2-(2-bromo-3,5-dimethoxyphenyl)acetonitrile | 921930-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-bromo-3,5-dimethoxyphenyl)acetonitrile
• 英文别名: 2-(2-Bromo-3,5-dimethoxyphenyl)acetonitrile
• CAS: 921930-95-2
• 化学式: C₁₀H₁₀BrNO₂
• 分子量: 256.099
• InChiKey: PVWXVBSBSRGCFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  365.4±37.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-3,5-dimethoxyphenyl)acetonitrile 在 sodium hydroxide 、 4 A molecular sieve 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (+-)-5-(2-bromo-3,5-dimethoxybenzyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
  参考文献：
  名称：

  Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.

  摘要：

  Three new alkaloids (1-3) and twenty-one known compounds were isolated from the stem of Fissistigma oldhamii (Hemsl.) Merr. which was the ruler herb in an approved Traditional Chinese herbal formula used for treatment of rheumatoid arthritis in China and synthesis of one new immunosuppressive alkaloid was achieved. These compounds, including the crude extracts of this herb, exhibited strong activities in the inhibition of T and B cell proliferation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.034
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2-bromo-3,5-dimethoxyphenyl)acetonitrile
  参考文献：
  名称：

  Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.

  摘要：

  Three new alkaloids (1-3) and twenty-one known compounds were isolated from the stem of Fissistigma oldhamii (Hemsl.) Merr. which was the ruler herb in an approved Traditional Chinese herbal formula used for treatment of rheumatoid arthritis in China and synthesis of one new immunosuppressive alkaloid was achieved. These compounds, including the crude extracts of this herb, exhibited strong activities in the inhibition of T and B cell proliferation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.034

文献信息

• Site‐Selective C–C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis
  作者：Jing‐Hong Guo、Yu Liu、Xin‐Cheng Lin、Tian‐Mu Tang、Bi‐Qin Wang、Ping Hu、Ke‐Qing Zhao、Feijie Song、Zhang‐Jie Shi

  DOI：10.1002/anie.202106709

  日期：2021.8.23

  Controlling the chemo- and regioselectivity of transition-metal-catalyzed C−C activation remains a great challenge. The transformations of benzocyclobutenones (BCBs) usually involve the cleavage of C1−C2 bond. In this work, an unprecedented highly selective cleavage of C1−C8 bond with the insertion of alkynes is achieved by using blocking strategy via Ni catalysis, providing an efficient method for

  控制过渡金属催化的 C-C 活化的化学和区域选择性仍然是一个巨大的挑战。苯并环丁烯酮 (BCB) 的转化通常涉及 C1-C2 键的断裂。在这项工作中，通过 Ni 催化使用封闭策略实现了前所未有的 C1-C8 键的高选择性裂解和炔烃的插入，为合成 1,8-二取代萘提供了一种有效的方法。值得注意的是，转化后可以很容易地去除封闭基团。
• Chemoselective Ullmann coupling at room temperature: a facile access to 2-aminobenzo[b]thiophenes
  作者：Manojkumar Janni、Annaram Thirupathi、Sahil Arora、S. Peruncheralathan

  DOI：10.1039/c7cc03273k

  日期：——

  Various functionalized 2-aminobenzo[b]thiophenes have been synthesized at room temperature by the Ullmann coupling reaction for the first time. The enantiospecific coupling reaction has been further demonstrated without loss of optical purity. The newly synthesized 2-anilino-3-cyano-benzo[b]thiophenes are transformed into 11-amino-benzothieno[2,3-b]quinolines in the presence of triflic acid.

  各种官能化的2-氨基苯并[ b ]噻吩在室温下首次通过乌尔曼偶合反应合成。已经进一步证明了对映特异性偶联反应，而没有光学纯度的损失。在三氟甲磺酸存在下，将新合成的2-苯胺基-3-氰基-苯并[ b ]噻吩转化为11-氨基-苯并噻吩并[2，3- b ]喹啉。
• Copper Catalyzed Intramolecular N-Arylation of Ketene Aminals at Room Temperature: Synthesis of 2-Amino-3-cyanoindoles
  作者：Annaram Thirupathi、Manojkumar Janni、Saravanan Peruncheralathan

  DOI：10.1021/acs.joc.8b00816

  日期：2018.8.3

  Various 2-amino-3-cyanoindoles are synthesized through copper catalyzed intramolecular N-arylations of ketene aminals at room temperature for the first time with 60–99% yields within 0.1–2 h. Controlled regioselective N-arylations of unsymmetrical ketene aminals are also studied. Further, a new double heteroannulation approach is demonstrated for the synthesis of 11-aminoindolo[2,3-b]quinolines from

  在室温下首次通过铜催化乙烯酮缩醛的分子内N-芳基化反应合成了各种2-氨基-3-氰基吲哚，其收率在0.1-2 h内达到60-99％。还研究了不对称乙烯酮缩醛的可控区域选择性N-芳基化。此外，从非环和非杂环的前体合成11-氨基吲哚并[2,3- b ]喹啉的新的双异环的方法被证明。
• Total Synthesis of Laetevirenol A
  作者：Young Lok Choi、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1021/jo301345a

  日期：2012.10.5

  The first complete synthesis of laetevirenol A was performed in nine steps via intramolecular Friedel–Crafts alkylation in a trans-selective manner. The key phenanthrene intermediate was synthesized by a one-pot Suzuki–Miyaura coupling and an aldol condensation cascade reaction.

  Laetevirenol A的第一个完整合成是通过分子内Friedel-Crafts烷基化反应以反选择方式在9个步骤中完成的。关键的菲中间体是通过一锅Suzuki-Miyaura偶联和醛醇缩合级联反应合成的。
• Synthesis of the Core Tricyclic Ring Domain of (−)-Schulzeine B
  作者：Naoyuki Hoshiya、Kenta Noda、Yuji Mihara、Nobuyuki Kawai、Jun’ichi Uenishi

  DOI：10.1021/acs.joc.5b01173

  日期：2015.8.7

  A formal synthesis of (−)-schulzeine B, a marine natural alkaloid possessing potent antidiabetic activity, has been achieved. A benzo[a]quinolizidin-4-one is a common skeleton of schulzeines (A–C). (−)-Schulzeine B possesses an (S)-stereogenic center at the C-3 carbon. The chiral (3S,11bS)-3-amino-9,11-dimethoxybenzo[a]quinolizidin-4-one has been prepared efficiently from (2-bromo-3,5-dihydroxyphenyl)acetonitrile

  已完成（-）-schulzeine B（一种具有强大的抗糖尿病活性的海洋天然生物碱）的正式合成。苯并[ a ]喹啉齐丁-4-酮是舒尔西因（A–C）的常见骨架。（-）-舒尔西丁B在C-3碳上具有（S）-立体异构中心。由（2-溴-3,5-二羟基苯基）乙腈分17步有效地制备了手性（3 S，11b S）-3-氨基-9,11-二甲氧基苯并[ a ]喹啉亚丁-4-一）由HClO 4催化的脱水分子内胺化；和（ii）脯氨酸或硼酸催化的反式环酰胺化反应，用于构建δ-内酰胺环。