1-indanylphenylcarbinol | 146393-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-indanylphenylcarbinol
• 英文别名: Indan-1-yl-phenyl-methanol；1-(α-Oxy-benzyl)-hydrinden；2,3-dihydro-1H-inden-1-yl(phenyl)methanol
• CAS: 146393-32-0
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: UGAWJCQOQFOFSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-indanylphenylcarbinol 、 碘甲烷 在 正丁基锂 作用下， 生成 (1S,αS,1R,αR)-1-(α-methoxybenzyl)indan 、 (1S,αS,1R,αR)-1-(α-methoxybenzyl)indan
  参考文献：
  名称：

  Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol

  摘要：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

  DOI：

  10.1021/jo00007a033
• 作为产物：
  描述：

  3-(α-oxy-benzyl)-indene 在 乙醚 、 铂 作用下， 生成 1-indanylphenylcarbinol
  参考文献：
  名称：

  Vertebral Artery Dissection and Migraine Headaches in Children

  摘要：

  后循环中风在儿童中并不常见。在椎基底动脉损害中，椎动脉夹层仍然是一种罕见的诊断。我们报告了一例8岁男孩的病例，患有偏头痛症状，出现了急性小脑体征和激动，之后出现了双侧小脑半球多次梗死。椎动脉造影显示左侧椎动脉夹层，基底动脉在其起始部位稍远处被闭塞。回顾了椎动脉夹层的风险因素，重点强调与偏头痛的关联。还介绍了用于诊断夹层的影像学研究。这个病例显示了在儿童患有不典型偏头痛且出现新的神经学表现时，考虑动脉壁夹层的重要性。

  DOI：

  10.1177/088307380001501011

文献信息

• Palladium‐Catalyzed Ring‐Opening Diarylation of Cyclobutanols for the Synthesis of Acylindanes
  作者：Wen‐Jing Yan、Hai‐Yong Tu、Zhiyong Liao、Xiao‐Qin Shen、Xing‐Guo Zhang

  DOI：10.1002/adsc.202300355

  日期：2023.7.4

  A method for the construction of the indane skeleton through palladium-catalyzed ring-opening diarylation of Cyclobutanols with aryl 1,2-dihalides has been described. The ring-expansion reaction involves β-carbon elimination of Cyclobutanols and subsequent α-carbon arylation of ketone to give 2-acylindanes in 42–93% yields.

  描述了通过钯催化环丁醇与芳基 1,2-二卤化物的开环二芳基化来构建茚满骨架的方法。扩环反应涉及环丁醇的 β-碳消除以及随后酮的 α-碳芳基化，得到 2-酰基茚满，产率 42-93%。