4-[2-(5-methyl)furyl]-4-methylpentyl iodide | 208999-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-[2-(5-methyl)furyl]-4-methylpentyl iodide
• 英文别名: 2-(5-Iodo-2-methylpentan-2-yl)-5-methylfuran
• CAS: 208999-45-5
• 化学式: C₁₁H₁₇IO
• 分子量: 292.16
• InChiKey: XQPCFQXCEXWSEP-UHFFFAOYSA-N

物化性质

• 沸点：
  295.9±28.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[2-(5-methyl)furyl]-4-methylpentyl iodide 在 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 48.42h， 生成 (E and Z)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsulfenyl-2-octene
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Towards a Synthesis of Widdrol

  摘要：

  Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.

  DOI：

  10.3987/com-03-s(p)53
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 吡啶 、 二硫化碳 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 三氯化铝 、 N,N'-dicyclohexylcarbodiimidium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 二甲基亚砜 、 丙酮 为溶剂， 反应 77.42h， 生成 4-[2-(5-methyl)furyl]-4-methylpentyl iodide
  参考文献：
  名称：

  Intramolecular [4+3] Cycloadditions. Towards a Synthesis of Widdrol

  摘要：

  Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.

  DOI：

  10.3987/com-03-s(p)53

文献信息

• The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines
  作者：Michael Harmata、Mehmet Kahraman、Darin E. Jones、Neville Pavri、Susan E. Weatherwax

  DOI：10.1016/s0040-4020(98)00591-2

  日期：1998.8

  N-Phenylsulfonimidoyl chloride reacts with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be deprotonated and alkylated, sometimes with very high diastereocontrol. Upon treatment with fluoride, these silylated benzothiazines undergo desilylation with concomitant cleavage of the carbon-sulfur

  在氯化铝的存在下，N-苯基磺酰亚胺基氯与三甲基甲硅烷基乙烯反应，生成两种苯并噻嗪产品，其中一种已被甲硅烷基化。甲硅烷基化的苯并噻嗪可以被去质子化和烷基化，有时具有非常高的非对映异构控制性。在用氟化物处理后，这些甲硅烷基化的苯并噻嗪进行去甲硅烷基化并伴随碳-硫键的裂解，得到2-烯基亚磺酰苯胺，其可以水解为相应的苯胺。
• Intramolecular 4+3 cycloadditions. Allylic sulfones as precursors to vinylthionium ions
  作者：Michael Harmata、Mehmet Kahraman

  DOI：10.1016/s0040-4039(98)00582-6

  日期：1998.5

  Treatment of a THF solution of(E)-3 with n-BuLi followed by quenching with an electrophile generally results in regioselective alkylation alpha to the sulfone with the alkene possessing (E) stereochemistry in the major product. High selectivity for the (E) alkylation product can be achieved in the presence of small amounts of HMPA. When those (E) alkylation products possessing a diene moiety in the side chain are treated with Lewis acids, 4+3 cycloaddition products are formed in good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.