(E)-2-(3-(1-naphthyl)-allyl) malonic acid dimethyl ester | 212777-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(3-(1-naphthyl)-allyl) malonic acid dimethyl ester
• 英文别名: 2-[(3-naphthalen-1-yl)allyl]-malonic acid dimethyl ester；dimethyl 3-(1-naphthyl)-2-propenylmalonate；dimethyl 2-[(E)-3-naphthalen-1-ylprop-2-enyl]propanedioate
• CAS: 212777-61-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: SEXJSTSURHGGES-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(1'-naphthyl)-allylalcohol 在 吡啶 、 2,2'-联吡啶 、 6-C7H8)> 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (E)-2-(3-(1-naphthyl)-allyl) malonic acid dimethyl ester
  参考文献：
  名称：

  Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation

  摘要：

  Tungsten-bipyridine complexes, generated in situ, catalyse the allylic alkylation of isocinnamyl methyl carbonate by dimethyl sodiomalonate [NaCH(CO2CH3)(2)] with complete syn-stereoselectivity. When para substituted aryl-allyl methyl carbonates are employed, the regioselectivity correlates with Swain-Lupton parameters. Cross-over experiments demonstrate that the reactions do not procede via the conventional [M(0)] --> [M(II) allyl](+) --> [M(0) allyl-Nu] catalytic cycle.

  DOI：

  10.1016/0040-4020(95)00481-m

文献信息

• Chiral Bis(N-sulfonylamino)phosphine- and TADDOL-Phosphite-Oxazoline Ligands: Synthesis and Application in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1002/adsc.200404168

  日期：2005.1

  has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts

  制备了一系列N，P-配体，其包含手性恶唑啉环和嵌入在二氮磷吡啶环中的双（N-磺酰基氨基）膦基或衍生自TADDOL的环状亚磷酸酯基作为第二手性单元。这些模块化配体易于从手性氨基醇和手性1,2-二胺或TADDOLs合成。发现衍生自这些配体的钯和铱配合物分别是对映选择性烯丙基烷基化和烯烃氢化的有效催化剂。
• New Ligands for Regio- and Enantiocontrol in Pd-Catalyzed Allylic Alkylations
  作者：Roger Prétôt、Andreas Pfaltz

  DOI：10.1002/(sici)1521-3773(19980216)37:3<323::aid-anie323>3.0.co;2-t

  日期：1998.2.16

  The branched, chiral products 1 are formed preferentially in the allylic alkylations in Equation (1) when the Pd catalyst contains the P,N ligand L* or derivatives thereof. The ligands are readily synthesized from commercially available precursors.

  当Pd催化剂包含P，N配体L *或其衍生物时，优选在等式（1）的烯丙基烷基化反应中形成支链手性产物1。配体易于从可商购的前体合成。
• Chiral Bis(<i>N</i>-tosylamino)phosphine- and TADDOL-Phosphite-Oxazolines as Ligands in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1055/s-1999-2939

  日期：1999.11

  A series of P,N-ligands containing a chiral oxazoline ring and a chiral bis(N-tosylamino)phosphine group derived from a 1,2-diamine or a chiral cyclic phosphite group derived from TADDOL has been prepared. These compounds proved to be efficient ligands for enantiocontrol of palladium-catalyzed allylic alkylations and iridium-catalyzed hydrogenations of olefins.

  一系列含手性噁唑啉环和手性双(N-甲苯磺酰氨基)膦基团（源自1,2-二胺）或手性环状亚磷酸酯基团（源自TADDOL）的P,N配体已被合成。这些化合物被证明是钯催化的烯丙基烷基化反应和铱催化的烯烃氢化反应中高效的手性控制配体。
• Modular Furanoside Diphosphite Ligands for Pd-Catalyzed Asymmetric Allylic Substitution Reactions: Scope and Limitations
  作者：Montserrat Diéguez、Oscar Pàmies、Carmen Claver

  DOI：10.1002/adsc.200505013

  日期：2005.7

  We have synthesized a library of furanoside diphosphite ligands for the Pd-catalyzed allylic substitution reactions of acyclic and cyclic allylic esters. The library has been designed to rapidly screen the ligands to uncover their important structural features and to determine the scope of diphosphite ligands in these catalytic reactions. After the systematic variation of the sugar backbone, the substituent

  我们已经合成了呋喃糖苷二亚磷酸酯配体的文库，用于Pd催化的无环和环状烯丙基酯的烯丙基取代反应。该文库旨在快速筛选配体以揭示其重要的结构特征，并确定这些催化反应中二亚磷酸酯配体的范围。在系统地改变了糖主链，C-5处的取代基和亚磷酸酯部分后，发现二亚磷酸酯配体4c在受阻（S1）和不受阻（S2 - S5）底物的Pd催化不对称烯丙基取代中是最佳的。，产生高活性[TOFs最高> 3000 mol×（mol×h）-1]和对映选择性（ee高达99％）。此外，对文库的筛选使我们能够找到其他合适的配位体，用于受阻双取代线性底物S1（配体1b – d，g和4b，d，g）和无阻环底物S3 – S5（配体6c和7c）。
• New Carbohydrate-Based Phosphite-Oxazoline Ligands as Highly Versatile Ligands for Palladium-Catalyzed Allylic Substitution Reactions
  作者：Yvette Mata、Montserrat Diéguez、Oscar Pàmies、Carmen Claver

  DOI：10.1002/adsc.200505192

  日期：2005.12

  We have designed and synthesized a new family of readily available phosphite-oxazoline ligands for Pd-catalyzed asymmetric allylic substitution reactions. These ligands can be tuned in two regions to explore their effect on catalytic performance. By carefully selecting the ligand components, we obtained high enantioselectivities in the Pd-catalyzed allylic substitution in substrates with different

  我们已经设计和合成了新的易于使用的亚磷酸酯-恶唑啉配体家族，用于Pd催化的不对称烯丙基取代反应。这些配体可以在两个区域进行调节，以探索它们对催化性能的影响。通过仔细选择配体成分，我们在具有不同空间特性的底物中钯催化的烯丙基取代中获得了高对映选择性