1-[(1,1-dimethyl-2-propynyl)oxy]-4-iodobenzene | 129180-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(1,1-dimethyl-2-propynyl)oxy]-4-iodobenzene
• 英文别名: 1-(1,1-dimethyl-2-propynyloxy)-4-iodobenzene；1-((1,1-Dimethyl-2-propynyl)oxy)-4-iodobenzene；1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene；1-iodo-4-(2-methylbut-3-yn-2-yloxy)benzene
• CAS: 129180-58-1
• 化学式: C₁₁H₁₁IO
• 分子量: 286.112
• InChiKey: HWARCJVQUDOHMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(1,1-dimethyl-2-propynyl)oxy]-4-iodobenzene 在 N,N-二乙基苯胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到2,2-dimethyl-6-iodo-2H-benzopyran
  参考文献：
  名称：

  Copper(I) Iodide: A Catalyst for the Improved Synthesis of Aryl Propargyl Ethers

  摘要：

  碘化铜（I）催化苯酚和二烷基丙炔酰氯之间的反应，生成芳基 1,1-二烷基丙炔醚 5a-k 和 7a-e，产量和纯度都很高。这些醚是 2H-1-苯并吡喃 8a-l 和 9a-e 的重要前体。

  DOI：

  10.1055/s-1995-3977
• 作为产物：
  描述：

  4-碘苯酚 、 methyl (2-methylbut-3-yn-2-yl)carbonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以86%的产率得到1-[(1,1-dimethyl-2-propynyl)oxy]-4-iodobenzene
  参考文献：
  名称：

  Improved synthesis of aryl 1,1-dimethylpropargyl ethers

  摘要：

  An efficient, general, and practical synthesis of aryl 1,1-dimethylpropargyl ethers has been developed.

  DOI：

  10.1016/s0040-4039(00)78231-1

文献信息

• Copper-Catalyzed Intramolecular Carbotrifluoromethylation of Alkynes for the Construction of Trifluoromethylated Heterocycles
  作者：Yanan Wang、Min Jiang、Jin-Tao Liu

  DOI：10.1002/chem.201404386

  日期：2014.11.17

  A mild and efficient copper‐catalyzed intramolecular carbotrifluoromethylation of alkynes has been achieved in the presence of Togni reagent as trifluoromethylating reagent. The reaction tolerates a range of substrates to give a group of trifluoromethylated heterocycles with high selectivities. A plausible mechanism was proposed on the basis of experimental results.

  在存在作为三氟甲基化试剂的Togni试剂的情况下，已实现了温和有效的铜催化炔烃分子内碳三氟甲基化反应。该反应容许一定范围的底物，以产生具有高选择性的一组三氟甲基化的杂环。根据实验结果提出了一个合理的机制。
• Phosphinic ester substituted benzopyran derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05612323A1

  公开（公告）日：1997-03-18

  ##STR1## and pharmaceutically acceptable salts thereof wherein Y is a single bond, --CH.sub.2 --, --C(O)--, --S-- or --N(R.sup.11)--; and R.sup.1 to R.sup.6 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

  其中Y为单键，--CH.sub.2 --，--C(O)--，--S--或--N(R.sup.11)--；R.sup.1至R.sup.6的定义如本文所述。这些化合物具有钾通道激活活性，因此例如可用作心血管药物。
• Pyranyl cyanoguanidine derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05140031A1

  公开（公告）日：1992-08-18

  Novel compounds having the formula ##STR1## wherein ##STR2## are disclosed. These compounds have potassium channel activating activity and are useful, for example, as cardiovascular agents, especially as antiischemic agents.

  揭示了具有以下化学式##STR1##的新化合物。这些化合物具有钾通道激活活性，例如作为心血管药物，特别是作为抗缺血药物时具有用途。
• Benzopyran derivatives and antihypertensive use thereof
  申请人：American Home Products Corporation

  公开号：US04908378A1

  公开（公告）日：1990-03-13

  Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.

  本文揭示了具有药理活性的新型苯并吡喃化合物，以及制备它们的方法、含有它们的药物组合物，以及它们在治疗高血压中的应用。
• Continuous Processing to Control a Potentially Hazardous Process:  Conversion of Aryl 1,1-Dimethylpropargyl Ethers to 2,2-Dimethylchromenes (2,2-Dimethyl-2<i>H</i>-1-Benzopyrans)
  作者：Ricardo J. Bogaert-Alvarez、Paul Demena、Gus Kodersha、Robert E. Polomski、N. Soundararajan、Steve S. Y. Wang

  DOI：10.1021/op0100504

  日期：2001.11.1

  The thermal Claisen rearrangement of 4-cyanophenyl 1,1-dimethylpropargyl ether (4) to 6-cyano-2,2-dimethylchromene (5), (6-eyano-2,2-dimethyl-2H-1-benzopyran), which is used in the synthesis of a potassium channel activator drug candidate, BMS-180448, created a significant process development issue. The resulting large heat release in this conversion posed not only a safety risk but could also cause product degradation if done in a batch-wise manner. The solution was to exploit the high surface-to-volume ratio of a plug-flow reactor that would maximize the heat transfer, thereby permitting tight and responsive temperature with better reaction control. In the course of successfully testing the plug-flow concept on "micro"-flow scale (gram quantity) and "kilo"-flow scale (similar to 10 kg), a generalized mathematical model capable of predicting the reaction performance based on the physical properties of any given plug-flow reactor was generated. The model provides requisite information to design and operate a plug-flow reactor of any size for this reaction. This model would optimize reaction conditions for an acquired reactor system capable of producing similar to7 kg/h of the dimethylchromene. Application of plug-flow reactor technology enabled production of high quality 2,2-dimethylchromenes in good yield (> 98 mol %) without the use of solvents and with virtually no waste streams.