑烷酮的分子内交叉偶联提供了一系列恶唑并[3,4- a]吲哚-3-ones。4-亚甲基-2-恶唑烷酮的进一步官能化提供了取代的吲哚和杂环稠合的吲哚与芳基、溴、甲醇、甲酰基和乙烯基。进行了计算研究以解释甲酰化衍生物的行为。目前开发的方法应用于玫瑰树碱的一种新的正式全合成。
• Lanthanide Mimicking by Magnesium for Oxazolidinone Synthesis
  作者：Rohit Kumar、Biplab Mahata、S. Gayathridevi、K. Vipin Raj、Kumar Vanka、Sakya S. Sen

  DOI：10.1002/chem.202303478

  日期：2024.1.16

  A monomeric magnesium compound was employed as a catalyst for the cascade cyclization of propargylic alcohol and isocyanate, resulting in the formation of pharmaceutically significant oxazolidinone derivatives. This transformation, previously attributed solely to transition metals or lanthanides, signifies a noteworthy advancement.

  采用单体镁化合物作为炔丙醇和异氰酸酯级联环化的催化剂，导致形成具有药学意义的恶唑烷酮衍生物。这种转变以前仅仅归因于过渡金属或镧系元素，标志着一个值得注意的进步。
• Reactions of Acetylenes. I. t-Ethynyl Alcohol with Isocyanates
  作者：Nelson R. Easton、Donald R. Cassady、Robert D. Dillard

  DOI：10.1021/jo01055a510

  日期：1962.8