(R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene | 1552276-00-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene
• 英文别名: (3R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene
• CAS: 1552276-00-2
• 化学式: C₉H₁₇IO₂
• 分子量: 284.137
• InChiKey: OJVCJNXZQVABLA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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 在 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 丙酮 、 正戊烷 为溶剂， 反应 4.0h， 生成 (R)-3-((Z)-2-((4R,5S)-4-(tert-butyldimethylsilyloxy)-5-((S)-2-hydroxy-2-methylbut-3-en-1-yl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-4-methylpent-4-enal
  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：

  (R)-2-(2,2-dimethoxyethyl)-3-methylbut-3-en-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以82%的产率得到(R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene
  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
• 作为试剂：
  描述：

  1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-pent-4-en-2-ol 在 2,6-二甲基吡啶 、 四氧化锇 、 (R)-3-(iodomethyl)-5,5-dimethoxy-2-methylpent-1-ene 、 四丁基氟化铵 、 三氧化硫吡啶 、 对甲苯磺酸 、 magnesium 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 10.08h， 生成 (5S,3Z)-4-hydroxy-5-((S)-2-hydroxy-2-methylbut-3-en-1-yl)-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