(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-iodophenol | 908373-06-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-iodophenol
• 英文别名: 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodophenol；(E)-2-(3,7-dimethylocta-2,6-dienyl)-4-iodophenol；2-geranyl-4-iodophenol
• CAS: 908373-06-8
• 化学式: C₁₆H₂₁IO
• 分子量: 356.247
• InChiKey: VFZVNBNWRASNFM-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-iodophenol 在 palladium diacetate 4-二甲氨基吡啶 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 methyl (E)-3-[4-(acetyloxy)-3-[(2E)-3,7-dimethyl-2,6-octadienyl]phenyl]-2-propenoate
  参考文献：
  名称：

  Artepillin C isoprenomics: Design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity

  摘要：

  We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics. We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield. Reactivity of artepillin C and its isoprene analogues with ABTS (2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonate)) radical cations showed only a slight difference among the molecules. The isoprene side-chain elongation analogues of artepillin C showed almost the same inhibitory activity against RLM lipid peroxidation as artepillin C. Artepillin C and its isoprene analogues had very weak RLM uncoupling activity. Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation. From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity. We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.015
• 作为产物：
  描述：

  香叶醇 在 氯化亚砜 、 三正丁胺 、 sodium hydride 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.17h， 生成 (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-iodophenol
  参考文献：
  名称：

  无催化剂光介导多烯环化

  摘要：

  多烯环化反应是高效且独特的仿生转化，可从其无环前体产生复杂的多环分子。近年来，随着可见光的使用，已经开发了各种阳离子介导和自由基介导的合成方法来获得高度非对映选择性环化。在本文中，我们报道了在酚环不同位置含有溴基和氯基的香叶基酚的可见光介导、无催化剂级联环化。在不使用任何光催化剂的六氟-2-丙醇中，使用蓝色 LED 灯以高立体选择性获得所需的环化产物。卤素（特别是氯或溴）的存在对于这种环化的成功至关重要，使用蓝色 LED 灯代替绿色 LED 灯也是如此。尽管这一成功的确切原因尚不清楚，但讨论了一些可能的解释，并且光反应的进一步控制研究应该成为该领域任何努力的一部分。

  DOI：

  10.1016/j.tet.2024.133910

文献信息

• Organic Photocatalytic Cyclization of Polyenes: A Visible-Light-Mediated Radical Cascade Approach
  作者：Zhongbo Yang、Han Li、Long Zhang、Ming-Tian Zhang、Jin-Pei Cheng、Sanzhong Luo

  DOI：10.1002/chem.201503118

  日期：2015.10.12

  A visible‐light‐mediated, organic photocatalytic stereoselective radical cascade cyclization of polyprenoids is described. The desired cascade cyclization products are achieved in good yields and high stereoselectivities with eosin Y as photocatalyst in hexafluoro‐2‐propanol. The catalyst system is also suitable for 1,3‐dicarbonyl compounds, which require only catalytic amounts of LiBr to promote the

  描述了聚戊二烯的可见光介导的有机光催化立体选择性自由基级联环化反应。以曙红Y作为六氟-2-丙醇中的光催化剂，可以以高收率和高立体选择性获得所需的级联环化产物。该催化剂体系也适用于1,3-二羰基化合物，这些化合物仅需要催化量的LiBr即可促进相应烯醇的形成。
• Chiral Lewis Base-Assisted Brønsted Acid (LBBA)-Catalyzed Enantioselective Cyclization of 2-Geranylphenols
  作者：Akira Sakakura、Masayuki Sakuma、Kazuaki Ishihara

  DOI：10.1021/ol201032t

  日期：2011.6.17

  Brønsted acids (Chiral LBBAs) have been designed as new organocatalysts for biomimetic enantioselective cyclization. A salt of a chiral phosphonous acid diester with FSO3H catalyzes the enantioselective cyclization of 2-geranylphenols to give the desired trans-fused cyclized products with high diastereo- and enantioselectivities (up to 98:2 dr and 93% ee).

  手性Lewis碱辅助的布朗斯台德酸（手性LBBA）已被设计为仿生对映选择性环化的新型有机催化剂。与FSO手性亚膦酸二酯的盐3 ħ催化2- geranylphenols对映选择性环化，得到所需的反式稠合环化产品具有高diastereo-和对映选择性（高达98：2博士和93％ee）的。
• Selective Bromocyclization of 2-Geranylphenols Promoted by Phosphite-Urea Cooperative Catalysts
  作者：Yasuhiro Sawamura、Hidefumi Nakatsuji、Matsujiro Akakura、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1002/chir.22297

  日期：2014.7

  Nucleophilic phosphite–urea cooperative catalysts are highly efficient for the bromonium‐induced cyclization of 2‐geranylphenols. Phosphite–N,N’‐dimethylurea catalysts also show moderate activity, probably due to the steric effect of their bent conformation. Chirality 26:355–359, 2014. © 2014 Wiley Periodicals, Inc.

  亲核性亚磷酸酯-尿素协同催化剂对于溴诱导的2-香叶基苯酚的环化反应非常有效。亚磷酸-N，N'-二甲基脲催化剂也显示出中等活性，这可能是由于其弯曲构象的空间效应所致。手征性：2014年，26：355–359。©2014 Wiley Periodicals，Inc.