(+/-)-cis-2-(hex-1-ynyl)-cyclopentylmethoxyethoxymethyl ether

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-cis-2-(hex-1-ynyl)-cyclopentylmethoxyethoxymethyl ether
• 英文别名: (1R,2R)-1-hex-1-ynyl-2-(2-methoxyethoxymethoxy)cyclopentane
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: APEKPGQHGNZMDO-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-2-(hex-1-ynyl)-cyclopentylmethoxyethoxymethyl ether 在 lithium nitrate 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (1R*,3S*,4R*,5R*)-(+/-)-3-cyanyl-4-(1-oxopentyl)-2-oxabicyclo[3.3.0]octane
  参考文献：
  名称：

  Diastereoselective formation of anellated tetrahydrofurans using a nitrate radical induced oxidative, self-terminating radical cyclization cascade

  摘要：

  Addition of electrogenerated nitrate radicals to C=C triple bonds in the alkynyl ethers cis-7-9 and trans-8-9 yields anellated tetrahydrofurans 12-16 with high diasteroselectivity through a new type of an oxidative, self-terminating radical cyclization cascade. The reaction probably proceeds via an intramolecular, rate-determining hydrogen atom transfer in the vinyl radical of type 17a, and a subsequent diastereoselective 5-exo radical cyclization. Elimination of nitrogen dioxide terminates the reaction sequence. This reaction is a remarkable example for the creation of a C-O bond by intermolecular addition of an O-centered radical to a pi-system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00564-5
• 作为产物：
  描述：

  Benzoic acid (1S,2S)-2-hex-1-ynyl-cyclopentyl ester 在 正丁基锂 、 sodium methylate 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 24.5h， 生成 (+/-)-cis-2-(hex-1-ynyl)-cyclopentylmethoxyethoxymethyl ether
  参考文献：
  名称：

  Diastereoselective formation of anellated tetrahydrofurans using a nitrate radical induced oxidative, self-terminating radical cyclization cascade

  摘要：

  Addition of electrogenerated nitrate radicals to C=C triple bonds in the alkynyl ethers cis-7-9 and trans-8-9 yields anellated tetrahydrofurans 12-16 with high diasteroselectivity through a new type of an oxidative, self-terminating radical cyclization cascade. The reaction probably proceeds via an intramolecular, rate-determining hydrogen atom transfer in the vinyl radical of type 17a, and a subsequent diastereoselective 5-exo radical cyclization. Elimination of nitrogen dioxide terminates the reaction sequence. This reaction is a remarkable example for the creation of a C-O bond by intermolecular addition of an O-centered radical to a pi-system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00564-5

文献信息

• Diastereoselective formation of anellated tetrahydrofurans using a nitrate radical induced oxidative, self-terminating radical cyclization cascade
  作者：Uta Wille、Lars Lietzau

  DOI：10.1016/s0040-4020(99)00564-5

  日期：1999.8

  Addition of electrogenerated nitrate radicals to C=C triple bonds in the alkynyl ethers cis-7-9 and trans-8-9 yields anellated tetrahydrofurans 12-16 with high diasteroselectivity through a new type of an oxidative, self-terminating radical cyclization cascade. The reaction probably proceeds via an intramolecular, rate-determining hydrogen atom transfer in the vinyl radical of type 17a, and a subsequent diastereoselective 5-exo radical cyclization. Elimination of nitrogen dioxide terminates the reaction sequence. This reaction is a remarkable example for the creation of a C-O bond by intermolecular addition of an O-centered radical to a pi-system. (C) 1999 Elsevier Science Ltd. All rights reserved.