3-(allyloxy)-6H-benzo[c]chromen-6-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(allyloxy)-6H-benzo[c]chromen-6-one
• 英文别名: 3-Prop-2-enoxybenzo[c]chromen-6-one
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: DBMGMNPNPGOWGY-UHFFFAOYSA-N

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：
  0.06
• 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：

  3-(allyloxy)-6H-benzo[c]chromen-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到4-(allyloxy)-2'-(hydroxymethyl)[1,1'-biphenyl]-2-ol
  参考文献：
  名称：

  酯酶可裂解的过硫化物供体，无亲电副产物和荧光报告基团

  摘要：

  硫化氢 (H 2 S) 和相关的硫物质（称为过硫化物或硫烷硫）被认为是氧化应激的第一反应者。然而，能够可靠地生成这些物质而不产生任何潜在有毒副产品的工具是有限的，报告生成过硫化物的工具就更少了。在这里，我们使用嵌入N-乙酰半胱氨酸过硫化物的潜在荧光团，报告了一种新工具，该工具被酯酶裂解以产生过硫化物以及荧光报告基团，而没有任何亲电子副产物。荧光报道分子的形成速率几乎与过硫化物的形成速率相同，这表明使用该探针消除了报告过硫化物形成的二次测定的需要。新开发的供体具有过硫化物生成的症状，能够保护软骨细胞免受氧化应激。

  DOI：

  10.1039/d3cc04948e
• 作为产物：
  描述：

  4'-(allyloxy)-[1,1'-biphenyl]-2-carboxylic acid 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以66%的产率得到3-(allyloxy)-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Oxidant-Free C(sp²)–H Functionalization/C–O Bond Formation: A Kolbe Oxidative Cyclization Process

  摘要：

  An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H-2 being the only byproduct. A series of dibenzopyranones was obtained in good to excellent yields. Urolithins A, B, and C are formally synthesized by adopting this method as a key step to demonstrate its synthetic utility.

  DOI：

  10.1021/acs.joc.8b00089

文献信息

• Silver-Catalyzed C(sp²)–H Functionalization/C–O Cyclization Reaction at Room Temperature
  作者：Jian-Jun Dai、Wen-Tao Xu、Ya-Dong Wu、Wen-Man Zhang、Ying Gong、Xia-Ping He、Xin-Qing Zhang、Hua-Jian Xu

  DOI：10.1021/jo5024238

  日期：2015.1.16

  Silver-catalyzed C(sp(2))-H functionalization/CO cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)(2)S2O8 oxidant in CH2Cl2/H2O solvent, various lactones are obtained in good to excellent yields. A kinetic isotope effect (KIE) study indicates that the reaction may occur via a radical process.
• Oxidant-Free C(sp²)–H Functionalization/C–O Bond Formation: A Kolbe Oxidative Cyclization Process
  作者：Lei Zhang、Zhenxing Zhang、Junting Hong、Jian Yu、Jianning Zhang、Fanyang Mo

  DOI：10.1021/acs.joc.8b00089

  日期：2018.3.16

  An anodic oxidation/cyclization of 2-arylbenzoic acids for the synthesis of dibenzopyranones has been developed. The reaction proceeds at room temperature with no oxidant or electrolyte required and exhibits a high atom economy with H-2 being the only byproduct. A series of dibenzopyranones was obtained in good to excellent yields. Urolithins A, B, and C are formally synthesized by adopting this method as a key step to demonstrate its synthetic utility.
• An esterase-cleavable persulfide donor with no electrophilic byproducts and a fluorescence reporter
  作者：Bharat S. Choudhary、T. Anand Kumar、Akshi Vashishtha、Sushma Tejasri、Amal S. Kumar、Rachit Agarwal、Harinath Chakrapani

  DOI：10.1039/d3cc04948e

  日期：——

  a new tool that is cleaved by esterase to produce a persulfide as well as a fluorescence reporter without any electrophilic byproducts. The rate of formation of the fluorescence reporter is nearly identical to the rate of formation of the persulfide suggesting that the use of this probe eliminates the need for secondary assays that report persulfide formation. Symptomatic with persulfide generation

  硫化氢 (H 2 S) 和相关的硫物质（称为过硫化物或硫烷硫）被认为是氧化应激的第一反应者。然而，能够可靠地生成这些物质而不产生任何潜在有毒副产品的工具是有限的，报告生成过硫化物的工具就更少了。在这里，我们使用嵌入N-乙酰半胱氨酸过硫化物的潜在荧光团，报告了一种新工具，该工具被酯酶裂解以产生过硫化物以及荧光报告基团，而没有任何亲电子副产物。荧光报道分子的形成速率几乎与过硫化物的形成速率相同，这表明使用该探针消除了报告过硫化物形成的二次测定的需要。新开发的供体具有过硫化物生成的症状，能够保护软骨细胞免受氧化应激。