反式-N-(1E)-1,3-丁二烯-1-基-氨基甲酸2,2,2-三氯乙基酯 | 77627-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 反式-N-(1E)-1,3-丁二烯-1-基-氨基甲酸2,2,2-三氯乙基酯
• 中文别名: 反式-N-（1E）-1,3-丁二烯-1-基氨基甲酸2,2,2-三氯乙基酯
• 英文名称: 2,2,2-trichloroethyl ((E)-buta-1,3-dien-1-yl)carbamate
• 英文别名: 2,2,2-trichloroethyl trans-1,3-butadien-1-yl carbamate；2,2,2-Trichloroethyl (1E)-buta-1,3-dien-1-ylcarbamate；2,2,2-trichloroethyl N-[(1E)-buta-1,3-dienyl]carbamate
• CAS: 77627-82-8
• 化学式: C₇H₈Cl₃NO₂
• 分子量: 244.505
• InChiKey: NERUESRQTJURBD-ONEGZZNKSA-N

物化性质

• 熔点：
  161-163°C
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、乙酸乙酯（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-N-(1E)-1,3-丁二烯-1-基-氨基甲酸2,2,2-三氯乙基酯 、 3-(1,3-benzodioxol-5-yl)-3-buten-2-one 在 对叔丁基邻苯二酚 作用下， 反应 12.0h， 以81%的产率得到2,2,2-trichloroethyl trans-6-acetyl-cis-6-(1,3-benzodioxol-5-yl)-2-cyclohexen-1-yl carbamate
  参考文献：
  名称：

  Diels-Alder reactions of 1-(acylamino)-1,3-dienes

  摘要：

  DOI：

  10.1021/ja00400a054
• 作为产物：
  描述：

  2,2,2-三氯乙醇 、 2,4-戊二烯酸 生成 反式-N-(1E)-1,3-丁二烯-1-基-氨基甲酸2,2,2-三氯乙基酯
  参考文献：
  名称：

  Synthetic applications of N-(acylamino)-1,3-dienes. Control of endo stereoselectivity by the acyl substituent. Stereospecific synthesis of the analgesic Tilidine

  摘要：

  DOI：

  10.1021/jo01337a036

文献信息

• BIS-PHOSPHATE COMPOUND AND ASYMMETRIC REACTION USING THE SAME
  申请人：Terada Masahiro

  公开号：US20120330038A1

  公开（公告）日：2012-12-27

  A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

  提供了一种新型的双磷酸盐化合物，可应用于广泛的反应底物和反应作为不对称反应催化剂，并且可以实现产率高和对映体过量高的不对称反应。该双磷酸盐化合物具有由通用式（1）表示的四芳基骨架。在不对称反应中，存在光学活性的双磷酸盐化合物的情况下，通过使酰胺二烯和不饱和醛化合物相互反应，得到光学活性的酰胺醛。该发明使得像不对称Diels-Alder反应这样的反应能够高效进行，而传统的单磷酸盐化合物很难实现。因此，该发明实现了一种工业上可行的方法，用于生产用作药品、农药和化工产品以及用于这些产品的合成中间体的光学活性酰胺醛、光学活性β-氨基酸衍生物、光学活性二胺化合物、光学活性吡咯烷衍生物和光学活性二氢吡喃衍生物。
• Molecular Design of a Chiral Brønsted Acid with Two Different Acidic Sites: Regio-, Diastereo-, and Enantioselective Hetero-Diels–Alder Reaction of Azopyridinecarboxylate with Amidodienes Catalyzed by Chiral Carboxylic Acid–Monophosphoric Acid
  作者：Norie Momiyama、Hideaki Tabuse、Hirofumi Noda、Masahiro Yamanaka、Takeshi Fujinami、Katsunori Yamanishi、Atsuto Izumiseki、Kosuke Funayama、Fuyuki Egawa、Shino Okada、Hiroaki Adachi、Masahiro Terada

  DOI：10.1021/jacs.6b07150

  日期：2016.9.7

  A chiral Brønsted acid containing two different acidic sites, chiral carboxylic acid-monophosphoric acid 1a, was designed to be a new and effective concept in catalytic asymmetric hetero-Diels-Alder reactions of azopyridinecarboxylate with amidodienes. The multipoint hydrogen-bonding interactions among the carboxylic acid, monophosphoric acid, azopyridinecarboxylate, and amidodiene achieved high catalytic

  含有两个不同酸性位点的手性布朗斯台德酸，手性羧酸 - 单磷酸 1a，被设计为在偶氮吡啶羧酸盐与脒二烯的催化不对称杂狄尔斯 - 阿德耳反应中的一个新的和有效的概念。羧酸、单磷酸、偶氮吡啶羧酸盐和脒二烯之间的多点氢键相互作用实现了高催化和手性效率，一步制备具有优异立体控制的取代的 1,2,3,6-四氢哒嗪。这构成了手性布朗斯台德酸催化的区域选择性、非对映选择性和对映选择性偶氮-杂-Diels-Alder 反应的第一个例子。
• BISPHOSPHATE COMPOUND AND ASYMMETRIC REACTION USING SAME
  申请人：National University Corporation Tohoku University

  公开号：EP2546257A1

  公开（公告）日：2013-01-16

  A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

  本发明提供了一种新型双磷酸盐化合物，它可作为不对称反应催化剂应用于多种反应底物和反应，并能实现不对称反应，产生高产率和高对映体过量。双磷酸酯化合物具有通式（1）表示的四芳基骨架。在不对称反应中，氨基二烯和不饱和醛化合物在光学活性双磷酸盐化合物存在下相互反应，生成光学活性氨基醛。本发明可使诸如不对称 Diels-Alder 反应之类的反应高效进行，而传统的单磷酸盐化合物很难进行这种反应。因此，本发明为生产光学活性氨基醛、光学活性β-氨基酸衍生物、光学活性二胺化合物、光学活性吡咯烷衍生物和光学活性二氢吡喃衍生物提供了一种工业上可行的方法，这些衍生物可用作药物、农药和化学产品等产品以及这些产品的合成中间体。
• OVERMAN L. E.; PETTY C. B.; DOEDENS R. J., J. ORG. CHEM., 1979, 44, NO 23, 4183-4185
  作者：OVERMAN L. E.、 PETTY C. B.、 DOEDENS R. J.

  DOI：——

  日期：——
• OVERMAN, L. E.;FREERKS, R. L.;PETTY, C. B.;CLIZBE, L. A.;ONO, R. K.;TAYLO+, J. AMER. CHEM. SOC., 1981, 103, N 10, 2816-2822
  作者：OVERMAN, L. E.、FREERKS, R. L.、PETTY, C. B.、CLIZBE, L. A.、ONO, R. K.、TAYLO+

  DOI：——

  日期：——