2,3-bis((benzyloxy)methyl)oxirane | 136458-56-5

• 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: 2,3-bis((benzyloxy)methyl)oxirane
• 英文别名: 2,3-bis(phenylmethoxymethyl)oxirane
• CAS: 136458-56-5
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: BWXXSADMQUTHRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-bis((benzyloxy)methyl)oxirane 在 偶氮二异丁腈 三正丁基氢锡 、 硫脲 作用下， 以 乙醇 、 苯 为溶剂， 生成 顺-1,4-二苄氧基-2-丁烯
  参考文献：
  名称：

  Studies on the Reaction of Thiiranes with Tributyltin Hydride

  摘要：

  DOI：

  10.1021/jo00107a033
• 作为产物：
  描述：

  1,4-bis-(benzyloxy)-2-butene 在 间氯过氧苯甲酸 作用下， 生成 2,3-bis((benzyloxy)methyl)oxirane
  参考文献：
  名称：

  Design, synthesis and X-ray crystallographic study of new nonsecosteroidal vitamin D receptor ligands

  摘要：

  We designed and synthesized nonsecosteroidal vitamin D receptor (VDR) ligands that formed H-bonds with six amino acid residues (Tyr143, Ser233, Arg270, Ser274, His301 and His393) of the VDR ligand-binding domain. The ligand YR335 exhibited potent transcriptional activity, which was comparable to those of 1 alpha,25-dihydroxyvitamin D-3 and YR301. The crystal structure of the complex formed between YR335 and the VDR ligand-binding domain was solved, which revealed that YR335 formed H-bonds with the six amino acid residues mentioned above. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.047

文献信息

• Gold-Catalysed Activation of Epoxides: Application in the Synthesis of Bicyclic Ketals
  作者：Rengarajan Balamurugan、Raveendra Babu Kothapalli、Ganesh Kumar Thota

  DOI：10.1002/ejoc.201001214

  日期：2011.3

  Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with C≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation

  介绍了金催化从环氧化物生成二醇等价物及其与 C≡C 键的分子内反应生成双环缩酮。该反应主要涉及丙酮化物的形成，其随后在金催化条件下分子内在炔烃上环化。这种方法可以扩展到制造光学纯的双环缩酮。进行氘掺入实验以确定反应机理。
• Copper-Catalyzed Oxyalkynylation of C–S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents
  作者：Julien Borrel、Guillaume Pisella、Jerome Waser

  DOI：10.1021/acs.orglett.9b04157

  日期：2020.1.17

  We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most likely through an alkynyl-episulfonium intermediate. The transformation is copper-catalyzed and compatible with a large array of thiiranes and thietanes

  我们报告使用乙炔基苯并恶唑啉酮试剂（EBXs）来容易地获得带有炔基，苯甲酸酯和碘化物基团的功能化构建基团，从而对噻喃类和硫杂环丁烷进行烷氧基化反应。该反应最有可能通过炔基-is鎓中间体以高原子效率进行。该转化是铜催化的，并且与大量的噻喃和噻吨并存兼容。
• Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines
  申请人：Borhan Babak

  公开号：US20090012120A1

  公开（公告）日：2009-01-08

  An ylide-based aza-Payne rearrangement of 2,3-aziridin- 1 -ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

  基于叶立德的2,3-氮杂环丙醇的aza-Payne重排反应导致了一种高效的吡咯烷制备过程。在碱性反应条件下进行的aza-Payne重排有利于环氧胺的形成。叶立德对环氧化物的亲核攻击产生双阴离子，随后通过5-内攻环闭合产生所需的吡咯烷，从而完成了含3-成员和5-成员氮环的环的传递。这个过程完全保持立体化学的保真度，并可应用于立体位阻的氮杂环丙醇。
• Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]
  作者：Susumi Hatakeyama、Madoka Yoshino、Kohei Eto、Keisuke Takahashi、Jun Ishihara、Yoshiyuki Ono、Hitoshi Saito、Noboru Kubodera

  DOI：10.1016/j.jsbmb.2010.03.041

  日期：2010.7

  Eldecalcitol [1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3, developing code: ED-71] is an analog of active vitamin D3, 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3] that possesses a hydroxypropoxy substituent at the 2β-position of 1,25(OH)2D3. Eldecalcitol has potent biological effects on bone and is now in preparation for approval as a promising medicine for the treatment of osteoporosis in Japan. To

  Eldecalcitol〔1α，25-二羟基2β-（3-羟基丙氧基）维生素d 3，显影代码：ED-71]是活性维生素d的模拟3，1α，25-二羟基维生素d 3 [1,25（OH）2 D 3 ]在1,25（OH）2 D 3的2β位具有羟基丙氧基取代基。降钙素醇对骨骼具有强大的生物学作用，目前正准备批准成为日本治疗骨质疏松症的有前途的药物。为了探索去钙糖醇与相关类似物之间的化学结构与生物活性之间的关系，我们已经合成了具有每个靶类似物固有生物学特性的1-表-elcalccalcitol，3-epi-eldecalcitol和1,3-diepi-eldecalcitol，并评估了它们的生物学特性。回应。据报道，20-表- 1,25（OH）2 d 3，1,25非对映体（OH）2 d 3可以支配在侧链的20位的倒置甲基取代基，节目显着提高与母体化合物1,25（OH）2 D的生物活性3。作为我们对去骨钙
• <i>In Situ</i>Generation of the Coates Catalyst: A Practical and Versatile Catalytic System for the Carbonylation of<i>meso</i>-Epoxides
  作者：Prasad Ganji、David J. Doyle、Hasim Ibrahim

  DOI：10.1021/ol201043d

  日期：2011.6.17

  active catalytic system for the carbonylation of meso- and terminal epoxides to β-lactones is described. The active catalyst, analogous to Coates’ catalyst, is generated in situ from commercially available (TPP)CrCl and Co2(CO)8. This practical system circumvents the preparation of air sensitive cobaltate salts, operates at low catalyst loadings, and allows the carbonylation of functionalized, sterically

  描述了一种高活性的催化体系，用于将内消旋和端环氧化物羰基化为β-内酯。活性催化剂类似于Coates的催化剂，是由可商购获得的（TPP）CrCl和Co 2（CO）8原位生成的。此实际系统规避空气敏感的钴盐的制备中，工作在低催化剂负载，并且允许的官能化的羰基化，空间要求和杂环内消旋环氧化物。