furfuryl 2,2,2-trichloroacetimidate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: furfuryl 2,2,2-trichloroacetimidate
• 英文别名: Furfuryl trichloroacetimidate；furan-2-ylmethyl 2,2,2-trichloroethanimidate
• 化学式: C₇H₆Cl₃NO₂
• 分子量: 242.489
• InChiKey: RLEXZYXRRNMBGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  furfuryl 2,2,2-trichloroacetimidate 、 1-苯基-5-巯基四氮唑 以 四氢呋喃 为溶剂， 以69%的产率得到5-[(2-furanylmethyl)thio]-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Alkylation of thiols with trichloroacetimidates under neutral conditions

  摘要：

  Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.042
• 作为产物：
  描述：

  糠醇 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以99%的产率得到furfuryl 2,2,2-trichloroacetimidate
  参考文献：
  名称：

  Alkylation of thiols with trichloroacetimidates under neutral conditions

  摘要：

  Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.042

文献信息

• Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
  作者：Nivedita S. Mahajani、Rowan I. L. Meador、Tomas J. Smith、Sarah E. Canarelli、Arijit A. Adhikari、Jigisha P. Shah、Christopher M. Russo、Daniel R. Wallach、Kyle T. Howard、Alexandra M. Millimaci、John D. Chisholm

  DOI：10.1021/acs.joc.9b00745

  日期：2019.6.21

  Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive

  三氯乙亚氨酸酯是在温和条件下合成酯的有用试剂，不需要外源促进剂。这些条件避免了带有敏感官能团的底物发生不希望的分解，这种分解通常在使用强路易斯酸或布朗斯台德酸的情况下观察到。通过加热，这些反应已扩展为不具有给电子基团的苄基酯。这些廉价且方便的方法应在复杂基质中酯的形成中找到应用。
• D-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and
  申请人：Merck & Co., Inc.

  公开号：US05252732A1

  公开（公告）日：1993-10-12

  O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides of the general structural Formula I: ##STR1## have been prepared from suitable precursors by alkylation and/or arylation at C-3" and/or C-4" of the cyclohexyl ring. These macrolide immunosuppressants are useful in a mammalian host for the treatment of autoimmune diseases, infectious diseases, the prevention of rejection of foreign organ transplants and/or related afflictions, diseases and illnesses.

  通式I的O-杂环芳基、O-烷基杂环芳基、O-烯基杂环芳基和O-炔基杂环芳基大环内酯，可通过在环己基环上的C-3"和/或C-4"处进行烷基化和/或芳基化反应，从适当的前体制备而成。这些大环内酯免疫抑制剂在哺乳动物宿主中用于治疗自身免疫性疾病、传染病、预防外来器官移植的排斥和/或相关的疾病、病症。
• O-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and
  申请人：Merck & Co., Inc.

  公开号：US05349061A1

  公开（公告）日：1994-09-20

  O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroaryl-macrolides of the general structural Formula I: ##STR1## have been prepared from suitable precursors by alkylation and/or arylation at C-3" and/or C-4" of the cyclohexyl ring. These macrolide immunosuppressants are useful in a mammalian host for the treatment of autoimmune diseases, infectious diseases, the prevention of rejection of foreign organ transplants and/or related afflictions, diseases and illnesses.

  通式I的O-杂环芳基、O-烷基杂环芳基、O-烯基杂环芳基和O-炔基杂环芳基大环内酯已通过在环己烷环的C-3"和/或C-4"处进行烷基化和/或芳基化反应制备。这些大环内酯免疫抑制剂在哺乳动物宿主中用于治疗自身免疫性疾病、传染病、预防外源性器官移植排斥及/或相关的疾病和疾病。