(R)-(E)-2-acetoxy-4-(4-methoxyphenyl)-3-butene | 291314-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-(E)-2-acetoxy-4-(4-methoxyphenyl)-3-butene
• 英文别名: (R)-trans-2-acetoxy-4-(4-methoxyphenyl)but-3-ene；(R,E)-4-(4-methoxyphenyl)-3-buten-2-yl acetate；[(E,2R)-4-(4-methoxyphenyl)but-3-en-2-yl] acetate
• CAS: 291314-82-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: FSXWBUZBQJPOBF-ORAHPGNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(E)-2-acetoxy-4-(4-methoxyphenyl)-3-butene 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以95%的产率得到(R,E)-4-(4-methoxyphenyl)but-3-en-2-ol
  参考文献：
  名称：

  Enantioselective synthesis of cis-7-methoxy-calamenene via Claisen rearrangement of an enzymatically resolved allyl alcohol

  摘要：

  An enantioselective synthesis of cis-7-methoxy-calamenene 1 has been accomplished through the following key-steps: (i) enzymatic resolution of the racemic allyl alcohol 3 to furnish the (R)-enantiomer (ee >99%); (ii) Claisen-orthoester rearrangement of 4 to introduce the isopropyl unit on the benzylic position (99% ee); (iii) diastereoselective reduction of dihydronaphthalene derivative 11 to give the cis-isomer 12 (98% de); (iv) regioselective introduction of the formyl group by a Vilsmeier reaction followed by reduction to give 1. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.021
• 作为产物：
  描述：

  (S,E)-4-(4-methoxyphenyl)but-3-en-2-ol 在 Candida antarctica lipase, B 、 hydroxy(triphenyl)silane,oxovanadium 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (R)-(E)-2-acetoxy-4-(4-methoxyphenyl)-3-butene
  参考文献：
  名称：

  通过脂酶-钒组合催化一锅法合成旋光烯丙基酯

  摘要：

  钒-氧代化合物（3或4）与脂肪酶的组合产生了外消旋烯丙醇（1或2）向光学和活性烯丙基酯的区域和对映体转化。在该系统中，钒化合物催化醇的连续外消旋化以及羟基的转位，而脂肪酶则实现化学和对映选择性酯化反应，以实现动态动力学拆分。

  DOI：

  10.1021/ol102053a

文献信息

• Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
  作者：Jun Ho Choi、Yoon Kyung Choi、Yu Hwan Kim、Eun Sil Park、Eun Jung Kim、Mahn-Joo Kim、Jaiwook Park

  DOI：10.1021/jo0355799

  日期：2004.3.1

  tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In

  Aminocyclopentadienyl钌复合物，其可以用作常温消旋催化剂与在动态动力学拆分仲醇的（DKR），脂肪酶是从环戊-2,4- dienimines合成的Ru 3（CO）12，和CHCl 3： [2,3,4,5-PH 4（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上4：R =我-Pr; 5：R = ñ -Pr; 6：R =吨-Bu ），[2,5-ME 2 -3,4--PH 2（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上7：R = i -Pr; 8：R = PH），和[2,3,4,5-PH 4（η 5 -C 4 CNHAr）]的Ru（CO）2 Cl（上9：Ar为p -NO 2 ç 6 ħ 4 ; 10： Ar ＝p- ClC 6 H 4；11：Ar ＝ Ph；12：Ar ＝p- OMeC 6 H 4；13：Ar ＝p- NMe 2 C 6 H 4）。外消旋
• Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions
  作者：Daiji Ikeda、Motoi Kawatsura、Junichi Uenishi

  DOI：10.1016/j.tetlet.2005.07.139

  日期：2005.9

  The palladium catalyzed regio- and diastereo-selective allylic alkylation of (R)-2-acetoxy-4-aryl-3-butene with N-(diphenylmethylidene)glycinate and N-(diphenylmethylidene)alaninate occurred. The stereochemistry was controlled by the use of o-(diphenylphosphino)carboxylic acid, and produced new amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions

  钯催化了（R）-2-乙酰氧基-4-芳基-3-丁烯与N-（二苯基亚甲基）甘氨酸和N-（二苯基亚甲基）丙氨酸的区域和非对映选择性烯丙基烷基化。立体化学通过使用邻-（二苯基膦基）羧酸来控制，并产生了在α和β位置具有邻位手性季碳和叔碳中心的新氨基酸衍生物。
• Continuous‐Flow Dynamic Kinetic Resolution of Racemic Alcohols by Lipase–Oxovanadium Cocatalysis
  作者：Koichi Higashio、Satoko Katsuragi、Dhiman Kundu、Niklas Adebar、Carmen Plass、Franziska Kühn、Harald Gröger、Shuji Akai

  DOI：10.1002/ejoc.202000186

  日期：2020.4.7

  A continuous-flow dynamic kinetic resolution of racemic secondary alcohols was carried out using a single column reactor packed with a mixture of immobilized lipase and an immobilized oxovanadium species, VMPS4. As a result, optically pure esters were produced in 88–92 % yields. Problems encountered in this study were overcome by using fillers that efficiently

  外消旋仲醇的连续流动动态动力学拆分使用填充有固定化脂肪酶和固定化氧钒物质 VMPS4 的混合物的单柱反应器进行。结果，光学纯酯的产率为 88-92%。本研究中遇到的问题通过使用有效的填料来克服
• Dynamic Kinetic Resolution of Allylic Alcohols Mediated by Ruthenium- and Lipase-Based Catalysts
  作者：Donghyun Lee、Eun A. Huh、Mahn-Joo Kim、Hyun Min Jung、Jeong Hwan Koh、Jaiwook Park

  DOI：10.1021/ol006159y

  日期：2000.7.1

  [GRAPHICS]An enzyme-metal combo reaction has been developed for the dynamic kinetic resolution of allylic alcohols in which racemic substrates are transformed by a lipase and a ruthenium complex in the presence of an acyl donor to allylic acetates of high optical purity in over 80% yield.
• One-Pot Synthesis of Optically Active Allyl Esters via Lipase−Vanadium Combo Catalysis
  作者：Shuji Akai、Ryosuke Hanada、Noboru Fujiwara、Yasuyuki Kita、Masahiro Egi

  DOI：10.1021/ol102053a

  日期：2010.11.5

  with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.

  钒-氧代化合物（3或4）与脂肪酶的组合产生了外消旋烯丙醇（1或2）向光学和活性烯丙基酯的区域和对映体转化。在该系统中，钒化合物催化醇的连续外消旋化以及羟基的转位，而脂肪酶则实现化学和对映选择性酯化反应，以实现动态动力学拆分。