(1E,5E,7E)-(3R,9S)-1-Iodo-3,5,9-trimethyl-undeca-1,5,7-triene | 609842-62-8

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: (1E,5E,7E)-(3R,9S)-1-Iodo-3,5,9-trimethyl-undeca-1,5,7-triene
• 英文别名: (1E,3R,5E,7E,9S)-1-iodo-3,5,9-trimethylundeca-1,5,7-triene
• CAS: 609842-62-8
• 化学式: C₁₄H₂₃I
• 分子量: 318.241
• InChiKey: GARVHKQZHLYJPP-HVHFDEFHSA-N

物化性质

• 沸点：
  318.7±21.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1E,5E,7E)-(3R,9S)-1-Iodo-3,5,9-trimethyl-undeca-1,5,7-triene 在 bis-triphenylphosphine-palladium(II) chloride 三正丁基氢锡 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 nafuredin-γ
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1
• 作为产物：
  描述：

  碘仿 、 (2R,4E,6E,8S)-2,4,8-trimethyl-4,6-decadienal 在 chromium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以81%的产率得到(1E,5E,7E)-(3R,9S)-1-Iodo-3,5,9-trimethyl-undeca-1,5,7-triene
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1

文献信息

• The total synthesis and biological evaluation of nafuredin-γ and its analogues
  作者：Tohru Nagamitsu、Daisuke Takano、Miyuki Seki、Shiho Arima、Masaki Ohtawa、Kazuro Shiomi、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.06.066

  日期：2008.8

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.