phenyl phenanthrene-9-carboxylate | 102184-00-9

• 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: phenyl phenanthrene-9-carboxylate
• 英文别名: phenyl 9-phenanthroate；phenanthrene-9-carboxylic acid phenyl ester；Phenanthren-9-carbonsaeure-phenylester
• CAS: 102184-00-9
• 化学式: C₂₁H₁₄O₂
• 分子量: 298.341
• InChiKey: FBHCVPVTARBUFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl phenanthrene-9-carboxylate 在 四氯化碳 、 lithium aluminium tetrahydride 、 乙醚 、 溴 、 苯 作用下， 生成 phenylindenophenanthrene
  参考文献：
  名称：

  1,4-Addition of Grignard Reagents to 9-Phenanthryl Ketones¹

  摘要：

  DOI：

  10.1021/ja01567a074
• 作为产物：
  描述：

  苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 N-乙酰-L-丙氨酸 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 silver carbonate 、 对苯醌 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 30.0h， 生成 phenyl phenanthrene-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

• DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID
  申请人：Alabugin Igor

  公开号：US20110237798A1

  公开（公告）日：2011-09-29

  A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.

  提供了一种制备芳香羧酸芳基酯或N-芳基芳香羧酰胺的方法。该方法包括将O,O-二芳基硫代碳酸酯或O-芳基-N-芳基硫代氨基甲酸酯与能够选择性地与硫反应的试剂接触，这种接触导致O-新叶基重排，从而分别形成芳香羧酸芳基酯或N-芳基芳香羧酰胺。
• Radical O→C Transposition: A Metal-Free Process for Conversion of Phenols into Benzoates and Benzamides
  作者：Abdulkader Baroudi、Jeremiah Alicea、Phillip Flack、Jason Kirincich、Igor V. Alabugin

  DOI：10.1021/jo102467j

  日期：2011.3.18

  We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the C═S moiety. This addition step, analogous to the first step of the Barton−McCombie reaction, produces a carbon radical

  我们报告了通过新的自由基级联将苯酚转化为苯甲酸的酯和酰胺的无金属方法。二芳基硫代碳酸酯和硫代氨基甲酸酯可在单个高产率步骤中从苯酚获得，可在C═S部分的硫原子上选择性添加甲硅烷基。该添加步骤类似于Barton-McCombie反应的第一步，产生的碳原子团通过O进行1,2 O→C换位-新叶重排。可逆重排步骤中通常不利的平衡是通过O中心自由基中的高放热C-S键断裂而向前移动的，这提供了最终的苯甲酸酯或苯甲酰胺产品。由苯酚的无金属苯甲酸衍生物的制备为芳基三氟甲磺酸酯的金属催化的羰基化提供了潜在有用的替代方法。
• US8410303B2
  申请人：——

  公开号：US8410303B2

  公开（公告）日：2013-04-02
• Remote and Selective C(sp²)–H Olefination for Sequential Regioselective Linkage of Phenanthrenes
  作者：Yi Wei、Abing Duan、Pan-Ting Tang、Jia-Wei Li、Rou-Ming Peng、Zheng-Xin Zhou、Xiao-Peng Luo、Mohamedally Kurmoo、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1021/acs.orglett.0c01208

  日期：2020.6.5

  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.
• 1,4-Addition of Grignard Reagents to 9-Phenanthryl Ketones¹
  作者：Reynold C. Fuson、Stanley J. Strycker

  DOI：10.1021/ja01567a074

  日期：1957.5