(R)-ethyl 4-(4-chlorophenyl)-2-hydroxypent-4-enoate

• 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)-ethyl 4-(4-chlorophenyl)-2-hydroxypent-4-enoate
• 英文别名: ethyl (2R)-4-(4-chlorophenyl)-2-hydroxypent-4-enoate
• 化学式: C₁₃H₁₅ClO₃
• 分子量: 254.713
• InChiKey: FJAZGJHQKBLKOH-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛酸乙酯 、 对氯甲基苯乙烯 在 indium(III) triflate 、 2,6-双[(3aR,8aS)-(+)-8H-茚[1,2-d]恶唑啉-2-基]吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 以95%的产率得到(R)-ethyl 4-(4-chlorophenyl)-2-hydroxypent-4-enoate
  参考文献：
  名称：

  In(III)-PyBox 复合物催化的高对映选择性羰基-烯反应

  摘要：

  描述了由 In(III)-pybox 催化的高度对映选择性羰基 - 烯反应。1,1-二取代烯烃和 1,1,2-三取代烯烃均能顺利进行，以高达 97% 的高产率得到 ene 产物，并且具有优异的非对映选择性和对映选择性分别高达 >99:1 和 99%。

  DOI：

  10.1021/ja807501a

文献信息

• Enantioselective turnover in glyoxylate-ene reactions catalyzed by chiral copper complexes
  作者：Manoj K. Pandey、Alakesh Bisai、Vinod K. Singh

  DOI：10.1016/j.tetlet.2005.11.159

  日期：2006.2

  The catalytic, enantioselective carbonyl-ene reaction of ethyl glyoxylate with α-methylstyrene and 4-halo-α-methylstyrene has been investigated in the presence of copper triflate–bisoxazoline complexes. The reaction proceeded smoothly to give γ,δ-unsaturated-α-hydroxy esters in moderate to good yields and with excellent enantioselectivity (up to 100% ee). A hypothesis has been provided to explain the

  在三氟甲磺酸铜-双恶唑啉铜配合物的存在下，研究了乙醛酸乙酯与α-甲基苯乙烯和4-卤代-α-甲基苯乙烯的催化，对映选择性羰基-烯反应。反应平稳进行，以中等至良好的产率和优异的对映选择性（至多100％ee）得到γ，δ-不饱和-α-羟基酯。提供了一个假设来解释反应中对映选择性的逆转。
• Enantioselective carbonyl–ene reaction on BINOLate/titanium catalyst encapsulated in magnetic nanoreactors
  作者：Xiao Liu、Shiyang Bai、Yan Yang、Bo Li、Bing Xiao、Can Li、Qihua Yang

  DOI：10.1039/c2cc17950d

  日期：——

  An asymmetric multicomponent catalyst, BINOLate/titanium, successfully encapsulated in the nanocages of mesoporous silicas exhibits much higher activity than the homogeneous counterpart in quasi solvent-free enantioselective carbonyl-ene reaction, owing to the confinement effect of the nanoreactor.

  由于纳米反应器的限制作用，在准无溶剂对映选择性羰基-烯反应中，成功封装在介孔二氧化硅纳米笼中的不对称多组分催化剂BINOLate /钛表现出比均相对应物高得多的活性。
• Significant counterion effect of the In(III)–pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate
  作者：Jun-Feng Zhao、Teguh-Budiono W. Tjan、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2010.06.066

  日期：2010.10

  A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of alpha-methyl styrenes are tolerated in this reaction. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective glyoxylate-ene reaction using a novel spiro bis(isoxazoline) ligand in copper catalysis
  作者：Kazuhiko Wakita、Gan B. Bajracharya、Midori A. Arai、Shinobu Takizawa、Takeyuki Suzuki、Hiroaki Sasai

  DOI：10.1016/j.tetasy.2007.02.004

  日期：2007.2

  Novel chiral spiro bis(isoxazoline) ligands 3 and 4 are synthesized from an optically active olefin. The Cu(II)-spiro bis(isoxazoline) complex prepared in situ from Cu(OTf)(2) and 3 promoted the glyoxylate-ene reaction in high yield and moderate enantioselectivity (up to 70%). (c) 2007 Published by Elsevier Ltd.