N-(9-fluorenylmethoxycarbonyl)dicyclohexylamine | 309972-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)dicyclohexylamine
• 英文别名: 9-fluorenylmethyl N,N-dicyclohexylcarbamate；Carbamic acid, dicyclohexyl-, 9H-fluoren-9-ylmethyl ester；9H-fluoren-9-ylmethyl N,N-dicyclohexylcarbamate
• CAS: 309972-30-3
• 化学式: C₂₇H₃₃NO₂
• 分子量: 403.565
• InChiKey: DKSDZDDVEOVSKP-UHFFFAOYSA-N

物化性质

• 沸点：
  551.8±20.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 二环己胺 以 乙醚 为溶剂， 以77.9%的产率得到N-(9-fluorenylmethoxycarbonyl)dicyclohexylamine
  参考文献：
  名称：

  Nonlinear organic reaction of 9-fluorenylmethyl carbamates as base amplifiers to proliferate aliphatic amines and their application to a novel photopolymer system

  摘要：

  描述了一种新颖的基本增殖概念，以提高对基础敏感材料的光敏性，展示了9-芴乙基氨基甲酸酯向脂肪胺的自催化转化。作为基础放大器的9-芴乙基氨基甲酸酯经历了一种基础催化的断裂反应，从而释放出相应的胺，该胺可以作为催化剂分解母体分子，进而导致自催化分解。因此，从等摩尔量的氨基甲酸酯中生成胺，并利用相同胺的催化量。1-(9-芴乙氧基羧基)-哌啶和1-(9-芴乙氧基羧基)环己胺由于在中性条件下的热稳定性和高基础催化活性而适合作为基础放大器。根据结果，设计了1,3-双[1-(9-芴乙氧基羧基)-4-哌啶基]丙烷和1,6-双[(9-芴乙氧基)羧基氨基]己烷作为基础放大器，在光铵生成剂存在的情况下，释放脂肪二胺以交联聚（甘油甲基丙烯酸酯）进行光化学反应。添加基础放大器使聚合物的光敏性特性分别提高了16和50倍。

  DOI：

  10.1039/b311358b

文献信息

• Photochemical Protection of Amines with Cbz and Fmoc Groups
  作者：Céline Helgen、Christian G. Bochet

  DOI：10.1021/jo026581n

  日期：2003.3.1

  The photochemical conversion of amines into carbamates was achieved using N-Cbz- N-Fmoc-, and N-Boc-5,7-dinitroindolines. This reaction allows the protection of amines in neutral medium. Primary and unhindered secondary amines were protected to yield their benzyloxycarbonyl- and 9-fluorenylmethoxycarbonyl derivatives efficiently, whereas bulky amines or anilines gave low yields or no product. On the other hand, the formation of N-Boc compounds, although possible, proceeded only with low yields.
• DECOMPOSABLE RESIN COMPOSITION AND PATTERN-FORMING MATERIAL INCLUDING THE SAME
  申请人：Taguchi Yoshinori

  公开号：US20080070154A1

  公开（公告）日：2008-03-20

  A decomposable resin composition contains a base generator, and a polyurethane resin capable of being decomposed with a base generated from the base generator.
• US7718343B2
  申请人：——

  公开号：US7718343B2

  公开（公告）日：2010-05-18
• Nonlinear organic reaction of 9-fluorenylmethyl carbamates as base amplifiers to proliferate aliphatic amines and their application to a novel photopolymer system
  作者：Koji Arimitsu、Kunihiro Ichimura

  DOI：10.1039/b311358b

  日期：——

  A novel concept of base proliferation for improving the photosensitivity of base-sensitive materials is described by presenting the autocatalytic transformation of 9-fluorenylmethyl carbamates to aliphatic amines. A 9-fluorenylmethyl carbamate, as a base amplifier, was subjected to a base-catalysed fragmentation reaction to liberate the corresponding amine, which can then act as a catalyst for decomposing parent molecules, leading to autocatalytic decomposition. Consequently, the amine is generated from an equimolar amount of the carbamate using a catalytic amount of the same amine. 1-(9-Fluorenylmethoxycarbonyl)piperidine and 1-(9-fluorenylmethoxycarbonyl)cyclohexylamine were suitable as base amplifiers because of their thermal stability under neutral conditions and high base-catalytic reactivity. On the basis of the results, 1,3-bis[1-(9-fluorenylmethoxycarbonyl)-4-piperidyl]propane and 1,6-bis[(9-fluorenylmethoxy)carbonylamino]hexane were designed as base amplifiers which liberate aliphatic diamines to crosslink poly(glycidyl methacrylate) photochemically in the presence of a photobase generator. Addition of the base amplifiers resulted in a marked improvement of the photosensitivity characteristics of the polymer by a factor of 16 and 50, respectively.

  描述了一种新颖的基本增殖概念，以提高对基础敏感材料的光敏性，展示了9-芴乙基氨基甲酸酯向脂肪胺的自催化转化。作为基础放大器的9-芴乙基氨基甲酸酯经历了一种基础催化的断裂反应，从而释放出相应的胺，该胺可以作为催化剂分解母体分子，进而导致自催化分解。因此，从等摩尔量的氨基甲酸酯中生成胺，并利用相同胺的催化量。1-(9-芴乙氧基羧基)-哌啶和1-(9-芴乙氧基羧基)环己胺由于在中性条件下的热稳定性和高基础催化活性而适合作为基础放大器。根据结果，设计了1,3-双[1-(9-芴乙氧基羧基)-4-哌啶基]丙烷和1,6-双[(9-芴乙氧基)羧基氨基]己烷作为基础放大器，在光铵生成剂存在的情况下，释放脂肪二胺以交联聚（甘油甲基丙烯酸酯）进行光化学反应。添加基础放大器使聚合物的光敏性特性分别提高了16和50倍。