(4R,5S,3Z)-5-(prop-2-enyl)-4-(tert-butyldimethylsilyloxy)-3-(iodomethylene)dihydrofuran-2(3H)-one | 1552275-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5S,3Z)-5-(prop-2-enyl)-4-(tert-butyldimethylsilyloxy)-3-(iodomethylene)dihydrofuran-2(3H)-one
• 英文别名: (3Z,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-3-(iodomethylidene)-5-prop-2-enyloxolan-2-one
• CAS: 1552275-95-2
• 化学式: C₁₄H₂₃IO₃Si
• 分子量: 394.325
• InChiKey: BNBRUOGQWPIMBJ-QMZLHQMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-METHOXY-9-BORABICYCLO[3.3.1]NONANE 、 (R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene 、 (4R,5S,3Z)-5-(prop-2-enyl)-4-(tert-butyldimethylsilyloxy)-3-(iodomethylene)dihydrofuran-2(3H)-one 在 叔丁基锂 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 正戊烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以53%的产率得到(4R,5S,3Z)-4-(tert-Butyldimethylsilyloxy)-3-((R)-3-(2,2-dimethoxyethyl)-4-methylpent-4-en-1-ylidene)-5-((S)-2-hydroxy-2-methylbut-3-en-1-yl)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：

  叔丁基二甲基氯硅烷 在 (R)-2-(O-甲基)苯-CBS-恶唑硼烷 、 aluminum tri-bromide 、 氧气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 (4R,5S,3Z)-5-(prop-2-enyl)-4-(tert-butyldimethylsilyloxy)-3-(iodomethylene)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