(m-tolyl)-(3,5-dimethoxy-phenyl)-methanone | 1046145-53-2

• 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: (m-tolyl)-(3,5-dimethoxy-phenyl)-methanone
• 英文别名: (3,5-dimethoxyphenyl)(m-tolyl)methanone；(3,5-Dimethoxyphenyl)-(3-methylphenyl)methanone；(3,5-dimethoxyphenyl)-(3-methylphenyl)methanone
• CAS: 1046145-53-2
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD20041075
• 分子量: 256.301
• InChiKey: CJRNKGZYSMABDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  (m-tolyl)-(3,5-dimethoxy-phenyl)-methanone 、 Dimethylzinc 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75.3%的产率得到1-[1-(m-tolyl)-1-methyl-ethyl]-3,5-dimethoxy-benzene
  参考文献：
  名称：

  Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

  摘要：

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.034
• 作为产物：
  描述：

  间苯二甲醚 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 [Pd(IPr)(cin)Cl] 、 potassium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 40.0h， 生成 (m-tolyl)-(3,5-dimethoxy-phenyl)-methanone
  参考文献：
  名称：

  通过Ir催化的CH硼化/ NC（O）活化，酰胺的选择性和发散性不同的酰胺和芳基交叉偶联。

  摘要：

  在这里，我们证明酰胺可以通过连续的Ir催化的C–H硼酸酯化/ N–C（O）活化而容易地与未活化的芳烃偶联。这种方法可通过空间控制的Ir催化的C–H硼化以及不同的酰基和脱羰基酰胺N–C（O）和C–C活化来轻松获得联芳基酮和联芳基。该方法转移了传统的酰化和芳基化区域选择性，使我们能够直接利用容易获得的芳烃和酰胺来产生有价值的酮和联芳基。

  DOI：

  10.1021/acs.orglett.0c02105

文献信息

• Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis
  作者：Renhe Li、Feipeng Liu、Guangbin Dong

  DOI：10.1016/j.chempr.2019.02.005

  日期：2019.4

  cooperative catalysis, also known as the Catellani reaction, has become an increasingly useful method for site-selective arene functionalization; however, certain constraints still exist because of its intrinsic mechanistic pathway. Herein, we report a redox-neutral ortho functionalization of aryl boroxines via Pd/NBE catalysis. An electrophile, such as carboxylic acid anhydrides or O-benzoyl hydroxylamines,

  钯/降冰片烯（Pd / NBE）协同催化，也称为Catellani反应，已成为位点选择性芳烃官能化的一种越来越有用的方法。但是，由于其固有的机理途径，仍然存在某些限制。在这里，我们报告通过Pd / NBE催化的芳基硼氧烷的氧化还原中性邻位官能化。亲电子试剂，例如羧酸酐或O-苯甲酰基羟胺，在环硼氧烷邻位偶联，质子作为第二种亲电子试剂引入ipso位置。该反应不需要额外的氧化剂或还原剂，并且避免了化学计量的碱或酸，从而可以耐受各种官能团。特别地，证明了芳基碘和环硼氧烷部分之间的正交化学选择性，其可用于控制反应序列。最后，氘标记研究支持ipso质子化途径。这种独特的机械特性可能会激发新型Pd / NBE催化的转化的发展。
• Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C–H Borylation/N–C(O) Activation
  作者：Pengcheng Gao、Michal Szostak

  DOI：10.1021/acs.orglett.0c02105

  日期：2020.8.7

  Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C–H borylation/N–C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C–H borylation and divergent acyl and decarbonylative amide N–C(O) and C–C activation. The methodology diverts the traditional acylation and arylation

  在这里，我们证明酰胺可以通过连续的Ir催化的C–H硼酸酯化/ N–C（O）活化而容易地与未活化的芳烃偶联。这种方法可通过空间控制的Ir催化的C–H硼化以及不同的酰基和脱羰基酰胺N–C（O）和C–C活化来轻松获得联芳基酮和联芳基。该方法转移了传统的酰化和芳基化区域选择性，使我们能够直接利用容易获得的芳烃和酰胺来产生有价值的酮和联芳基。
• Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs
  作者：Mathangi Krishnamurthy、Steven Gurley、Bob M. Moore II

  DOI：10.1016/j.bmc.2008.05.034

  日期：2008.7.1

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.