(9H-芴-9-基)甲基 烯丙基氨基甲酸酯 | 856438-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (9H-芴-9-基)甲基 烯丙基氨基甲酸酯
• 中文别名: (9H-芴-9-基)甲基烯丙基氨基甲酸酯；9H-芴-9-基甲基N-(丙-2-烯-1-基)氨基甲酸酯
• 英文名称: (9H-fluoren-9-yl)methyl allylcarbamate
• 英文别名: N-Fmoc-allylamine；9H-fluoren-9-ylmethyl N-(prop-2-en-1-yl)carbamate；9H-fluoren-9-ylmethyl N-prop-2-enylcarbamate
• CAS: 856438-23-8
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: DUTZXTJPEKETHY-UHFFFAOYSA-N

物化性质

• 沸点：
  454.4±24.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (9H-芴-9-基)甲基 烯丙基氨基甲酸酯 在 间氯过氧苯甲酸 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以76%的产率得到2,3-epoxy-N-(9-fluorenylmethoxycarbonyl)propylamine
  参考文献：
  名称：

  Stable attachment of the HMB-linker to continuous cellulose membranes for parallel solid phase spot synthesis

  摘要：

  Peptides and other oligomeric molecules were prepared on continuous cellulose membranes using a stably attached p-hydroxymethyl-benzoic acid (HMB)(1) linker. After attachment of N-protected 1,2-epoxy-propylamine to the support via an ether bond, the HMB linker was coupled to this construct resulting in a orthogonal safety-catch linkage suitable for solid phase synthesis. As an application, several peptides, peptoids and carbohydrate-peptide conjugates were prepared and analyzed by HPLC and mass spectrometry. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02508-7
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 丙烯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以72%的产率得到(9H-芴-9-基)甲基 烯丙基氨基甲酸酯
  参考文献：
  名称：

  Stable attachment of the HMB-linker to continuous cellulose membranes for parallel solid phase spot synthesis

  摘要：

  Peptides and other oligomeric molecules were prepared on continuous cellulose membranes using a stably attached p-hydroxymethyl-benzoic acid (HMB)(1) linker. After attachment of N-protected 1,2-epoxy-propylamine to the support via an ether bond, the HMB linker was coupled to this construct resulting in a orthogonal safety-catch linkage suitable for solid phase synthesis. As an application, several peptides, peptoids and carbohydrate-peptide conjugates were prepared and analyzed by HPLC and mass spectrometry. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02508-7

文献信息

• Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase
  作者：Yuichi Masuda、Chitose Maruyama、Kyuichi Kawabata、Yoshimitsu Hamano、Takayuki Doi

  DOI：10.1016/j.tet.2016.07.050

  日期：2016.9

  A synthesis of (2S,3R,4R)-3,4-dihydroxyarginine, a metabolic intermediate of streptothricin, was accomplished. The (3R,4R)-dihydroxy groups were constructed by asymmetric syn-dihydroxylation of (E)-alkene, which was obtained by cross-metathesis of allylamine and l-vinylglycine derivatives. The synthesis of (2S,3S,4S)-3,4-dihydroxyarginine was also achieved in the same manner. The (2S,3R,4R)-3,4-dihydroxyarginine

  完成了链霉菌素的代谢中间体（2 S，3 R，4 R）-3,4-二羟基精氨酸的合成。通过烯丙基胺和1-乙烯基甘氨酸衍生物的交叉复分解获得的（E）-烯烃的不对称顺-二羟基化反应来构建（3 R，4 R）-二羟基基团。（2 S，3 S，4 S）-3,4-二羟基精氨酸的合成也以相同的方式完成。（2 S，3 R，4 R）-3,4-二羟基精氨酸与（2 S，3 S，4 S）-3,4-二羟基精氨酸不同，对诱导型一氧化氮合酶具有抑制活性。
• Hydrochlorofluoromethylation of unactivated alkenes with chlorofluoroacetic acid
  作者：Claudio F. Meyer、Sandrine M. Hell、Jeroen B.I. Sap、Antonio Misale、Aldo Peschiulli、Daniel Oehlrich、Andrés A. Trabanco、Véronique Gouverneur

  DOI：10.1016/j.tet.2019.130679

  日期：2019.11

  An operationally simple method enabling hydrochlorofluoromethylation of unactivated alkenes under visible light activation is reported. The procedure has various benefits. It uses commercially available and inexpensive chlorofluoroacetic acid and phenyliodine(III) diacetate for the generation of the required chlorofluoromethyl radical, it converts feedstock olefins into attractive 1-chloro-1-fluoroalkanes

  据报道，一种操作简单的方法能够在可见光活化下使未活化的烯烃进行氢氯氟甲基化。该程序具有多种好处。它使用可商购和廉价的氯氟乙酸和二乙酸苯碘（III）生成所需的氯氟甲基基团，将原料烯烃转化为有吸引力的1-氯-1-氟烷烃，并且可以耐受多种官能团。氯氟甲基具有与亲核二氟甲基相似的对烯烃的反应性。
• N-Urethane protection of amines and amino acids in an ionic liquid
  作者：M. L. Di Gioia、A. Gagliardi、A. Leggio、V. Leotta、E. Romio、A. Liguori

  DOI：10.1039/c5ra12121c

  日期：——

  Fmoc and Cbz direct protection of amino groups is efficiently performed in [Bmim][BF₄] ionic liquid.

  Fmoc和Cbz对氨基团的直接保护在[Bmim][BF₄]离子液体中高效进行。
• Hydrodifluoromethylation of Alkenes with Difluoroacetic Acid
  作者：Claudio F. Meyer、Sandrine M. Hell、Antonio Misale、Andrés A. Trabanco、Véronique Gouverneur

  DOI：10.1002/anie.201903801

  日期：2019.6.24

  hydrodifluoromethylation of alkenes is reported using difluoroacetic acid and phenyliodine(III) diacetate in tetrahydrofuran under visible‐light activation. This metal‐free approach stands out as it uses inexpensive reagents, does not require a photocatalyst, and displays broad functional group tolerance. The procedure is also operationally simple and scalable, and provides access in one step to high‐value

  据报道，在可见光下，在四氢呋喃中使用二氟乙酸和二乙酸苯碘（III），是一种用于烯烃的区域选择性氢二氟甲基化的简便方法。这种无金属方法因其使用廉价的试剂，不需要光催化剂且具有宽泛的官能团耐受性而脱颖而出。该程序在操作上也很简单且可扩展，并且一步一步即可提供用于药物化学的高价值构建基块。
• Nickel-Catalyzed Synthesis of Enamides and Enecarbamates<i>via</i>Isomerization of Allylamides and Allylcarbamates
  作者：Juliette Halli、Philipp Kramer、Maren Bechthold、Georg Manolikakes

  DOI：10.1002/adsc.201500461

  日期：2015.10.12

  A single-component, air-stable nickel precatalyst can catalyze the isomerization of allylamides for the synthesis of enamides. The scope of the reaction encompasses various substituted allylamides and allylcarbamates as well as homoallylamides. The reaction can be performed on a multigram-scale without specialized glove-box equipment or Schlenk techniques.

  单组分，空气稳定的镍预催化剂可催化烯丙基酰胺的异构化反应，以合成烯酰胺。反应范围包括各种取代的烯丙基酰胺和烯丙基氨基甲酸酯以及均烯丙基。该反应无需专门的手套箱设备或Schlenk技术即可在数克范围内进行。