(R,E)-2-methyl-4-phenylbut-3-enoic acid

• 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: (R,E)-2-methyl-4-phenylbut-3-enoic acid
• 英文别名: (E,2R)-2-methyl-4-phenylbut-3-enoic acid
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: WMNSNYYTGUANTL-FCZSHJHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,E)-2-methyl-4-phenylbut-3-enoic acid 在 bis(pyridine)iodonium tetrafluoroborate 、 trifluoroborane diethyl ether 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到(3R,4S,5R)-4-iodo-3-methyl-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective α-Alkenylation of Aldehydes with Boronic Acids via the Synergistic Combination of Copper(II) and Amine Catalysis

  摘要：

  The enantioselective alpha-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of alpha-formyl olefins employing common building blocks for organic synthesis.

  DOI：

  10.1021/ja406356c
• 作为产物：
  描述：

  (R)-(E)-2-methyl-4-phenylbut-3-en-1-ol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以88%的产率得到(R,E)-2-methyl-4-phenylbut-3-enoic acid
  参考文献：
  名称：

  立体选择性全合成10- epi- tirandamycin E

  摘要：

  描述了10-表位-tirandamycin E的立体选择性全合成，采用去对称化方案，闭环复分解（RCM），酸催化的缩酮化，底物控制的二羟基化和Horner-Wadsworth-Emmons烯化为关键反应。

  DOI：

  10.1016/j.tet.2017.01.057

文献信息

• Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Kai Yu、Bukeyan Miao、Wenqi Wang、Armen Zakarian

  DOI：10.1021/acs.orglett.9b00587

  日期：2019.3.15

  Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide–enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

  β，γ-不饱和羧酸的有效不对称烷基化无需事先官能化就可以通过手性锂酰胺实现。对映选择性是由假定的酰胺基-烯二醇锂混合聚集体赋予的，该聚集体发挥就地形成的无痕助剂的作用，允许直接不对称烷基化和简单回收手性试剂。
• Highly Diastereoselective Michael Additions onto Dienyl Bis-Sulfoxides
  作者：Louis Fensterbank、Max Malacria、Franck Brebion、Jean Philippe Goddard

  DOI：10.1055/s-2005-872089

  日期：——

  cinnamaldehyde furnished bis-sulfoxide dienyl derivative 5, a remarkable 1,4-Michael acceptor that can lead in a highly dia­stereoselective manner to vinylcyclopropyl adducts. In a chelating mode of reactivity using a methylcopper reagent, a complete reversal of stereoselectivity is observed giving an enantiopure β,γ-unsaturated methyl ester intermediate that is used in the synthesis of cryptophycin

  报道了制备 (SS,SS)-双(对甲苯基亚磺酰基)甲烷 (4) 的优化程序。将 4 的锂盐缩合到肉桂醛上得到双亚砜二烯基衍生物 5，这是一种非凡的 1,4-迈克尔受体，可以以高度非对映选择性的方式生成乙烯基环丙基加合物。在使用甲基铜试剂的螯合反应模式中，观察到立体选择性的完全逆转，产生了用于合成隐藻素的对映体纯 β,γ-不饱和甲基酯中间体。
• US7385064B1
  申请人：——

  公开号：US7385064B1

  公开（公告）日：2008-06-10
• Enantioselective α-Alkenylation of Aldehydes with Boronic Acids via the Synergistic Combination of Copper(II) and Amine Catalysis
  作者：Jason M. Stevens、David W. C. MacMillan

  DOI：10.1021/ja406356c

  日期：2013.8.14

  The enantioselective alpha-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of alpha-formyl olefins employing common building blocks for organic synthesis.
• Stereoselective total synthesis of 10-epi-tirandamycin E
  作者：Jhillu S. Yadav、Santu Dhara、Debendra K. Mohapatra

  DOI：10.1016/j.tet.2017.01.057

  日期：2017.3

  A stereoselective total synthesis of 10-epi-tirandamycin E is described, employing desymmetrization protocol, ring-closing metathesis (RCM), acid-catalyzed ketalization, substrate controlled dihydroxylation and Horner-Wadsworth-Emmons olefination as key reactions.

  描述了10-表位-tirandamycin E的立体选择性全合成，采用去对称化方案，闭环复分解（RCM），酸催化的缩酮化，底物控制的二羟基化和Horner-Wadsworth-Emmons烯化为关键反应。