α-cyclopropylbenzyl acetate | 7515-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-cyclopropylbenzyl acetate
• 英文别名: Phenyl-cyclopropyl-carbinol；Phenyl-cyclopropyl-carbinol-acetat；[Cyclopropyl(phenyl)methyl] acetate
• CAS: 7515-47-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: UTFHXGKNSLVKOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  α-cyclopropylbenzyl acetate 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 1-Phenyl--acetat
  参考文献：
  名称：

  Hanack,M. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 690, p. 98 - 114

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基环丙基甲酮 在 吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 α-cyclopropylbenzyl acetate
  参考文献：
  名称：

  Expanding substrate scope of lipase-catalyzed transesterification by the utilization of liquid carbon dioxide

  摘要：

  Secondary alcohols having bulky substituents on both sides of the chiral center are often poor substrates for most lipases. Here we reported that substrate scopes of two of the most used lipases, Candida antarctica lipase B and Burkholderia cepacia lipase, were found to be expanded toward more bulky secondary alcohols such as 1-phenyl-1-dodecanol and 2-methyl-1-phenyl-1-propanol by simply using them in liquid carbon dioxide as a solvent. The effects of solvents, reaction pressure, and pre-treatment of the enzyme with liquid CO2 on this acceleration phenomenon were also studied. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.052

文献信息

• Products from solvolysis reactions that form (2-phenylcyclopropyl)carbinyl cations
  作者：R. Esala P. Chandrasena、David Aebisher、Martin Newcomb

  DOI：10.1002/poc.951

  日期：2005.9

  Products from solvolytic reactions that form the (2-phenylcyclopropyl)carbinyl cation were determined. The majority of products (> 98%) derived from the 1-phenyl-3-butenyl cation, consistent with reports by Wiberg and co-workers. Small amounts of products derived from the 1-phenyl-1-cyclopropylmethyl cation also were found; these products were previously predicted to be formed from reactions of the

  确定了来自溶剂分解反应的形成（2-苯基环丙基）羰基阳离子的产物。大部分产品（> 98％）来自1-苯基-3-丁烯基阳离子，与Wiberg及其同事的报道一致。还发现了少量的衍生自1-苯基-1-环丙基甲基阳离子的产物。这些产物先前被预测是由标题阳离子的反应形成的。尽管1-苯基-1-环丙基甲基阳离子比1-苯基-3-丁烯基阳离子稳定得多，但是在各种溶剂分解条件下它不是动力学可及的。版权所有©2005 John Wiley＆Sons，Ltd.
• Cyclopropylcarbinyl compounds from homoallylic iodides
  作者：Lucio Previtera、Pietro Monaco、Lorenzo Mangoni

  DOI：10.1016/s0040-4039(01)80138-6

  日期：1984.1

  A simple synthesis of cyclopropylcarbinyl compounds based on the reaction of homoallylic iodides with silver salts in anhydrous medium is described.

  描述了基于均烯丙基碘化物与银盐在无水介质中反应的环丙基羰基化合物的简单合成方法。
• Diverse Alkyl–Silyl Cross-Coupling via Homolysis of Unactivated C(sp³)–O Bonds with the Cooperation of Gold Nanoparticles and Amphoteric Zirconium Oxides
  作者：Hiroki Miura、Masafumi Doi、Yuki Yasui、Yosuke Masaki、Hidenori Nishio、Tetsuya Shishido

  DOI：10.1021/jacs.2c12311

  日期：2023.3.1

  the degradation of polyesters and the synthesis of organosilanes were realized concurrently by the unique catalysis of supported gold nanoparticles. Mechanistic studies corroborated the notion that the generation of alkyl radicals is involved in C(sp3)–Si coupling and the cooperation of gold and an acid–base pair on ZrO2 is responsible for the homolysis of stable C(sp3)–O bonds. The high reusability and

  由于C(sp 3 )–O键是天然和人工有机分子中普遍存在的化学基序，因此C(sp 3 )–O键的普遍转化将成为实现碳中和的关键技术。我们在此报告负载在两性金属氧化物（即 ZrO 2 ）上的金纳米粒子通过未活化的 C(sp 3 )–O 键均裂有效地产生烷基自由基，从而促进 C(sp 3)–Si键的形成可得到多种有机硅化合物。多种酯类和醚类（市售的或容易从醇合成的）参与乙硅烷进行的多相金催化甲硅烷基化反应，以高产率生成各种烷基、烯丙基、苄基和丙二烯基硅烷。此外，这种用于C(sp 3 )–O键转化的新型反应技术可应用于聚酯的升级回收，即通过负载金纳米粒子的独特催化作用同时实现聚酯的降解和有机硅烷的合成。机理研究证实了烷基自由基的产生与 C(sp 3 )–Si 偶联以及金和酸碱对在 ZrO 2上的合作有关的观点负责稳定 C(sp 3 )–O 键的均裂。多相金催化剂的高可重用性和空气耐受性以及简单、
• Deoxygenative Silylation of C(sp³)–O Bonds with Hydrosilane by Cooperative Catalysis of Gold Nanoparticles and Solid Acids
  作者：Hiroki Miura、Yuki Yasui、Yosuke Masaki、Masafumi Doi、Tetsuya Shishido

  DOI：10.1021/acscatal.3c00973

  日期：2023.5.19

  Efficient deoxygenative silylation of C(sp3)–O bonds with hydrosilanes by supported Au catalysts is described. Gold nanoparticles supported on TiO2 enabled various hydrosilanes to be used as sources of silyl groups in C–Si cross-coupling reactions. A variety of alkyl acetates and propargyl carbonates participated in the Au-catalyzed reactions to furnish the corresponding alkyl and allenylsilanes in

  描述了负载型 Au 催化剂对 C(sp 3 )–O 键与氢硅烷的有效脱氧硅烷化。负载在 TiO 2上的金纳米粒子使各种氢硅烷能够在 C-Si 交叉偶联反应中用作甲硅烷基的来源。各种乙酸烷基酯和碳酸炔丙酯参与了金催化的反应，以高产率提供相应的烷基和烯丙基硅烷。此外，Au/TiO 2对环醚的开环甲硅烷基化也有效。详细的机理研究证实标题反应涉及甲硅烷基和烷基自由基中间体的形成，而 Au 纳米颗粒作为单电子转移催化剂与金属氧化物表面的路易斯酸位点的合作是氢硅烷异常反应性的原因特定的 C(sp 3 )–Si 键形成。
• 10.1021/acscatal.4c03396
  作者：Xu, Chen-Wei、Yan, Si-Yi、Xu, Hui、Wang, Sai、Gu, Li-Qun、Xu, Pei、Yin, Long、Zhu, Xu

  DOI：10.1021/acscatal.4c03396

  日期：——

  Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source and reductant as well as the promoter is described. Neither a pre-established CO2 atmosphere nor external electron donors are required as the TBAO is crucial for the transformation. Various primary, secondary, and tertiary

  本文描述了一种光氧化还原中性策略，以草酸四丁基铵 (TBAO) 作为羰基源和还原剂以及促进剂，通过 C(sp 3 )-O 键活化和裂解来羧化酰化醇。既不需要预先建立的CO 2气氛，也不需要外部电子供体，因为TBAO对于转变至关重要。各种伯醇、仲醇和叔醇可以顺利转化为相应的芳基乙酸，这是多种药物的核心结构。