3-bromo-2,5-dimethylfuran

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-2,5-dimethylfuran
• 英文别名: 2,5-dimethyl-3-bromofuran
• 化学式: C₆H₇BrO
• 分子量: 175.025
• InChiKey: IRVMQYYRGICZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2,5-dimethylfuran 在 copper(l) iodide 、 四(三苯基膦)钯 、 四甲基乙二胺 、 对甲苯磺酸 、 三苯基膦 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 80.0~125.0 ℃ 、3.04 MPa 条件下， 反应 32.0h， 生成 3-(2,5-dimethylfuran-3-yl)-4-(2,5-dimethylthiophen-3-yl)-1-(4-methoxyphenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Palladium-Catalyzed Aminocarbonylation of Alkynes to Succinimides

  摘要：

  Succinimide derivatives are useful building blocks for the synthesis of natural products and drugs. We describe an efficient route to succinimide derivatives comprising Pd(xantphos)Cl2-catalyzed aminocarbonylation of alkynes with aromatic or aliphatic amines in the presence of p-TsOH. The utility of this route is demonstrated with the synthesis of a large number of succinimide compounds including an important photochromic molecule.

  DOI：

  10.1021/jo502412v
• 作为产物：
  描述：

  2,5-二甲基呋喃 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 3.0h， 以67%的产率得到3-bromo-2,5-dimethylfuran
  参考文献：
  名称：

  Palladium-Catalyzed Aminocarbonylation of Alkynes to Succinimides

  摘要：

  Succinimide derivatives are useful building blocks for the synthesis of natural products and drugs. We describe an efficient route to succinimide derivatives comprising Pd(xantphos)Cl2-catalyzed aminocarbonylation of alkynes with aromatic or aliphatic amines in the presence of p-TsOH. The utility of this route is demonstrated with the synthesis of a large number of succinimide compounds including an important photochromic molecule.

  DOI：

  10.1021/jo502412v

文献信息

• Photochromic and fluorescent properties of bisfurylethene derivatives
  作者：Tadatsugu Yamaguchi、Masahiro Irie

  DOI：10.1039/b611294c

  日期：——

  Photochromic diarylethenes having furan units (1 and 3) were synthesized and their photochromic performances were compared with those having thiophene units. The cyclization quantum yields of both derivatives in hexane are similar. In contrast, the cycloreversion quantum yield of the derivative having furan units (1) is much larger than that having thiophene units (2) in hexane. The difference is attributed to the conformation of the closed-ring isomers. Although 2a and 4a do not show any fluorescence, 1a and 3a exhibit fluorescence. Photochromism in the single crystalline phase was also observed for 1 and 3. Upon irradiation with 313 nm light, the colorless crystals 1 and 3 changed to violet and yellow, respectively.

  合成了具有呋喃单元（1 和 3）的光致变色二元乙烷，并将其光致变色性能与具有噻吩单元的二元乙烷进行了比较。这两种衍生物在己烷中的环化量子产率相似。相比之下，具有呋喃单元的衍生物（1）在正己烷中的环化量子产率要比具有噻吩单元的衍生物（2）大得多。这种差异归因于闭环异构体的构象。虽然 2a 和 4a 没有显示任何荧光，但 1a 和 3a 却显示了荧光。在单晶相中还观察到 1 和 3 的光致变色现象。在 313 纳米的光照射下，无色晶体 1 和 3 分别变为紫色和黄色。
• HETEROCYCLE -ARYL COMPOUNDS FOR INFLAMMATION AND IMMUNE-RELATED USES
  申请人：SYNTA PHARMACEUTICALS CORP.

  公开号：US20130236481A1

  公开（公告）日：2013-09-12

  The invention relates to compounds that are useful as immunosuppressive agents and for treating and preventing inflammatory conditions, allergic disorders, and immune disorders.

  本发明涉及到一类可用作免疫抑制剂的化合物，以及用于治疗和预防炎症状况、过敏性疾病和免疫疾病的化合物。
• HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20160009744A1

  公开（公告）日：2016-01-14

  Disclosed are chemical entities which are compounds of formula (I): or pharmaceutically acceptable salts thereof; wherein Y, R a , R a′ , R b , R c , X 1 , X 2 , X 3 , R d , Z 1 , and Z 2 have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry. Chemical entities according to the disclosure can be useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular, and neurodegenerative diseases or disorders.

  本发明涉及化学实体，其为以下式（I）的化合物或其药学上可接受的盐；其中，Y、Ra、Ra′、Rb、Rc、X1、X2、X3、Rd、Z1和Z2具有本文所述的值，并在星号位置描绘的立体化学构型表示绝对立体化学。根据本发明的化学实体可用作Sumo激活酶（SAE）的抑制剂。进一步提供了包括本发明化合物的制药组合物以及使用这些组合物治疗增生性、炎症性、心血管和神经退行性疾病或疾患的方法。
• Froehlich, J., Bulletin des Societes Chimiques Belges, 1996, vol. 105, # 10-11, p. 615 - 634
  作者：Froehlich, J.

  DOI：——

  日期：——
• Synthesis of trisubstituted furans from 2-bromo-5-methylfuranvia halogen migrations and their selective preventions
  作者：J. Fr�hlich、C. Hametner

  DOI：10.1007/bf00810886

  日期：1996.4

  New trisubstituted furans exhibiting two different substitution patterns were synthesized via lithiation of 2-bromo-5-methylfuran. Choice of appropriate reaction parameters enabled selective halogen dance reactions, affording 2-substituted 3-bromo-5-methylfurans upon quenching with various electrophiles. Moreover, from the same starting material also complete prevention of halogen migration could be achieved, thus providing selective access to 3-substituted 2-bromo-5-methylfurans.

表征谱图