1-bromomethyl-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene | 444682-61-5

• 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: 1-bromomethyl-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene
• 英文别名: 1-(4,4,5,5,6,6,7,7,7-Nonafluoroheptyloxy)-4-(bromomethyl)benzene；1-(bromomethyl)-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptoxy)benzene
• CAS: 444682-61-5
• 化学式: C₁₄H₁₂BrF₉O
• 分子量: 447.138
• InChiKey: BITYAENWAIVASR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-bromomethyl-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 12.5h， 生成 1-((2-iodoethoxy)methyl)-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679
• 作为产物：
  描述：

  4-(1H,1H,2H,2H,3H,3H-全氟庚氧基)苄醇 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-bromomethyl-4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzene
  参考文献：
  名称：

  Murisolins 的 28 成员立体异构体库的全合成

  摘要：

  报道了两个 16 人库的 murisolin 异构体的总合成。在第一个库中，含氟 PMB（对甲氧基苄基）基团编码构型，通过 Shi 环氧化和（可选）Mitsunobu 反应制备四种二羟基四氢呋喃的四种混合物。混合物通过 Kocienski-Julia 反应与单一羟基丁烯内酯偶联，然后氢化。分层和去标签提供 16 种纯立体异构体。在第二个合成中，四种含氟标记的二羟基四氢呋喃的单一混合物与带有 DMB（二甲氧基苄基）基团衍生物的羟基丁烯内酯的四化合物混合物偶联，其中低聚乙二醇 (OEG) 单元编码 C4 和 C34 的构型. 16-化合物混合物进行氢化、双重分层、并去标签以提供 16 种异构纯的 murisolins。这些异构体中有 12 个是新的，而第一个库中的四个匹配样品。

  DOI：

  10.1021/ja061801q

文献信息

• Simultaneous Preparation of Four Truncated Analogues of Discodermolide by Fluorous Mixture Synthesis
  作者：Dennis P. Curran、Takashi Furukawa

  DOI：10.1021/ol026084t

  日期：2002.6.1

  [structure: see text] Four truncated analogues of the natural product discodermolide were synthesized in a single synthetic sequence. Precursors bearing four different groups at C22, each with a unique fluorous p-methoxybenzyl substituent on the C17 hydroxy group, were mixed and taken through an nine-step sequence. Demixing by fluorous chromatography followed by deprotection and purification provided

  [结构：见正文]天然产物discodermolide的四个截短的类似物以单个合成序列合成。混合在C22上带有四个不同基团的前体，每个基团在C17羟基上具有一个独特的氟对甲氧基苄基取代基，并经过九步操作。通过荧光色谱法分离，然后脱保护和纯化，以3-7％的总产率提供了各个类似物，并节省了24个合成步骤。推荐使用氟混合物合成作为一种新技术，在一次多步合成中制备多个天然产物类似物。
• Total Synthesis of a 28-Member Stereoisomer Library of Murisolins
  作者：Dennis P. Curran、Qisheng Zhang、Cyrille Richard、Hejun Lu、Venugopal Gudipati、Craig S. Wilcox

  DOI：10.1021/ja061801q

  日期：2006.7.1

  library, fluorous PMB (p-methoxybenzyl) groups encode configurations, and four mixtures of four dihydroxy-tetrahydrofurans are prepared by Shi epoxidation followed (optionally) by Mitsunobu reaction. The mixtures are coupled by Kocienski-Julia reaction with a single hydroxybutenolide followed by hydrogenation. Demixing and detagging provide the 16 pure stereoisomers. In the second synthesis, a single

  报道了两个 16 人库的 murisolin 异构体的总合成。在第一个库中，含氟 PMB（对甲氧基苄基）基团编码构型，通过 Shi 环氧化和（可选）Mitsunobu 反应制备四种二羟基四氢呋喃的四种混合物。混合物通过 Kocienski-Julia 反应与单一羟基丁烯内酯偶联，然后氢化。分层和去标签提供 16 种纯立体异构体。在第二个合成中，四种含氟标记的二羟基四氢呋喃的单一混合物与带有 DMB（二甲氧基苄基）基团衍生物的羟基丁烯内酯的四化合物混合物偶联，其中低聚乙二醇 (OEG) 单元编码 C4 和 C34 的构型. 16-化合物混合物进行氢化、双重分层、并去标签以提供 16 种异构纯的 murisolins。这些异构体中有 12 个是新的，而第一个库中的四个匹配样品。
• Fluorous Mixture Synthesis of Stereoisomer Libraries:  Total Syntheses of (+)-Murisolin and Fifteen Diastereoisomers
  作者：Qisheng Zhang、Hejun Lu、Cyrille Richard、Dennis P. Curran

  DOI：10.1021/ja038542e

  日期：2004.1.1

  The synthesis of a stereoisomer library of 16 murisolins in individual pure form by fluorous mixture synthesis is reported. Four stereoisomeric precursors are tagged with different fluorous tags, and the resulting mixture is taken through the synthesis with four splits and late stage demixing and detagging to give all 16 products. These products exhibit only six different sets of NMR spectra, but all

  报道了通过含氟混合物合成合成单个纯形式的 16 种 murisolins 立体异构体库。四种立体异构前体用不同的氟标签进行标记，所得混合物通过四次拆分和后期分层和去标签的合成得到所有 16 种产品。这些产品仅显示六组不同的 NMR 光谱，但都可以通过手性 HPLC 进行区分。murisolin 的结构已确认，但 murisolin A 和 16,19-cis-murisolin 的结构可能永远无法确定，因为在天然样品上收集的数据不足以将它们与其他异构体区分开来。
• Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters
  作者：Reena Bajpai、Dennis P. Curran

  DOI：10.1021/ja2082679

  日期：2011.12.21

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.