1-(2-bromo-4,5-methylenedioxyphenyl)-2-phenylethanone | 147437-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2-bromo-4,5-methylenedioxyphenyl)-2-phenylethanone
• 英文别名: 1-(6-Bromo-1,3-benzodioxol-5-yl)-2-phenylethanone；1-(6-bromo-1,3-benzodioxol-5-yl)-2-phenylethanone
• CAS: 147437-56-7
• 化学式: C₁₅H₁₁BrO₃
• 分子量: 319.155
• InChiKey: KKAVPDLDPIDQGH-UHFFFAOYSA-N

物化性质

• 沸点：
  456.5±45.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-4,5-methylenedioxyphenyl)-2-phenylethanone 在 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 8.5h， 生成 5,7-diphenyl-[1,3]dioxolo[4,5-g]quinolin-8(5H)-one
  参考文献：
  名称：

  Metal-Free Intramolecular Amination: One-Pot Tandem Synthesis of 3-Substituted 4-Quinolones

  摘要：

  3-Substituted 4-quinolones were synthesized using a one-pot metal-free strategy in moderate to quantitative yields. Carried out in dimethylsulfoxide (DMSO) via a sequential addition of materials, the methodology is tolerant of a wide range of functional groups and applicable to library synthesis.

  DOI：

  10.1021/co1000103
• 作为产物：
  描述：

  α-(2-bromo-4,5-methylenedioxyphenyl)-α-morpholinoacetonitrile 在 盐酸 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 1-(2-bromo-4,5-methylenedioxyphenyl)-2-phenylethanone
  参考文献：
  名称：

  Aidhen, Indrapal Singh; Narasimhan, N. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 211 - 221

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via <i>tert</i>-Butyl Isocyanide Insertion
  作者：Xiang-Dong Fei、Zhi-Yuan Ge、Ting Tang、Yong-Ming Zhu、Shun-Jun Ji

  DOI：10.1021/jo302004u

  日期：2012.11.16

  efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates

  已经开发了通过钯（0）-催化的结合叔丁基异氰化物的合成香豆素和邻苯二甲酸酯的新颖且高效的策略。该方法提供了合成这类有价值的内酯的最简单方法之一，涉及两个步骤，包括环化反应和简单的酸水解。该方法可耐受多种底物并适用于文库合成。
• New Method for the Synthesis of Lactones via Nickel-Catalyzed Isocyanides Insertion
  作者：Xiang-Dong Fei、Ting Tang、Zhi-Yuan Ge、Yong-Ming Zhu

  DOI：10.1080/00397911.2013.771402

  日期：2013.12.17

  novel nickel catalyst for the reaction of tert-butyl isocyanide insertion was discovered. In this approach, 1,2-bis(diphenylphosphino)ethane (L3) serves as an efficient ligand, thereby allowing the preparation of lactones from (o-bromophenyl)phenylethanone derivatives. It is noteworthy that this is the first example of nickel acting as a metal catalyst in the reactions of tert-butyl isocyanide insertion

  摘要 发现了一种用于叔丁基异氰化物插入反应的新型镍催化剂。在这种方法中，1,2-双（二苯基膦基）乙烷（L3）作为一种有效的配体，从而允许从（邻溴苯基）苯基乙酮衍生物制备内酯。值得注意的是，这是镍在叔丁基异氰化物插入反应中作为金属催化剂的第一个例子。这种方法的重要性可能会引起异氰化物掺入反应领域许多化学家的注意。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• A Novel Synthesis of Isoflavones via Copper(I)-Catalyzed Intramolecular Cyclization Reaction
  作者：Qiu-Lian Li、Qi-Lun Liu、Zhi-Yuan Ge、Yong-Ming Zhu

  DOI：10.1002/hlca.201000400

  日期：2011.7

  Isoflavone derivatives were synthesized via intramolecular cyclization of 3‐(2‐bromophenyl)‐3‐oxopropanal derivatives, using CuI as the catalyst, 2‐picolinic acid (=pyridine‐2‐carboxylic acid) as the ligand, K2CO3 as the base, and DMF as the solvent, in up to 96% yield. The synthesis is functional group‐tolerant.

  异黄酮衍生物是通过以CuI为催化剂，以2-吡啶甲酸（=吡啶-2-羧酸）为配体，以K 2 CO 3为催化剂，通过3-（2-溴苯基）-3-氧丙醛衍生物的分子内环化反应合成的。碱和DMF作为溶剂，产率高达96％。合成是官能团耐受的。
• Aidhen, Indrapal Singh; Narasimhan, N. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 211 - 221
  作者：Aidhen, Indrapal Singh、Narasimhan, N. S.

  DOI：——

  日期：——
• Metal-Free Intramolecular Amination: One-Pot Tandem Synthesis of 3-Substituted 4-Quinolones
  作者：Qi-Lun Liu、Qiu-Lian Li、Xiang-Dong Fei、Yong-Ming Zhu

  DOI：10.1021/co1000103

  日期：2011.1.10

  3-Substituted 4-quinolones were synthesized using a one-pot metal-free strategy in moderate to quantitative yields. Carried out in dimethylsulfoxide (DMSO) via a sequential addition of materials, the methodology is tolerant of a wide range of functional groups and applicable to library synthesis.