4-(7-Hydroxy-3,5-diisopropyl-8,8-dimethyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-benzoic acid methyl ester | 84559-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(7-Hydroxy-3,5-diisopropyl-8,8-dimethyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-benzoic acid methyl ester
• CAS: 84559-62-6
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: YEWZRSNFNKAHRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl 4-(2,4,6-triisopropylbenzoyl)benzoate 以 solid 为溶剂， 反应 10.0h， 以54%的产率得到4-(7-Hydroxy-3,5-diisopropyl-8,8-dimethyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Structures and Photoreactivities of 2,4,6-Triisopropylbenzophenones

  摘要：

  测定了 2,4,6-三异丙基二苯甲酮（I）及其十种衍生物的晶体结构：(II) 2,4,6-三异丙基-3′-甲氧基二苯甲酮，(III) 3′-氯甲酰-2,4,6-三异丙基二苯甲酮，(IV) 3-（2,4、(V) 2,4,6-三异丙基-4′-甲基二苯甲酮， (VI) 4′-叔丁基-2,4,6-三异丙基二苯甲酮、(VII) 2,4,6-三异丙基-4′-甲氧基二苯甲酮， (VIII) 4-(2,4,6-三异丙基苯甲酰基)苯甲酸， (IX) 4′-氯甲酰-2,4、(X) 4-(2,4,6-三异丙基苯甲酰基)苯甲酸甲酯和 (XI) 4-(2,4,6-三异丙基苯甲酰基)苯甲酸乙酯。这些分子的构象基本相同。中心羰基与 3′-或 4′-取代的苯基近似共面，与三异丙基苯环垂直。(IX)和(X)在固态下的光稳定性归因于三异丙基苯基羰基的狭窄反应腔，即三异丙基苯基平面上的异丙基向羰基 C 原子的分子内运动受到分子间紧密接触的抑制。(IX)和(X)的光环化障碍之一是晶体中的π-π相互作用造成的二聚体结构，这是在苯环的 4′位上有极性甲氧基羰基或氯甲酰基团的结果。

  DOI：

  10.1107/s0108768198005515

文献信息

• Efficiency for solid-state photocyclization of 2,4,6-triisopropylbenzophenones
  作者：Yoshikatsu Ito、Teruo Matsuura、Keiichi Fukuyama

  DOI：10.1016/0040-4039(88)85092-5

  日期：1988.1

  Quantum yields for photocydization of 2,4,6-triisopropybenzophenones in the solid state were estimated by using an usual merry-go-round apparatus. The results suggest that the π,π☆ excited state is responsible for the reaction.

  通过使用通常的旋转木马设备估算固态的2,4,6-三异丙基二苯甲酮的光环化的量子产率。结果表明，π，π ☆激发态是反应的原因。
• Photocyclization reaction and triplet lifetime of hindered o-alkyl benzophenones
  作者：Yoshikatsu Ito、Yasutoshi Umehara、Yutaka Yamada、Teruo Matsuura

  DOI：10.1039/c39800001160

  日期：——

  The triplet lifetimes of hindered 4′-substituted-2,4,6-tri-isopropylbenzophenones decrease (increase) with the increasing electron-donating (withdrawing) ability of the ring substituents; this is the opposite effect to that expected from the rate of the intermolecular hydrogen-abstraction reaction of unhindered benzophenones.

  受阻的4'-取代的2,4,6-三异丙基二苯甲酮的三重态寿命随着环取代基的供电子（抽出）能力的增加而降低（增加）；这与不受阻碍的二苯甲酮的分子间吸氢反应速率所预期的相反。
• 4-[2,4,6-Tris(1-methylethyl)benzoyl]benzoic Acid (<i>S</i>)-(−)-Proline
  作者：T. Y. Fu、J. R. Scheffer、J. Trotter

  DOI：10.1107/s0108270197005295

  日期：1997.9.15

  The title compound, C23H28O3.C5H9NO2, is a 1:1 complex of the benzoic acid derivative and the (S)-proline zwitterion, with two formula units in the asymmetric unit (with pseudo-symmetry relationships between the separate components). The ketone carbonyl group in each benzoic acid molecule deviates slightly from a position normal to the plane of the triisopropylphenyl ring; the deviations (of about 16 degrees) are in opposite senses in the two molecules, so that the molecules have opposite conformational chiralities, leading to a nearly racemic photoproduct on solid-state photolysis.
• Diastereoselective Photocyclization of <i>N</i>-(<i>p</i>-(2,4,6-Triisopropylbenzoyl)benzoyl)-<scp>l</scp>- phenylalanine Methyl Ester in the Solid State
  作者：Yoshikatsu Ito、Gentaro Kano、Nobumasa Nakamura

  DOI：10.1021/jo980139g

  日期：1998.8.1
• Single-crystal-to-single-crystal photocyclization of 4-(2,4,6-triisopropylbenzoyl)benzoic acid in the salt crystal with (S)-phenylethylamine
  作者：Hideko Koshima、Yuya Ide、Michitaro Fukano、Kotaro Fujii、Hidehiro Uekusa

  DOI：10.1016/j.tetlet.2008.05.041

  日期：2008.7

  Ultraviolet irradiation of a salt crystal of 4-(2,4,6-triisopropylbenzoyl)benzoic acid with (S)-phenylethylamine promoted single-crystal-to-single-crystal photocyclization to give an enantiopure (R,R)-cyclopentenol and almost racemic cyclobutenol. The reaction paths were elucidated by X-ray crystallographic analysis of the crystal before and after irradiation. (C) 2008 Elsevier Ltd. All rights reserved.