Ethyl 2-[(2,4-dichlorophenyl)-[(2-methylpropan-2-yl)oxycarbonyloxy]methyl]prop-2-enoate | 1381860-19-0

• 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: Ethyl 2-[(2,4-dichlorophenyl)-[(2-methylpropan-2-yl)oxycarbonyloxy]methyl]prop-2-enoate
• CAS: 1381860-19-0
• 化学式: C₁₇H₂₀Cl₂O₅
• 分子量: 375.249
• InChiKey: GTCRJUQBZCAXGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[(2,4-dichlorophenyl)-[(2-methylpropan-2-yl)oxycarbonyloxy]methyl]prop-2-enoate 、 3-氰苯酞 在 N-[3,5-二(三氟甲基)苯基]-N'-[(1S,2R)-2-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]-1-[(二苯基膦基)甲基]丙基]硫脲 作用下， 以99%的产率得到ethyl 2-((R)-((S)-1-cyano-3-oxo-1,3-dihydroisobenzofuran-1-yl)-(2,4-dichlorophenyl)methyl)acrylate
  参考文献：
  名称：

  Asymmetric Synthesis of Dihydronaphthoquinones Containing Adjacent Stereocenters via a Sulfa-Michael Addition Triggered Ring-Expansion Approach

  摘要：

  A novel asymmetric synthetic approach for the construction of enantioenriched functionalized dihydroquinones incorporating adjacent quaternary and tertiary stereocenters has been reported, in which enantioenriched 3-allylic phthalides engaged in an unprecedented sulfa-Michael addition-triggered Stereoselective ring-expansion reaction, and furnished the desired sulfur-incoporated dihydronaphthoquinones with high stereoselectivity.

  DOI：

  10.1021/acs.joc.5b00502
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 Ethyl 2-[(2,4-dichlorophenyl)-[(2-methylpropan-2-yl)oxycarbonyloxy]methyl]prop-2-enoate
  参考文献：
  名称：

  α-氨基酸衍生酯和 MBH 碳酸酯的区域选择性开关用于合成烯丙基取代的二氢唑酮

  摘要：

  烯丙基吖内酯在潜在的生物活性和合成应用方面具有非常重要的意义。由于制药工业对α-氨基酸衍生物的兴趣日益浓厚，发现烯丙基吖内酯的合成策略非常重要。在此，我们建立了α-氨基酸衍生的酯和MBH碳酸酯的无过渡金属区域选择性开关，其表现出广泛的反应范围和良好的反应产率。对照反应表明碱和溶剂对于区域选择性都很重要。

  DOI：

  10.1021/acs.joc.3c02648

文献信息

• Enantioselective synthesis of spirocyclic cyclopentenes: asymmetric [3+2] annulation of 2-arylideneindane-1,3-diones with MBH carbonates derivatives catalyzed by multifunctional thiourea–phosphines
  作者：Fangle Hu、Yin Wei、Min Shi

  DOI：10.1016/j.tet.2012.07.013

  日期：2012.9

  The [3+2] annulation reactions of 2-arylideneindane-1,3-diones with Morita–Baylis–Hillman (MBH) carbonates proceeded smoothly in the presence of multifunctional thiourea–phosphines to produce the corresponding quaternary carbon centered spirocyclic cyclopentenes in moderate yields, with high diastereoselectivities and enantioselectivities under mild conditions. The plausible reaction has been also

  在多功能硫脲-膦的存在下，2-芳基亚乙基-1,3-二酮与Morita–Baylis–Hillman（MBH）碳酸盐的[3 + 2]环化反应顺利进行，从而以中等收率产生了相应的季碳中心的螺环式环戊烯在温和条件下具有较高的非对映选择性和对映选择性。在先前的文献基础上，也对合理的反应进行了讨论。
• Asymmetric P−C Bond Formation: Diastereoselective Synthesis of Adjacent P,C-Stereogenic Allylic Phosphorus Compounds
  作者：Peizhong Xie、Lei Guo、Lanlan Xu、Teck-Peng Loh

  DOI：10.1002/asia.201600108

  日期：2016.5.6

  A novel catalytic asymmetric P−C bond formation between phosphinates/phosphine oxide and allylic carbonates was developed. This methodology could not only afford a variety of functionalized adjacent P,C‐stereogenic phosphorus compounds in high yields with high regio‐ and diastereoselectivities but also provide an alternative strategy to access enantiomerically enriched (SP)‐phosphinates through kinetic

  开发了在次膦酸酯/氧化膦与烯丙基碳酸酯之间形成新型催化不对称P-C键的方法。这种方法不仅可以提供高产率，具有高区域和非对映选择性的多种功能化的邻位P，C-立体异构磷化合物，而且还提供了一种通过动力学拆分获得对映体富集的（S P）-次膦酸盐的替代策略。
• Phosphine‐Mediated Domino Benzannulation Strategy for the Construction of Highly Functionalized Multiaryl Skeletons
  作者：Peizhong Xie、You Huang、Ruyu Chen

  DOI：10.1002/chem.201200305

  日期：2012.6.11

  A skeleton crew: A phosphine‐mediated domino benzannulation strategy was developed for the synthesis of multiaryl skeletons (see scheme). A wide range of aromatic compounds and functional groups can be assembled into a multiaryl molecule through a core domino process.

  骨架工作人员：开发了膦介导的多米诺苯环化策略以合成多芳基骨架（请参见方案）。通过核心的多米诺骨牌过程，可以将各种各样的芳族化合物和官能团组装成一个多芳基分子。
• Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides
  作者：Fangrui Zhong、Jie Luo、Guo-Ying Chen、Xiaowei Dou、Yixin Lu

  DOI：10.1021/ja303115m

  日期：2012.6.20

  Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.
• Asymmetric Construction of Functionalized Bicyclic Imides via [3 + 2] Annulation of MBH Carbonates Catalyzed by Dipeptide-Based Phosphines
  作者：Fangrui Zhong、Guo-Ying Chen、Xiaoyu Han、Weijun Yao、Yixin Lu

  DOI：10.1021/ol301647g

  日期：2012.7.20

  A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of L-Thr-L-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.