5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid | 1436871-90-7

• 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: 5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid
• CAS: 1436871-90-7
• 化学式: C₂₆H₁₈Cl₂O₂
• 分子量: 433.334
• InChiKey: OXGLYIJCKBIDNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid 在 Hydroquinone 1,4-phthalazinediyl diether 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 15.25h， 以92%的产率得到(R,E)-5-(bromo(4-chlorophenyl)methylene)-3-(3-(4-chlorophenyl)prop-2-ynyl)-3-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective, Desymmetrizing Bromolactonization of Alkynes

  摘要：

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.

  DOI：

  10.1021/ja402910d
• 作为产物：
  描述：

  苯乙酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 sodium hydride 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid
  参考文献：
  名称：

  Enantioselective, Desymmetrizing Bromolactonization of Alkynes

  摘要：

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.

  DOI：

  10.1021/ja402910d

文献信息

• An Enantioselective Iodolactonization/Cross-Coupling Protocol for the Synthesis of Highly Substituted Enol Lactones
  作者：Christoph Fricke、Michael Wilking、Constantin G. Daniliuc、Ulrich Hennecke

  DOI：10.1002/ejoc.201800642

  日期：2018.6.29

  A sequence of catalytic enantioselective iodolactonization followed by Palladium‐catalyzed cross‐coupling provides rapid access to highly substituted enol lactones. With DHQD2PHAL as catalyst, moderate to very good enantioselectivities in the iodolactonization step can be obtained.

  一系列的催化对映选择性碘内酯化，然后进行钯催化的交叉偶联，可快速获得高度取代的烯醇内酯。用DHQD 2 PHAL作为催化剂，可以在碘内酯化步骤中获得中等到非常好的对映选择性。
• Monomeric Cinchona Alkaloid-Based Catalysts for Highly Enantioselective Bromolactonisation of Alkynes
  作者：Michael Wilking、Constantin G. Daniliuc、Ulrich Hennecke

  DOI：10.1002/chem.201604003

  日期：2016.12.19

  The cinchona alkaloid dimer (DHQD)2PHAL has been shown to be a broadly applicable catalyst for asymmetric halogenations. However, this catalyst does not have to be dimeric and a class of monomeric quinidine and quinine‐derived catalysts was prepared, often showing superior selectivity in bromolactonisations of terminal alkynoic acids. Mechanistic investigations show that these organocatalysts act as

  金鸡纳生物碱二聚体（DHQD）2 PHAL已被证明是广泛用于不对称卤化的催化剂。但是，该催化剂不必是二聚体，而是制备了一类单体奎尼丁和奎宁衍生的催化剂，通常在末端炔酸的溴内酯化反应中显示出较高的选择性。机理研究表明，这些有机催化剂充当主体分子，可以作为具有实质性结合常数的客体结合基于羧酸的底物。基于这些发现，提出这类催化剂本质上是双官能的，在亲电子卤化反应中活化卤化剂以及亲核试剂。