(E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one | 288585-40-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one
• CAS: 288585-40-0
• 化学式: C₂₀H₂₇IO₂S
• 分子量: 458.404
• InChiKey: KSLAXFOKWNWUJM-DIMJTDRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one 在 Wilkinson's catalyst 、 四(三苯基膦)钯 copper(l) iodide 、 氢气 作用下， 以 甲醇 、 三乙胺 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 38.0h， 生成 3-(phenylthio)uvaricin
  参考文献：
  名称：

  Total Synthesis of Uvaricin

  摘要：

  The first total synthesis of naturally occurring (+)-uvaricin was achieved using three consecutive Sharpless asymmetric dihydroxylation (AD) reactions to place the necessary oxygen functions on a "naked" carbon skeleton in a regio- and enantioselectively controlled manner. The appropriate bis-THF ring system was constructed using a Williamson type etherification reaction on a functionalized bis-mesylate intermediate.

  DOI：

  10.1021/jo980453a
• 作为产物：
  描述：

  9-(tert-butyldimethylsilyloxy)non-1-yne 在 吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 碘 、 三正丁基氢锡 、 sodium hexamethyldisilazane 、 sodium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 丙酮 为溶剂， 生成 (E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  （15 S，16 R，19 S，20 R，34 S）-二磷酸尿嘧啶的全合成

  摘要：

  从对映体纯的（-）-Muricatacin（6）开始的十一步反应序列提供了关键中间体12，然后将其转换为（15 S，16 R，19 S，20 R，34 S）-二古尿嘧啶（1）通过引入乙炔单元和碘内酯合成子15的偶联反应。

  DOI：

  10.1016/0040-4039(96)01086-6

文献信息

• Total synthesis of (15S, 16R, 19S, 20R, 34S)-diepomuricanin
  作者：Hiroyuki Konno、Hidefumi Makabe、Akira Tanaka、Takayuki Oritani

  DOI：10.1016/0040-4039(96)01086-6

  日期：1996.7

  An eleven-step reaction sequence starting from enantiomerically pure (−)-muricatacin (6) afforded the key intermediate 12, which was then converted to (15S, 16R, 19S, 20R, 34S)-diepomuricanin (1) via introduction of an acetylene unit and a coupling reaction with iodo lactone synthon 15.

  从对映体纯的（-）-Muricatacin（6）开始的十一步反应序列提供了关键中间体12，然后将其转换为（15 S，16 R，19 S，20 R，34 S）-二古尿嘧啶（1）通过引入乙炔单元和碘内酯合成子15的偶联反应。
• A Concise Synthesis of Solamin and cis-Solamin, Mono-THF Acetogenins from Annona muricata
  作者：Hidefumi Makabe、Asuka Kuwabara、Yasunao Hattori、Hiroyuki Konno

  DOI：10.3987/com-09-11741

  日期：——

  A concise total synthesis of solamin (1) and cis-solamin (2) was performed using an epoxy alcohol (11) as a versatile chiral building block for synthesizing the stereoisomers of the mono-THF annonaceous acetogenins.
• Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I
  作者：Tomoko Motoyama、Hiromi Yabunaka、Hideto Miyoshi

  DOI：10.1016/s0960-894x(02)00374-8

  日期：2002.8

  To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is one of the common structural features of natural acetogenins, is not an essential structural factor required for the potent inhibition. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and mitochondrial complex I inhibition of dihydroxy-cohibin A, non-THF annonaceous acetogenin analogue
  作者：Hiroyuki Konno、Naoki Hiura、Hidefumi Makabe、Masato Abe、Hideto Miyoshi

  DOI：10.1016/j.bmcl.2003.11.057

  日期：2004.2

  To elucidate the inhibitory action of acetogenins, we synthesized an acetogenin derivative which possesses tetraol in place of the tetrahydrofuran ring and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicate that these hydroxy groups are an essential structural factor though it is not effective as bis-THF hydroxy groups combination. (C) 2003 Elsevier Ltd. All rights reserved.
• Total Synthesis of Uvaricin
  作者：Ahmad Yazbak、Subhash C. Sinha、Ehud Keinan

  DOI：10.1021/jo980453a

  日期：1998.8.1

  The first total synthesis of naturally occurring (+)-uvaricin was achieved using three consecutive Sharpless asymmetric dihydroxylation (AD) reactions to place the necessary oxygen functions on a "naked" carbon skeleton in a regio- and enantioselectively controlled manner. The appropriate bis-THF ring system was constructed using a Williamson type etherification reaction on a functionalized bis-mesylate intermediate.