1-(2-碘乙基)-4-(三氟甲基)苯 | 178685-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-碘乙基)-4-(三氟甲基)苯
• 中文别名: 4-(2-碘乙基)三氟甲苯
• 英文名称: 1-(2-iodoethyl)-4-(trifluoromethyl)benzene
• 英文别名: 4-(2-Iodoethyl)benzotrifluoride
• CAS: 178685-14-8
• 化学式: C₉H₈F₃I
• 分子量: 300.062
• InChiKey: SRZXEFNIPPUVHS-UHFFFAOYSA-N

物化性质

• 沸点：
  246.1±40.0 °C(Predicted)
• 密度：
  1.718±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-碘乙基)-4-(三氟甲基)苯 在 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 (1R,4S,5R,8S,9R,12R,13R)-1,5-dimethyl-9-[3-[4-(trifluoromethyl)phenyl]propyl]-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
  参考文献：
  名称：

  Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates

  摘要：

  On the basis of earlier reported quantitative structure-activity relationship studies, a series of 9beta-16-(arylalkyl)-10-deoxoartemisinins were proposed for synthesis. Several of the new compounds 7 and 10-14 were synthesized, employing the key synthetic intermediate 23. In a second approach, the natural product (+)-artemisinic acid was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogues. Under a new approach, we developed A one step reaction for the interconversion of artemisinin 1 into artemisitene 22 that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of 22 in good yield. The lactone carbonyls, were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF3-etherate/Et3SiH) to afford the desired corresponding pyrans. Six additional halogen-substituted aromatic side chains were installed via 22 furnishing the bioassay candidates 15-20. The analogues were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were additionally tested. in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity, Of these, two were chosen for pharmacokinetic evaluation, 14 and 17.

  DOI：

  10.1021/jm020142z
• 作为产物：
  描述：

  4-(三氟甲基)苯乙醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-碘乙基)-4-(三氟甲基)苯
  参考文献：
  名称：

  2-取代的（2SR）-2-氨基-2-（（（1SR，2SR）-2-羧基环丙-1-基）甘氨酸作为II类代谢型谷氨酸受体的有效和选择性拮抗剂。2.芳族取代，药理学表征和生物利用度的影响。

  摘要：

  在本文中，我们描述了一系列有效的和选择性的II型代谢型谷氨酸受体（mGluR）激动剂（1S，1'S，2'S）-羧基环丙基甘氨酸（2，L-CCG 1）的一系列α-取代类似物的合成。在氨基酸碳上引入取代基将激动剂2转化为拮抗剂。所有化合物均已制备并测试为一系列四个异构体，即两个外消旋非对映异构体。基于对α-苯乙基类似物3亲和力的改善，在本文中，我们探讨了取代对芳环的影响，作为增加与这些化合物对II型mGluRs的亲和力的策略。II组mGluRs的亲和力是使用[3H]谷氨酸（Glu）在大鼠前脑膜中的结合来测量的。通过测量它们在人类mGluR2和mGluR3转染的RGT细胞中拮抗（1S，3R）-1-氨基环戊烷-1,3-二羧酸诱导的福司柯林刺激的环-AMP抑制作用的能力，证实了它们的拮抗活性。3的芳香环上的间位取代基由各种取代基提供，这些取代基分别是给电子（例如甲基，羟基，氨基，甲氧基，苯基，苯氧基

  DOI：

  10.1021/jm970498o

文献信息

• [EN] ARTEMISININ-BASED PEROXIDE COMPOUNDS AS BROAD SPECTRUM ANTI-INFECTIVE AGENTS<br/>[FR] COMPOSES DE PEROXYDE A BASE D'ARTEMISININE TENANT LIEU D'AGENTS ANTI-INFECTIEUX A LARGE SPECTRE
  申请人：UNIV MISSISSIPI

  公开号：WO2003095444A1

  公开（公告）日：2003-11-20

  Described herein is the synthesis, bioassay results and utility of new C-9 and C-10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文描述了合成、生物测定结果以及新的C-9和C-10取代青蒿素衍生物的用途，这些衍生物具有易于功能化的基团，通过碳链或杂原子连接到青蒿素骨架上。同时还展示了这类化合物在广谱抗寄生虫活性方面的表现。其中一些类似物具有明显的细胞毒性，专门用于治疗癌症性疾病。
• Unprecedented copper-mediated oxidative demethylation of propionamides via bidentate-chelation assistance
  作者：Jing-Hui Liu、Mian Cui、Xiao-Yu Lu、Zhen-Qi Zhang、Bin Xiao、Yao Fu

  DOI：10.1039/c5cc08393a

  日期：——

  The copper-mediated bidentate-chelation directing group assisted oxidative demethylation of substituted propionamides was developed for the first time.

  首次开发了铜介导的双齿螯合定向基辅助的取代丙酰胺的氧化去甲基化反应。
• Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution
  作者：Masahiro Kojima、Shigeki Matsunaga、Tomoyuki Sekino、Shunta Sato、Kazuki Kuwabara、Koji Takizawa、Tatsuhiko Yoshino

  DOI：10.1055/s-0040-1707524

  日期：2020.7

  rare 1,1-dipole synthons, allyl sulfones are rarely used in target-oriented syntheses, likely due to the lack of a general catalytic method for their branch-selective allylic substitution. Herein, we identified allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated α-derivatization and subsequent cobalt-catalyzed allylic substitution. The sequential transformations allow for highly

  尽管烯丙基砜具有罕见的1,1-偶极合成子的独特潜力，但很少用于目标导向的合成中，这可能是由于缺乏用于支链选择性烯丙基取代的通用催化方法。在这里，我们确定了烯丙基4-氯苯基砜作为通用介导的碱介导的α-衍生化和随后的钴催化的烯丙基取代。连续转化允许高度区域选择性地获得具有多种脂族侧链的支链烯丙基取代产物。与传统的金属催化方案相比，光氧化还原使能的钴催化对于实现高产率和区域选择性的脱磺酰基取代是必不可少的，而传统的金属催化方案在相应的转化中导致了较差的结果。
• [EN] EXCITATORY AMINO ACID RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RECEPTEURS D'ACIDES AMINES EXCITATEURS
  申请人：ELI LILLY AND COMPANY

  公开号：WO1996007405A1

  公开（公告）日：1996-03-14

  (EN) The present invention provides compounds of formula (I) in which R is as defined in the specification, or a pharmaceutically acceptable metabolically labile ester or amide thereof, or a pharmaceutically acceptable salt thereof, which are useful as antagonists of one or more of the actions of L-glutamate at metabotropic excitatory amino acid receptors.(FR) Cette invention concerne des composés de formule (I), dans laquelle R est tel que défini dans le descriptif, ou un ester ou amide pharmaceutiquement acceptable de ces composés qui est métaboliquement labile, ou encore un sel pharmaceutiquement acceptable de ces composés, qu'on utilise comme antagonistes d'une ou de plusieurs actions du L-glutamate au niveau des récepteurs d'acides aminés excitateurs métabotropiques.

  本发明提供了公式（I）的化合物，其中R如规范中定义，或其药物可接受的代谢易裂解酯或酰胺，或其药物可接受的盐，这些化合物是L-谷氨酸在代谢型兴奋性氨基酸受体上的一个或多个作用的拮抗剂。
• Artemisinin-based peroxide compounds as broad spectrum anti-infective agents
  申请人：Avery Mitchell

  公开号：US20050240034A1

  公开（公告）日：2005-10-27

  Described herein is the synthesis, bioassay results and utility of new C- 9 and C- 10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文介绍了一种新型C-9和C-10取代青蒿素衍生物的合成、生物测定结果和实用性，这些衍生物通过碳链或杂原子与青蒿素骨架连接，具有易于官能团化的基团。同时，本文还展示了这类化合物的广谱抗寄生虫活性。其中某些类似物具有明显的细胞毒性，可用于治疗癌症疾病。