ethyl (3S,2Z,4E)-3-(tert-butyldimethylsilyloxy)-2-(iodomethylene)hex-4-enoate | 1552275-93-0

• 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 (3S,2Z,4E)-3-(tert-butyldimethylsilyloxy)-2-(iodomethylene)hex-4-enoate
• CAS: 1552275-93-0
• 化学式: C₁₅H₂₇IO₃Si
• 分子量: 410.368
• InChiKey: DCEWEHCZDGXHLG-AZTWYYBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S,2Z,4E)-3-(tert-butyldimethylsilyloxy)-2-(iodomethylene)hex-4-enoate 在 叔丁基锂 、 氧气 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 3.17h， 生成 (4R,5S,3Z)-5-Prop-2-enyl-4-(tert-butyldimethylsilyloxy)-3-[(R)-3-(2,2-dimethoxyethyl)-4-methyl-pent-4-en-1-ylidene]dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion

  摘要：

  With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.076
• 作为产物：
  描述：

  巴豆醛 、 叔丁基二甲基氯硅烷 、 丙炔酸乙酯 在 (R)-2-(O-甲基)苯-CBS-恶唑硼烷 、 aluminum tri-bromide 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到ethyl (3S,2Z,4E)-3-(tert-butyldimethylsilyloxy)-2-(iodomethylene)hex-4-enoate
  参考文献：
  名称：

  Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion

  摘要：

  With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.076