2-oxohexyl-phosphonic acid bis(2,2,2-trifluoroethyl)ester | 1196668-34-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-oxohexyl-phosphonic acid bis(2,2,2-trifluoroethyl)ester
• 英文别名: bis(2,2,2-trifluoroethyl) (2-oxohexyl)phosphonate；(2-Oxohexyl)phosphonic acid bis(2,2,2-trifluoroethyl) ester；1-[bis(2,2,2-trifluoroethoxy)phosphoryl]hexan-2-one
• CAS: 1196668-34-4
• 化学式: C₁₀H₁₅F₆O₄P
• 分子量: 344.191
• InChiKey: BWBJDHHEAWMNGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-oxohexyl-phosphonic acid bis(2,2,2-trifluoroethyl)ester 、 苯甲醛 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以98%的产率得到
  参考文献：
  名称：

  Z- and E-selective Horner–Wadsworth–Emmons reactions

  摘要：

  In the present work, we determined and evaluated the stereochemical outcome of the Horner-Wadsworth-Emmons (HWE) reaction of 2-oxoalkylphosphonates with different ester functions (bis(2,2,2-trifluoroethyl), 2,2,2-trifluoroethyl methyl, dimethyl) and side chains (aliphatic, aromatic) with three different aldehydes (benzaldehyde, THP- and PPB-protected Corey aldehydes) under two reaction conditions. The trans protocol is generally used in the E-selective HWE reactions, while cis protocol promotes the Z-selectivity.[GRAPHICS].

  DOI：

  10.1080/00397911.2017.1319487
• 作为产物：
  描述：

  双(2,2,2-三氟乙基)甲基磷酸酯 、 戊酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到2-oxohexyl-phosphonic acid bis(2,2,2-trifluoroethyl)ester
  参考文献：
  名称：

  Organic Compounds

  摘要：

  该发明涉及共轭的二次烯醇衍生物，其生产方法以及包含它们的香料和香水组合物。

  公开号：

  US20100191019A1

文献信息

• A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters
  作者：Katalin Molnár、László Takács、Mihály Kádár、Ferenc Faigl、Zsuzsanna Kardos

  DOI：10.1016/j.tetlet.2015.06.068

  日期：2015.8

  The preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by the acylation of bis(2,2,2-trifluoroethyl) methylphosphonate was re-investigated using esters rather than the sensitive acyl chlorides. Based on our optimization, the best results were achieved when the base (LiHMDS) was added to a solution of the phosphonate and the acylating agent at 90 degrees C. (C) 2015 Elsevier Ltd. All rights reserved.
• ORGANIC COMPOUNDS
  申请人：Givaudan SA

  公开号：EP2178399A1

  公开（公告）日：2010-04-28
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2009009916A1

  公开（公告）日：2009-01-22

  The invention refers to conjugated secondary alkatrienol derivatives, a method of their production and to flavour and perfume compositions comprising them.
• Organic Compounds
  申请人：Granier Thierry

  公开号：US20100191019A1

  公开（公告）日：2010-07-29

  The invention refers to conjugated secondary alkatrienol derivatives, a method of their production and to flavour and perfume compositions comprising them.

  该发明涉及共轭的二次烯醇衍生物，其生产方法以及包含它们的香料和香水组合物。
• <i>Z</i>- and <i>E</i>-selective Horner–Wadsworth–Emmons reactions
  作者：Katalin Molnár、László Takács、Mihály Kádár、Ferenc Faigl、Zsuzsanna Kardos

  DOI：10.1080/00397911.2017.1319487

  日期：2017.7.3

  In the present work, we determined and evaluated the stereochemical outcome of the Horner-Wadsworth-Emmons (HWE) reaction of 2-oxoalkylphosphonates with different ester functions (bis(2,2,2-trifluoroethyl), 2,2,2-trifluoroethyl methyl, dimethyl) and side chains (aliphatic, aromatic) with three different aldehydes (benzaldehyde, THP- and PPB-protected Corey aldehydes) under two reaction conditions. The trans protocol is generally used in the E-selective HWE reactions, while cis protocol promotes the Z-selectivity.[GRAPHICS].