[2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate | 1182723-38-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: [2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS: 1182723-38-1
• 化学式: C₂₉H₂₁F₁₄NO₅
• 分子量: 729.467
• InChiKey: AHRFRJKEEGTHMH-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  558.9±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 [2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate 在 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以98%的产率得到f₃-Fmoc-Ala-OH
  参考文献：
  名称：

  氟-Fmoc保护策略的三肽和五肽的氟混合物合成

  摘要：

  摘要 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。

  DOI：

  10.1055/s-0036-1588698
• 作为产物：
  描述：

  2,7-二硝基芴 在 sodium tetrahydroborate 、 tetrafluoroboric acid 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 N,N-二甲基苯胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 68.5h， 生成 [2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate
  参考文献：
  名称：

  Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents

  摘要：

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.083

文献信息

• Liquid-Phase Split-Type Combinatorial Synthesis of Tripeptide Derivatives Encoded by Fluorous Fmoc Reagents
  作者：Masato Matsugi、Yuya Sugiyama、Masaki Hirose、Junko Matsui、Natsuki Endo、Hiromi Hamamoto、Takayuki Shioiri

  DOI：10.1055/s-0033-1339924

  日期：——

  A liquid-phase mixture synthesis of 18 tripeptides, some of which are analogues of ACE inhibitors, was effectively conducted by using fluorous Fmoc reagents as encoding tags.
• Fluorous Mixture Synthesis of Tripeptides and Pentapeptides Using­ a Fluorous-Fmoc Protection Strategy
  作者：Masato Matsugi、Yuya Sugiyama、Ryuhei Shirai、Masaki Hirose、Tomoko Watanabe、Ayana Yoshida、Natsuki Endo、Toshiya Hayashi、Takayuki Shioiri

  DOI：10.1055/s-0036-1588698

  日期：——

  split-type synthesis of various tripeptides and pentapeptides was conducted using a fluorous-Fmoc protection strategy. Fluorous-Fmoc reagents were effectively used as both the protecting group for the amino function and the encoding tag for the amino acid structure. Several of the synthetic peptides prepared showed high activities in an ACE inhibitory assay. A liquid-phase split-type synthesis of various

  摘要 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。 使用氟-Fmoc保护策略进行了各种三肽和五肽的液相分裂型合成。氟-Fmoc试剂可有效地用作氨基功能的保护基和氨基酸结构的编码标签。所制备的几种合成肽在ACE抑制试验中显示出高活性。
• Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents
  作者：Yuya Sugiyama、Natsuki Endo、Kazuki Ishihara、Yuki Kobayashi、Hiromi Hamamoto、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tet.2015.05.083

  日期：2015.7

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.