(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 | 1552276-01-3

• 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-[(R)-3-(2,2-dimethoxyethyl)-4-methyl-pent-4-en-1-ylidene]dihydrofuran-2(3H)-one
• 英文别名: (3Z,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-3-[(3R)-3-(2,2-dimethoxyethyl)-4-methylpent-4-enylidene]-5-prop-2-enyloxolan-2-one
• CAS: 1552276-01-3
• 化学式: C₂₃H₄₀O₅Si
• 分子量: 424.653
• InChiKey: YTOCZBXNGXZNED-BGAVLCFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• Synthetic studies on polymaxenolides: model studies for constructing dihydropyran portion and synthesis of lower portion
  作者：Yutaka Matsuda、Masaya Kato、Tomonori Kawaguchi、Takayuki Koyama、Yoko Saikawa、Masaya Nakata

  DOI：10.1016/j.tet.2013.12.076

  日期：2014.2

  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.