2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(5-butylfuran-2-yl)ethane-1,1,2-tricarboxylate | 1177010-00-2

• 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: 2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(5-butylfuran-2-yl)ethane-1,1,2-tricarboxylate
• CAS: 1177010-00-2
• 化学式: C₂₁H₃₂O₇
• 分子量: 396.481
• InChiKey: IEVGTEAUSDYYLL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(5-butylfuran-2-yl)ethane-1,1,2-tricarboxylate 在 lithium aluminium tetrahydride 、 水 、 sodium sulfate 作用下， 以 乙醚 为溶剂， 以34%的产率得到
  参考文献：
  名称：

  Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives

  摘要：

  Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bis-oxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.016
• 作为产物：
  描述：

  2-正丁基呋喃 、 1,1-diethyl 2-tert-butyl ethenetricarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 、 (3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 作用下， 以 四氢呋喃 为溶剂， 生成 2-O-tert-butyl 1-O,1-O-diethyl (2S)-2-(5-butylfuran-2-yl)ethane-1,1,2-tricarboxylate 、 2-O-tert-butyl 1-O,1-O-diethyl (2R)-2-(5-butylfuran-2-yl)ethane-1,1,2-tricarboxylate
  参考文献：
  名称：

  Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives

  摘要：

  Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bis-oxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.016

文献信息

• Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives
  作者：Shoko Yamazaki、Shinichi Kashima、Taiki Kuriyama、Yuko Iwata、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1016/j.tetasy.2009.05.016

  日期：2009.6

  Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bis-oxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee. (C) 2009 Elsevier Ltd. All rights reserved.