2,3-epoxydodecan-1-ol | 123932-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2,3-epoxydodecan-1-ol
• 英文别名: (3-nonyloxiran-2-yl)methanol
• CAS: 123932-69-4
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: WFHRKQDHNGOVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-epoxydodecan-1-ol 在 diethylzinc 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672
• 作为产物：
  描述：

  反式-2-十二烯-1-醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到2,3-epoxydodecan-1-ol
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.

  DOI：

  10.1021/jo9905672

文献信息

• Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO₂ : A Shortcut to (<i>S</i> )-(+)-Lavandulol
  作者：Yuki Takada、Joaquim Caner、Selvam Kaliyamoorthy、Hiroshi Naka、Susumu Saito

  DOI：10.1002/chem.201704099

  日期：2017.12.19

  We report herein a regio‐ and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)‐loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated

  我们在此报告了一种利用钯（II）负载的二氧化钛对烯丙基醇进行区域和立体选择性光催化氢解反应以形成不饱和烃的方法。该反应在室温下在光照射下进行，而不会产生化学计量的盐废物。烯烃和饱和醇部分耐受反应条件。将氢原子选择性地掺入到烯丙基官能团的较少空间拥挤的碳中。该规程允许通过避免其他必要的保护/脱保护步骤从（R）-（-）-香芹酮短程合成（S）-（+）-lavandulol 。
• Visible-Light-Promoted Reduction of Epoxides, Hydroxysulfonates, and Halohydrines with Alkyltitanium Alkoxides
  作者：Artyom Mikhaliov、Aliaksei Flerko、Dziyana Atroshchanka、Aliaksei Harakhouski、Arsenii Budko、Kirill Stasko、Andrei Bialkevich、Siarhei Shepialevich、Yahor Rusakovich、Alaksiej Hurski

  DOI：10.1021/acs.orglett.3c03802

  日期：2024.1.12

  Alkyltitanium alkoxides generally serve as nucleophiles in reactions with carbonyl compounds and cross-coupling. Their application as reductants is known but remains underdeveloped. Here, we report that irradiation with visible light makes these organometallic compounds efficient reducing agents for the dehalogenation of 1,2- and 1,3-haloalcohols. This reaction was utilized for the reduction of epoxides

  烷基钛醇盐通常在与羰基化合物的反应和交叉偶联中充当亲核试剂。它们作为还原剂的应用是已知的，但仍未得到开发。在这里，我们报告可见光照射使这些有机金属化合物成为 1,2- 和 1,3- 卤代醇脱卤的有效还原剂。该反应用于环氧化物和磺酸盐的还原，该反应通过一系列原位卤代醇形成和光化学脱卤进行。酯、酰胺、腈、炔和远程溴基团在反应条件下是稳定的。
• THERMOPLASTIC RESIN FILM WITH SATISFACTORY PRINTABILITY
  申请人：Yupo Corporation

  公开号：EP1172400A1

  公开（公告）日：2002-01-16

  Described is a thermoplastic resin film having on a surface thereof a hydroxy-modified imine polymer containing repeating units represented by the following general formula (I) in an amount of 5 mol% or more based on the total of repeating units. This thermoplastic resin film has ink transfer, adhesion and aging stability, and excellent printability of generating no back ghost when offset printing using oxidation polymerization type ink is performed on both faces.

  所述的是一种热塑性树脂薄膜，其表面含有羟基改性亚胺聚合物，该聚合物含有以下通式 (I) 所代表的重复单元，其含量为重复单元总量的 5 mol% 或以上。这种热塑性树脂薄膜具有油墨转移性、附着性和老化稳定性，而且在使用氧化聚合型油墨进行胶版印刷时，两面都不会产生重影，具有极佳的印刷适性。
• Thermoplastic resin film satisfactory in printability
  申请人：YUPO CORPORATION

  公开号：US20020054991A1

  公开（公告）日：2002-05-09

  Described is a thermoplastic resin film having on a surface thereof a hydroxy-modified imine polymer containing repeating units represented by the following general formula (I) in an amount of 5 mol % or more based on the total of repeating units. This thermoplastic resin film has ink transfer, adhesion and aging stability, and excellent printability of generating no back ghost when offset printing using oxidation polymerization type ink is performed on both faces 1 .

  所述热塑性树脂薄膜的表面含有羟基改性亚胺聚合物，该聚合物含有以下通式 (I) 所代表的重复单元，其含量为重复单元总量的 5 mol % 或以上。这种热塑性树脂薄膜具有油墨转移性、附着性和老化稳定性，并且在使用氧化聚合型油墨进行胶版印刷时，两面都不会产生重影，具有优异的印刷适性。 1 .
• US6586106B2
  申请人：——

  公开号：US6586106B2

  公开（公告）日：2003-07-01