(3Z,6Z)-3,6-bis(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione | 1610027-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3Z,6Z)-3,6-bis(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione
• 英文别名: (3Z,6Z)-3,6-bis[[(1S,2S,4S)-2-phenylmethoxy-7-oxabicyclo[2.2.1]hept-5-en-2-yl]methylidene]piperazine-2,5-dione
• CAS: 1610027-09-2
• 化学式: C₃₂H₃₀N₂O₆
• 分子量: 538.6
• InChiKey: VOCYDYCSNHWJRK-WSIWPCBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3Z,6Z)-3,6-bis(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,4aR,7aS,9S,11aR,14aS)-7a,14a-bis(benzyloxy)-2,9-dihydroxy-1,7a,8,9,11a,14a-hexahydropyrazino[1,2-a:4,5-a']diindole-6,13(2H,4aH)-dione
  参考文献：
  名称：

  An Efficient Synthesis Strategy to the Core Structure of 6–5–6–5–6-Membered Epipolythiodiketopiperazines

  摘要：

  A concise route to the core structure 1 of 6-5-6-5-6-membered epipolythiodiketopiperazines is described. The strategy relies on construction of the pyrrolines by double nucleophilic opening of a bis(oxabicyclo[2.2.1]heptene) 2, obtained after bidirectional condensation of N,N'-diacetyldiketopiperazine (4) with aldehyde 3.

  DOI：

  10.1021/ol500990f
• 作为产物：
  描述：

  (1S,2R,4S)-2-phenylmethoxy-7-oxabicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 (3Z,6Z)-3,6-bis(((1S,2S,4S)-2-(benzyloxy)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methylene)piperazine-2,5-dione
  参考文献：
  名称：

  An Efficient Synthesis Strategy to the Core Structure of 6–5–6–5–6-Membered Epipolythiodiketopiperazines

  摘要：

  A concise route to the core structure 1 of 6-5-6-5-6-membered epipolythiodiketopiperazines is described. The strategy relies on construction of the pyrrolines by double nucleophilic opening of a bis(oxabicyclo[2.2.1]heptene) 2, obtained after bidirectional condensation of N,N'-diacetyldiketopiperazine (4) with aldehyde 3.

  DOI：

  10.1021/ol500990f

文献信息

• An Efficient Synthesis Strategy to the Core Structure of 6–5–6–5–6-Membered Epipolythiodiketopiperazines
  作者：Hannes F. Zipfel、Erick M. Carreira

  DOI：10.1021/ol500990f

  日期：2014.6.6

  A concise route to the core structure 1 of 6-5-6-5-6-membered epipolythiodiketopiperazines is described. The strategy relies on construction of the pyrrolines by double nucleophilic opening of a bis(oxabicyclo[2.2.1]heptene) 2, obtained after bidirectional condensation of N,N'-diacetyldiketopiperazine (4) with aldehyde 3.