1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)hydrazine dicarboxylate | 452912-12-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)hydrazine dicarboxylate
• 英文别名: 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl N-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctoxycarbonylamino)carbamate
• CAS: 452912-12-8
• 化学式: C₁₈H₁₀F₂₆N₂O₄
• 分子量: 812.247
• InChiKey: LQTGIHYIGPXSQR-UHFFFAOYSA-N

物化性质

• 沸点：
  384.9±42.0 °C(Predicted)
• 密度：
  1.649±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)hydrazine dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 吡啶 为溶剂， 以79%的产率得到bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)diazo dicarboxylate
  参考文献：
  名称：

  氟偶氮二羧酸酯的合成：迈向更清洁的Mitsunobu反应

  摘要：

  描述了偶氮二羧酸二乙酯（DEAD）的氟类似物的合成，并给出了其在Mitsunobu反应中使用的初步结果。荧光提取方法的使用表明色谱对于反应纯化不是必需的。

  DOI：

  10.1016/s0040-4039(02)00322-2
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl chloroformate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以80%的产率得到1,2-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)hydrazine dicarboxylate
  参考文献：
  名称：

  氟偶氮二羧酸酯的合成：迈向更清洁的Mitsunobu反应

  摘要：

  描述了偶氮二羧酸二乙酯（DEAD）的氟类似物的合成，并给出了其在Mitsunobu反应中使用的初步结果。荧光提取方法的使用表明色谱对于反应纯化不是必需的。

  DOI：

  10.1016/s0040-4039(02)00322-2

文献信息

• A recyclable fluorous hydrazine-1,2-bis(carbothioate) with NCS as efficient catalysts for acetalization of aldehydes
  作者：Yi-Wei Zhu、Wen-Bin Yi、Chun Cai

  DOI：10.1039/c3nj41182f

  日期：——

  A fluorous hydrazine-carbothioate organocatalyst was prepared. Together with NCS, the catalyst showed a good activity in acetalization of aldehydes and alcohols. It could be recovered from the reaction mixture by fluorous solid-phase extraction (F-SPE) with excellent purity for direct reuse.

  制备了氟肼基-硫代碳酸盐有机催化剂。与NCS一起，该催化剂在醛和醇的缩醛化中显示出良好的活性。可以通过氟固相萃取（F-SPE）从反应混合物中回收具有优良纯度的氟，以便直接重复使用。
• Fluorous Mitsunobu reagents and reactions
  作者：Sivaraman Dandapani、Dennis P. Curran

  DOI：10.1016/s0040-4020(02)00205-3

  日期：2002.5

  A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H4)2PPh] and new [C8F17CH2CH2C6H4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)NNCOOCH2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction

  引入了完全氟的Mitsunobu反应程序。它既使用现有的[（C 6 F 13 CH 2 CH 2 C 6 H 4）2 PPh]，又使用新的[C 8 F 17 CH 2 CH 2 C 6 H 4 PPh 2 ]氟膦和新的氟偶氮二羧酸酯（C 6 ˚F 13 CH 2 CH 2 OC（O）NNCOOCH 2 CH 2 C ^ 6 ˚F 13）。该过程涉及在典型的Mitsunobu条件下在THF中与代表性的亲核试剂和醇进行平行反应，然后在氟硅石上进行快速固相萃取（spe），从而提供了具有优良收率的清洁产品。可以容易地分离出包含氧化的氧化膦和还原的酰肼的氟级分，并且可以通过适当的氧化还原反应以高收率再生起始试剂，以供再利用。
• Highly efficient synthesis of polysubstituted 1,2-dihydroquinolines via tandem reaction of α-ketoesters and arylamines catalyzed by fluorous hydrazine-1,2-bis(carbothioate) and NCS
  作者：Yi-Wei Zhu、Jin-Long Qian、Wen-Bin Yi、Chun Cai

  DOI：10.1016/j.tetlet.2012.11.143

  日期：2013.2

  A simple and convenient tandem reaction of alpha-ketoesters with primary or secondary aromatic amines for the synthesis of polysubstituted 1,2-dihydroquinolines has been developed. The catalytic system (fluorous hydrazine-1,2-bis(carbothioate)/NCS) of the reaction has the advantages of operational simplicity, high efficiency, as well as easy recyclability. (c) 2012 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of α-Chloroketones Catalyzed by Fluorous Hydrazine-1,2-Bis(Carbothioate) Organocatalyst
  作者：Yi-Wei Zhu、Yi-Xin Shi

  DOI：10.1007/s10562-015-1676-3

  日期：2016.3

  A novel and recoverable fluorous hydrazine-carbothioate organocatalyst was prepared. It could catalyze alpha-chlorination of alkyl ketones with N-chlorosuccinimide as chlorine source under mild reaction conditions. The reaction afforded the corresponding alpha-chlorinated carbonyl compounds with excellent yields at rapid reaction speed.
• Synthesis of fluorous azodicarboxylates: towards cleaner Mitsunobu reactions
  作者：Adrian P Dobbs、Caroline McGregor-Johnson

  DOI：10.1016/s0040-4039(02)00322-2

  日期：2002.4

  The synthesis of a fluorous analogue of diethyl azodicarboxylate (DEAD) is described and preliminary results for its use in the Mitsunobu reaction given. Use of fluorous extraction methods have shown that chromatography is not necessary for reaction purification.

  描述了偶氮二羧酸二乙酯（DEAD）的氟类似物的合成，并给出了其在Mitsunobu反应中使用的初步结果。荧光提取方法的使用表明色谱对于反应纯化不是必需的。