ethyl (E)-(-)-2-bromo-3-<(4'R)-(3'-t-butyloxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)>acrylate | 240137-29-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-(-)-2-bromo-3-<(4'R)-(3'-t-butyloxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)>acrylate
• 英文别名: tert-butyl (4R)-4-[(E)-2-bromo-3-ethoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 240137-29-5
• 化学式: C₁₅H₂₄BrNO₅
• 分子量: 378.263
• InChiKey: TUXJDDNKNZUKES-MXBGMFSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 ethyl (E)-(-)-2-bromo-3-<(4'R)-(3'-t-butyloxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)>acrylate 在 六甲基磷酰三胺 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以56%的产率得到tert-butyl (4R)-4-[(E)-2-ethoxycarbonyl-3,3,3-trifluoroprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  A one-pot synthesis of (E)-α-bromo-α,β-unsaturated esters and their trifluoromethylation: a general and stereoselective route to (E)-α-trifluoromethyl-α,β-unsaturated esters

  摘要：

  Bromination of a phosphonate anion derived in situ from ethyl bis (2,2 2 -trifluoroethyl)phosphonoacetate 3 followed by the addition of aldehydes produced (E)-alpha -bromo-alpha,beta -unsaturated esters 5 stereo selectively. The treatment of 5 with FSO2CF2CO2Me and CuI in DMF/HMPA provided (E)-alpha -trifluoromethyl-alpha,beta -unsaturated esters 6. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01153-4
• 作为产物：
  描述：

  乙基[二(2,2,2-三氟乙氧基)氧膦基]乙酸 、 3-反-溴碳-2,2'-二甲基氧酸酯 以52%的产率得到ethyl (E)-(-)-2-bromo-3-<(4'R)-(3'-t-butyloxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)>acrylate
  参考文献：
  名称：

  A one-pot synthesis of (E)-α-bromo-α,β-unsaturated esters and their trifluoromethylation: a general and stereoselective route to (E)-α-trifluoromethyl-α,β-unsaturated esters

  摘要：

  Bromination of a phosphonate anion derived in situ from ethyl bis (2,2 2 -trifluoroethyl)phosphonoacetate 3 followed by the addition of aldehydes produced (E)-alpha -bromo-alpha,beta -unsaturated esters 5 stereo selectively. The treatment of 5 with FSO2CF2CO2Me and CuI in DMF/HMPA provided (E)-alpha -trifluoromethyl-alpha,beta -unsaturated esters 6. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01153-4

文献信息

• Optically Pure Aminopolyols and Polyoxamic Acid Derivatives from Aziridine-2-carboxylates
  作者：Heribert Dollt、Volker Zabel

  DOI：10.1071/c98026

  日期：——

  Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1′,3′- dioxolan-4′-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an α-bromoacrylate induced a high (3R*,4′S*) selectivity in the Michael addition with an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent effects influencing the cis/trans ratio of aziridine formation are discussed.

  从光学纯的顺式和反式乙基中可以很容易地制备出各种新的手性结构单元。 纯的顺式和反式乙基 3-(1′,3′-二氧戊环-4′-基)氮丙啶-2-羧酸酯。A α-溴丙烯酸酯的烯丙基位置上的立体化学纯的 1,3-二氧戊环。 α-溴丙烯酸酯的烯丙基位置上的立体化学纯 1,3-二氧戊环可诱导出高 (3R*,4′S*) 选择性。在诱导中心的氧 诱导中心的氧与带有大取代基的氮交换后，研究了这一新基团的定向影响。 考察了这一新基团的导向作用。溶剂效应 影响氮丙啶形成的顺式/反式比例的溶剂效应。 形成的顺式/反式比例的溶剂效应进行了讨论。
• A one-pot synthesis of (E)-α-bromo-α,β-unsaturated esters and their trifluoromethylation: a general and stereoselective route to (E)-α-trifluoromethyl-α,β-unsaturated esters
  作者：Feng-Ling Qing、Xingang Zhang

  DOI：10.1016/s0040-4039(01)01153-4

  日期：2001.8

  Bromination of a phosphonate anion derived in situ from ethyl bis (2,2 2 -trifluoroethyl)phosphonoacetate 3 followed by the addition of aldehydes produced (E)-alpha -bromo-alpha,beta -unsaturated esters 5 stereo selectively. The treatment of 5 with FSO2CF2CO2Me and CuI in DMF/HMPA provided (E)-alpha -trifluoromethyl-alpha,beta -unsaturated esters 6. (C) 2001 Elsevier Science Ltd. All rights reserved.