methyl 3,7-dimethylphenanthrene-9-carboxylate | 1436427-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: methyl 3,7-dimethylphenanthrene-9-carboxylate
• CAS: 1436427-38-1
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: VPGFLTGBZDZFOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2'-(3-methoxy-3-oxoprop-1-en-1-yl)-4,5'-dimethyl-[1,1'-biphenyl]-2-carboxylic acid 在 N-碘代丁二酰亚胺 、 potassium carbonate 作用下， 反应 12.0h， 以64%的产率得到methyl 3,7-dimethylphenanthrene-9-carboxylate
  参考文献：
  名称：

  Remote and Selective C(sp²)–H Olefination for Sequential Regioselective Linkage of Phenanthrenes

  摘要：

  Biphenylcarboxylic acid with two competing C(sp(2))-H sites was designed for site selective C(sp(2))-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.

  DOI：

  10.1021/acs.orglett.0c01208

文献信息

• Phenanthrene Synthesis by Eosin Y-Catalyzed, Visible Light- Induced [4+2] Benzannulation of Biaryldiazonium Salts with Alkynes
  作者：Tiebo Xiao、Xichang Dong、Yanchi Tang、Lei Zhou

  DOI：10.1002/adsc.201200569

  日期：2012.11.26

  A metal-free, visible light-induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9-substituted or 9,10-disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence.

  开发了一种无金属，可见光诱导的联炔重氮盐与炔烃的[4 + 2]苯环。以曙红Y为光氧化还原催化剂，通过级联自由基加成和环化顺序获得了多种9-取代或9,10-二取代的菲。