1,1-dibenzylethylene oxide | 41979-18-4

• 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: 1,1-dibenzylethylene oxide
• 英文别名: 2,2-dibenzyl-oxirane；2,2-Dibenzyl-oxiran；2,2-Dibenzyloxirane
• CAS: 41979-18-4
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: GKEGVBQPRXBYOE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±11.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dibenzylethylene oxide 在 氢氧化钾 、 乙醇 、 sodium 作用下， 反应 5.0h， 生成 5,5-Dibenzyl-2-oxo-tetrahydro-furan-3-carboxylic acid
  参考文献：
  名称：

  Moussa, G. E. M.; Basyouni, M. N.; Shaban, M. E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 800 - 801

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-苄基-2-丙烯-1-基)苯 在 水 、 氧气 、 2,3-丁二酮 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以82%的产率得到1,1-dibenzylethylene oxide
  参考文献：
  名称：

  用二乙酰基，氧气和水进行光诱导的烯烃二羟基化

  摘要：

  本文报道的是在温和的反应条件下从烯烃光诱导生产邻二醇。目前使用二乙酰（=丁烷-2,3-二酮），氧​​气和水的二羟基化方法可免除有毒试剂并产生难处理的废物。

  DOI：

  10.1002/hlca.202000228

文献信息

• Titanocene-Catalyzed Reductive Domino Epoxide Ring Opening/Defluorinative Cross-Coupling Reaction
  作者：Zhiyang Lin、Yun Lan、Chuan Wang

  DOI：10.1021/acs.orglett.0c00960

  日期：2020.5.1

  method for efficient synthesis of gem-difluorobishomoallylic alcohols starting from trifluoromethyl-substituted alkenes and epoxides via a titanocene-catalyzed reductive domino reaction, which consists of a Ti(III)-mediated radical-type ring opening and the following allylic defluorinative cross-coupling reaction via sequential radical addition and β-F elimination. Notably, complete regioselectivity and

  本文中，我们报告了一种通过三茂钛催化的还原多米诺反应从三氟甲基取代的烯烃和环氧化物开始，有效合成宝石-二氟双烯丙基烯丙醇的方法，该方法由Ti（III）介导的自由基型开环和以下烯丙基组成通过顺序添加自由基和消除β-F进行的脱氟交叉偶联反应。值得注意的是，在该反应中可以实现完全的区域选择性和对功能性的高耐受性。此外，通过在单个步骤中交叉偶联产物的衍生化，已经制备了多种6-氟-3,4-二氢-2H-吡喃。
• Ligand-Free Nickel-Catalyzed Reductive Allylic Defluorinative Cross-Coupling of α-Trifluoromethyl Alkenes with Epoxides
  作者：Chuan Wang、Zhiyang Lin、Yun Lan

  DOI：10.1055/s-0040-1707170

  日期：2021.9

  We report a reductive allylic defluorinative reaction of α-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gem-difluorobishomoallylic alcohols in moderate to high yields. Notably, this reaction is conducted under mild conditions and requires no external ligand

  我们报告了 α-三氟甲基烯烃与末端环氧化物的还原烯丙基脱氟反应，该反应由碘化物介导的区域选择性开环和镍催化的自由基型交叉偶联组成，以中等至高产率提供多种叔墣二氟二单烯丙基醇. 值得注意的是，该反应是在温和条件下进行的，不需要外部配体或质子供体。
• Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes
  作者：Di Zhang、Hao Li、Dong Yi、Shijing Tu、Zhongyu Qi、Siping Wei、Qiang Fu、Haiyan Fu、Xi Du

  DOI：10.1016/j.tetlet.2021.153461

  日期：2021.11

  Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.

  已经实现了环氧化物与卤代炔烃的 Ti 催化开环炔基化，允许以中等至良好的产率有效和区域选择性地进入各种炔丙醇。开发的协议具有极其温和的反应条件、广泛的底物范围、不同的官能团兼容性以及环氧化物重排为醛的化学特异性。
• 10.1039/d4sc03624g
  作者：Zhu, Yulei、Jia, Jie、Song, Xiangyu、Gong, Chunyu、Xia, Ying

  DOI：10.1039/d4sc03624g

  日期：——

  Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved in double-bond metathesis, like olefin metathesis and carbonyl metathesis, single-bond metathesis has received less attention in the past decade. Herein, we describe the first C(sp3)–O/C(sp3)–F bond formal cross metathesis reaction between gem-difluorinated cyclopropanes (gem-DFCPs)

  复分解反应已被确立为有机合成中的强大工具。虽然双键复分解（如烯烃复分解和羰基复分解）取得了巨大进展，但单键复分解在过去十年中受到的关注较少。在此，我们描述了在铑催化下宝石二氟化环丙烷（ gem -DFCP）和环氧化物之间的第一个C（sp 3 ）–O/C（sp 3 ）–F键形式交叉复分解反应。该反应涉及形成高度亲电子的氟代烯丙基铑中间体，该中间体能够作为弱亲核试剂与环氧化物中的氧原子反应，然后进行 C-F 键重建。使用两个应变环基底是正式交叉复分解成功的关键，其中双应变释放是转化的驱动力。此外，氮杂环丁烷也被证明是这种转化的合适底物。该反应为C(sp 3 )–O和C(sp 3 )–N键的复分解提供了一种新的方法，为单键复分解提供了新的机会。
• Comprehensive analysis of pathway or functionally related gene expression in the National Cancer Institute's anticancer screen
  作者：Ruili Huang、Anders Wallqvist、David G. Covell

  DOI：10.1016/j.ygeno.2005.11.011

  日期：2006.3

  We have analyzed the level of gene coregulation, using gene expression patterns measured across the National Cancer Institute's 60 tumor cell panels (NCI60), in the context of predefined pathways or functional categories annotated by KEGG (Kyoto Encyclopedia of Genes and Genomes), BioCarta, and GO (Gene Ontology). Statistical methods were used to evaluate the level of gene expression coherence (coordinated expression) by comparing intra- and interpathway gene-gene correlations. Our results show that gene expression in pathways, or groups of functionally related genes, has a significantly higher level of coherence than that of a randomly selected set of genes. Transcriptional-level gene regulation appears to be on a "need to be" basis, such that pathways comprising genes encoding closely interacting proteins and pathways responsible for vital cellular processes or processes that are related to growth or proliferation, specifically in cancer cells, such as those engaged in genetic information processing, cell cycle, energy metabolism, and nucleotide metabolism, tend to be more modular (lower degree of gene sharing) and to have genes significantly more coherently expressed than most signaling and regular metabolic pathways. Hierarchical clustering of pathways based on their differential gene expression in the NCI60 further revealed interesting interpathway communications or interactions indicative of a higher level of pathway regulation. The knowledge of the nature of gene expression regulation and biological pathways can be applied to understanding the mechanism by which small drug molecules interfere with biological systems. (c) 2005 Elsevier Inc. All rights reserved.