2-(trichloromethyl)-4,5-dihydro-4-vinyloxazole | 271260-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(trichloromethyl)-4,5-dihydro-4-vinyloxazole
• 英文别名: 2-trichloromethyl-4-vinyloxazoline；Oxazole, 4-ethenyl-4,5-dihydro-2-(trichloromethyl)-；4-ethenyl-2-(trichloromethyl)-4,5-dihydro-1,3-oxazole
• CAS: 271260-81-2
• 化学式: C₆H₆Cl₃NO
• 分子量: 214.479
• InChiKey: CRULYGAMSFOICG-UHFFFAOYSA-N

物化性质

• 沸点：
  181.5±40.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(trichloromethyl)-4,5-dihydro-4-vinyloxazole 在 吡啶 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 2.5h， 以91%的产率得到N-[1-(hydroxymethyl)prop-2-en-1-yl]trichloroacetamide
  参考文献：
  名称：

  2-三氯甲基-4-乙烯基恶唑啉的新型合成及其通过环裂解反应衍生化*

  摘要：

  提出了一种新颖有效的环保方法，用于合成2-三氯甲基-4-乙烯基恶唑啉，该方法涉及路易斯酸催化的衍生自丁-3-烯-1,2-二醇的双亚氨酸酯的环化反应。通过与水，氢溴酸，盐酸和乙酸发生开环反应生成烯丙胺衍生物，证明了2-三氯甲基-4-乙烯基恶唑啉的衍生化潜力。

  DOI：

  10.1007/s10593-012-1077-0
• 作为产物：
  描述：

  but-1-ene-3,4-diylbis(trichloroacetimidate) 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以96%的产率得到2-(trichloromethyl)-4,5-dihydro-4-vinyloxazole
  参考文献：
  名称：

  2-三氯甲基-4-乙烯基恶唑啉的新型合成及其通过环裂解反应衍生化*

  摘要：

  提出了一种新颖有效的环保方法，用于合成2-三氯甲基-4-乙烯基恶唑啉，该方法涉及路易斯酸催化的衍生自丁-3-烯-1,2-二醇的双亚氨酸酯的环化反应。通过与水，氢溴酸，盐酸和乙酸发生开环反应生成烯丙胺衍生物，证明了2-三氯甲基-4-乙烯基恶唑啉的衍生化潜力。

  DOI：

  10.1007/s10593-012-1077-0

文献信息

• Catalytic Asymmetric Synthesis of Chiral Allylic Esters
  作者：Jeffrey S. Cannon、Stefan F. Kirsch、Larry E. Overman

  DOI：10.1021/ja106685w

  日期：2010.11.3

  A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective S(N)2' substitution with a variety of carboxylic acids

  已经开发了一种广泛有用的催化对映选择性合成从前手性 (Z)-2-烯烃-1-醇的支链烯丙酯。起始烯丙醇通过与三氯乙腈反应，在原位或在单独的步骤中转化为其三氯乙酰亚胺中间体，并且该中间体在钯的存在下用各种羧酸进行干净的对映选择性 S(N)2' 取代（ II)催化剂(R(p),S)-di-μ-乙酰基双[(η(5)-2-(2'-(4'-甲基乙基)恶唑啉基)环戊二烯基-1-C,3'-N)( η(4)-四苯基环丁二烯)钴]二钯，(R(p),S)-[COP-OAc](2)，或其对映异构体。定义了这种有用的催化不对称烯丙基酯化的范围和限制。
• Synthesis of Unnatural Amino Acids via Suzuki Cross-Coupling of Enantiopure Vinyloxazolidine Derivatives
  作者：Mark Sabat、Carl R. Johnson

  DOI：10.1021/ol005645i

  日期：2000.4.1

  S)-alpha-Amino alcohols and alpha-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal

  通过钯催化的交叉偶联Suzuki反应合成了（R和S）-α-氨基醇和α-氨基酸，包括4-甲氧基高苯丙氨酸，并带有各种非天然的侧链。由常见的非手性前体2-丁烯-1,4-二醇合成的关键结构单元1和2，利用假单胞菌洋葱脂肪酶催化的动力学拆分，制成对映体纯净的。描述了铃木交叉偶联和随后氧化所得α-氨基醇的最佳条件。
• The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes
  作者：Jian-Jun Feng、Tao-Yan Lin、Chao-Ze Zhu、Huamin Wang、Hai-Hong Wu、Junliang Zhang

  DOI：10.1021/jacs.6b00386

  日期：2016.2.24

  Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst

  已经开发了乙烯基氮丙啶与炔烃的催化剂控制的发散分子间环加成。以[Rh(NBD)2]BF4为催化剂，在温和的反应条件下实现了底物范围广、立体选择性高的[3+2]环加成反应。此外，乙烯基氮丙啶的手性可以完全转移到 [3 + 2] 环加合物上。当催化剂改为 [Rh(η(6)-C10H8) (COD)]SbF6 时，在其他相同的条件下选择性地形成了替代的 [5 + 2] 环加合物。
• Novel Catalysts for the Overman Rearrangement
  作者：Aigars Jirgensons、Ieva Jaunzeme

  DOI：10.1055/s-2005-918952

  日期：——

  PtCl 2 , PtCl 4 , AuCl, and AuCI, were found to be efficient catalysts for the Overman rearrangement of O-allyltrichloroacetimidates to N-allyltrichloroacetamides.

  PtCl 2 、PtCl 4 、AuCl 和AuCl 被发现是O-烯丙基三氯乙酰亚胺酯Overman 重排为N-烯丙基三氯乙酰胺的有效催化剂。
• An Oligomer-Based Approach to Skeletal Diversity in Small-Molecule Synthesis
  作者：David A. Spiegel、Frank C. Schroeder、Jeremy R. Duvall、Stuart L. Schreiber

  DOI：10.1021/ja065724a

  日期：2006.11.1

  Access to small molecules of widely varying molecular shapes has been identified as an enabling step in the discovery of biologically active materials. In this communication we introduce an approach to the systematic development of architecturally distinct chemical compounds based upon the assembly of reactive monomers into linear oligomers, each of which encodes a unique molecular framework under a common set of reaction conditions. Certain products of the initial chemical transformation (Ru-catalyzed metathesis reaction) encode additional skeletons upon treatment with a second common set of reagents (Diels-Alder dienophiles). Application of this oligomerization approach has led to the discovery of a previously unreported tandem ene-yne-yne metathesis-6pi-electrocyclization-1,5-hydride migration that converts a linear substrate into a complex tricyclic 1,3-diene in a single step. Thus, the reported strategy might serve not only as a generator of skeletally diverse small molecules but also as a discovery platform for the identification of novel chemical transformations.