1-Phenyl-1-(3-(methoxycarbonyl)propyl)diazomethane | 160848-23-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-Phenyl-1-(3-(methoxycarbonyl)propyl)diazomethane
• 英文别名: methyl (5Z)-5-diazo-5-phenylpentanoate
• CAS: 160848-23-7
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: BKTCQKRBVBVDHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  足球烯 、 1-Phenyl-1-(3-(methoxycarbonyl)propyl)diazomethane 25.0~55.0 ℃ 、137.9 kPa 条件下， 反应 0.04h， 以37%的产率得到PCBM
  参考文献：
  名称：

  使用带有钠灯的流动光反应器可扩展地合成[6,6]-苯基-C61-丁酸甲基酯（PCBM）

  摘要：

  通过使用带有Na灯的流动光反应器，富勒烯向[6,6]-苯基-C 61-丁酸甲酯（PCBM）的光异构化非常有效地进行。结果，通过连续流合成（0.79 g / 3.3 h）实现了可扩展的PCBM合成。

  DOI：

  10.1002/ejoc.201700745
• 作为产物：
  描述：

  methyl 4-benzoylbutyrate p-tosylhydrazone 在 吡啶 、 sodium methylate 作用下， 生成 1-Phenyl-1-(3-(methoxycarbonyl)propyl)diazomethane
  参考文献：
  名称：

  PCBM 甲烷富勒烯（C60 和 C70）的高效微波辅助合成

  摘要：

  PCBM是一种富勒烯衍生物（苯基-C61-丁酸甲酯），被认为是最好的n型有机半导体之一，在有机光伏太阳能电池中发挥着相关作用。许多努力致力于优化 PCBM 衍生物的合成。在本文中，PC61BM 和 PC71BM 富勒烯单加合物以及 PCBM 类衍生物在微波辐射下通过一步环丙烷化反应成功制备。在短时间内以良好的收率收集产物，在此期间，开放的 [5,6] 异构化为封闭的 [6,6] 形式在原位发生。此外，通过使用两个辐射循环，还以良好的产率获得了一系列双加合物类 PCBM 衍生物的混合物。

  DOI：

  10.1002/ejoc.201403563

文献信息

• Efficient Microwave-Assisted Synthesis of PCBM Methanofullerenes (C₆₀and C₇₀)
  作者：Caroline Hadad、Zois Syrgiannis、Aurelio Bonasera、Maurizio Prato

  DOI：10.1002/ejoc.201403563

  日期：2015.3

  devoted to the optimization of the synthesis of PCBM derivatives. In this paper, PC61BM and PC71BM fullerene mono-adducts but also PCBM-like derivatives are successfully prepared by a one-step cyclopropanation reaction under microwave irradiation. The products are collected in good yields in short time, during which isomerization of the open [5,6] to the closed [6,6] form takes place in situ. In addition

  PCBM是一种富勒烯衍生物（苯基-C61-丁酸甲酯），被认为是最好的n型有机半导体之一，在有机光伏太阳能电池中发挥着相关作用。许多努力致力于优化 PCBM 衍生物的合成。在本文中，PC61BM 和 PC71BM 富勒烯单加合物以及 PCBM 类衍生物在微波辐射下通过一步环丙烷化反应成功制备。在短时间内以良好的收率收集产物，在此期间，开放的 [5,6] 异构化为封闭的 [6,6] 形式在原位发生。此外，通过使用两个辐射循环，还以良好的产率获得了一系列双加合物类 PCBM 衍生物的混合物。
• Solvation-Free Li⁺ Lewis Acid Enhancing Reaction: Kinetic Study of [5,6]-Li⁺@PCBM to [6,6]-Li⁺@PCBM
  作者：Yue Ma、Hiroshi Ueno、Hiroshi Okada、Sergei Manzhos、Yutaka Matsuo

  DOI：10.1021/acs.orglett.0c02570

  日期：2020.9.18

  Kinetic parameters for the [5,6]- to [6,6]-[Li+@PCBM]TFSI– transformation were determined experimentally, revealing a ca. 700-fold faster reaction rate at 423 K than empty PCBM and a 57.4 kJ mol–1 lower activation energy. The encapsulated Li+ can be considered as solvation-free Li+, forming a 1:1 complex with the substrate.

  通过实验确定了[5,6]-到[6,6]-[Li + @PCBM] TFSI –转化的动力学参数。在423 K下，反应速率比空PCBM快700倍，活化能低57.4 kJ mol –1。封装的Li +可以认为是无溶剂化的Li +，与底物形成1：1的络合物。
• Higher fullerenes useful as radical scavengers
  申请人：Kronholm F. David

  公开号：US20050239717A1

  公开（公告）日：2005-10-27

  Chemically functionalized fullerenes are useful in various applications as radical scavengers. These chemically functionalized fullerenes offer the advantages of preservation of the high innate radical scavenging efficiency of the fullerene cage and ease of synthesis of fullerene derivatives of desirably altered chemical and physical properties and single isomers. Further, they are based on a common intermediate chemistry and intermediates can be easily functionalized and tailored to various requirements.

  化学功能化富勒烯可作为自由基清除剂用于各种用途。这些化学官能化富勒烯具有以下优点：保留了富勒烯笼固有的高自由基清除效率，易于合成化学和物理性质发生理想改变的富勒烯衍生物和单一异构体。此外，它们基于通用的中间体化学，中间体可以很容易地进行官能化和定制，以满足各种要求。
• High-efficiency fullerene-based radical scavengers
  申请人：Kronholm F. David

  公开号：US20050245606A1

  公开（公告）日：2005-11-03

  Chemically functionalized fullerenes are useful in various applications as radical scavengers. These chemically functionalized fullerenes offer the advantages of preservation of the high innate radical scavenging efficiency of the fullerene cage and ease of synthesis of fullerene derivatives of desirably altered chemical and physical properties and single isomers. Further, they are based on a common intermediate chemistry and intermediates can be easily functionalized and tailored to various requirements.

  化学功能化富勒烯可作为自由基清除剂用于各种用途。这些化学官能化富勒烯具有以下优点：保留了富勒烯笼固有的高自由基清除效率，易于合成化学和物理性质发生理想改变的富勒烯衍生物和单一异构体。此外，它们基于通用的中间体化学，中间体可以很容易地进行官能化和定制，以满足各种要求。
• Preparation and Characterization of Fulleroid and Methanofullerene Derivatives
  作者：Jan C. Hummelen、Brian W. Knight、F. LePeq、Fred Wudl、Jie Yao、Charles L. Wilkins

  DOI：10.1021/jo00108a012

  日期：1995.2

  We describe the synthesis and complete characterization of soluble derivatives of C-60 for applications to physics and biology. The goal of the strategy was to have a ''modular'' approach in order to be able to easily vary a functional group attached indirectly to the cluster. The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy). The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes. An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques. This problem was solved by the use of MALDIMS. The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives. Both isomeric forms ([5,6], fulleroid and [6,6], methanofullerene) of the C-61 clusters were prepared. The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively. The fulleroid and methano-fullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.