(+/-)-(Z)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsulfenyl-3-phenylsulfonyl-1-octene | 208999-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(Z)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsulfenyl-3-phenylsulfonyl-1-octene
• 英文别名: (+/-)-(E)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsufenyl-3-phenylsulfonyl-1-octene；2-[(E)-6-(benzenesulfonyl)-7-methoxy-2,6-dimethyl-8-phenylsulfanyloct-7-en-2-yl]-5-methylfuran
• CAS: 208999-46-6
• 化学式: C₂₈H₃₄O₄S₂
• 分子量: 498.708
• InChiKey: RHKZXCPODWTQIR-YYADALCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(Z)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsulfenyl-3-phenylsulfonyl-1-octene 在 偶氮二异丁腈 4-二甲氨基吡啶 、 Amberlite 、 sodium 、 四氯化钛 、 lithium 、 乙二胺 、 三丁基氧化锡 、 正丁醇 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.75h， 生成 (+/-)-widdrol
  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：

  senecioyl cyanide 在 吡啶 、 二硫化碳 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 三氯化铝 、 N,N'-dicyclohexylcarbodiimidium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 101.42h， 生成 (+/-)-(Z)-3,7-dimethyl-2-methoxy-7-[2-(5-methyl)furyl]-1-phenylsulfenyl-3-phenylsulfonyl-1-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

文献信息

• 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.
• Intramolecular [4+3] Cycloadditions. Towards a Synthesis of Widdrol
  作者：Michael Harmata、Mehmet Kahraman、Gilbert Adenu、Charles L. Barnes

  DOI：10.3987/com-03-s(p)53

  日期：——

  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.