allyl 2,2-diphenylglycinate | 946164-43-8

• 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: allyl 2,2-diphenylglycinate
• 英文别名: Prop-2-enyl 2-amino-2,2-diphenylacetate；prop-2-enyl 2-amino-2,2-diphenylacetate
• CAS: 946164-43-8
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: RTKTZBFLVSKPLL-UHFFFAOYSA-N

物化性质

• 沸点：
  399.6±37.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  allyl 2,2-diphenylglycinate 在 二苯基膦基二茂铁 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 4 A molecular sieve 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 25.5h， 生成 ethyl N-(diphenylmethylene)-2-amino-4-pentenoate
  参考文献：
  名称：

  C−C Bond-Forming Reactions via Pd-Mediated Decarboxylative α-Imino Anion Generation

  摘要：

  alpha-Imino anions are generated under neutral reaction conditions via a Pd-mediated decarboxylation of allyl diphenylglycinate imines with concomitant formation of a pi-allylpalladium species. The resulting delocalized anion can attack the pi-allyl-Pd(II) species or be intercepted by aldehydes to afford homoallylic amines or protected 1,2-amino alcohols, respectively.

  DOI：

  10.1021/ol071080f
• 作为产物：
  描述：

  2,2-二苯基甘氨酸 在 sodium hydroxide 、 碘代三甲硅烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 allyl 2,2-diphenylglycinate
  参考文献：
  名称：

  C−C Bond-Forming Reactions via Pd-Mediated Decarboxylative α-Imino Anion Generation

  摘要：

  alpha-Imino anions are generated under neutral reaction conditions via a Pd-mediated decarboxylation of allyl diphenylglycinate imines with concomitant formation of a pi-allylpalladium species. The resulting delocalized anion can attack the pi-allyl-Pd(II) species or be intercepted by aldehydes to afford homoallylic amines or protected 1,2-amino alcohols, respectively.

  DOI：

  10.1021/ol071080f

文献信息

• [EN] COMPOSITIONS COMPRISING ENZYME CLEAVABLE LINKER PLATFORMS AND CONJUGATES THEREOF<br/>[FR] COMPOSITIONS COMPRENANT DES PLATEFORMES DE LIEURS CLIVABLES PAR UNE ENZYME ET LEURS CONJUGUÉS
  申请人：UNIV DANMARKS TEKNISKE

  公开号：WO2020260597A1

  公开（公告）日：2020-12-30

  The present invention relates to a cleavable linker platform. In particular, the invention relates to construction of an enzyme cleavable linker platform conjugated to a drug or a diagnostically relevant compound, a biomolecule, and an enzyme cleavable group, for which cleavage of the enzyme cleavable group leads to release of the drug or diagnostically relevant compound.

  本发明涉及可切割连接剂平台。具体而言，本发明涉及构建一个与药物或诊断相关化合物、生物分子以及可切割酶基团共轭的酶可切割连接剂平台，其中酶可切割基团的切割导致药物或诊断相关化合物的释放。
• Palladium-Catalyzed Decarboxylative Generation and Asymmetric Allylation of α-Imino Anions
  作者：Xiaoyan Qian、Pengfei Ji、Chang He、Jean-Olivier Zirimwabagabo、Michelle M. Archibald、Andrew A. Yeagley、Jason J. Chruma

  DOI：10.1021/ol502693r

  日期：2014.10.3

  A palladium-catalyzed asymmetric decarboxylative allylic alkylation of allyl 2,2-diphenylglycinate imines using (S,S)-f-binaphane as a chiral supporting ligand has been developed. This transformation allows for decarboxylative generation and enantioselective allylation of nonenolate α-imino (2-azaallyl anions) to afford α-aryl homoallylic imines.

  钯催化的不对称脱羧烯丙基使用（烯丙基2,2- diphenylglycinate亚胺烷基化S，S） - ˚F -binaphane作为手性支持配体已被开发。该转化允许壬烯酸酯α-亚氨基（2-氮杂烯丙基阴离子）的脱羧生成和对映选择性烯丙基化，以提供α-芳基均烯丙基亚胺。
• Exploring the Steric and Electronic Factors Governing the Regio- and Enantioselectivity of the Pd-Catalyzed Decarboxylative Generation and Allylation of 2-Azaallyl Anions
  作者：Shuaifei Wang、Xiaoyan Qian、Yuanyu Chang、Jiayue Sun、Xiujing Xing、Wendy F. Ballard、Jason J. Chruma

  DOI：10.1021/acs.joc.8b00491

  日期：2018.4.6

  The impact of the steric and electronic factors in both the para-substituted benzaldimine and 2,2-diarylglycine components on the regioselectivity and enantioselectivity of the palladium-catalyzed decarboxylative allylation of allyl 2,2-diarylglycinate aryl imines was explored. These studies revealed that using 2,2-di(2-methoxyphenyl)glycine as the amino acid linchpin allowed for the exclusive synthesis

  立体和电子因素对参数的影响探索了取代的苯甲二胺和2,2-二芳基甘氨酸组分对钯催化的2,2-二芳基甘氨酸烯丙基烯丙基芳基亚胺的钯催化的脱羧烯丙基化的区域选择性和对映体选择性。这些研究表明，使用2，2-二（2-甲氧基苯基）甘氨酸作为氨基酸发夹可以独立于亚胺部分的性质以期望的高收率独家合成所需的均烯丙基二苯甲酮亚胺区域异构体。然而，与涉及相应的2，2-二苯基甘氨酸烯丙基烯丙基亚胺的转化相比，所得的对映体比率略有降低，但这在产率和区域选择性的增加上得到了平衡。总的来说，这些研究提出了2-氮杂烯丙基阴离子的高度区域选择性功能化的一般策略。
• Nickel-Catalyzed Decarboxylative Generation and Asymmetric Allylation of 2-Azaallyl Anions
  作者：Chenlu Liu、Changfeng Deng、Han Yang、Xiaoyan Qian、Shaojian Tang、Michal Poznik、Jason J. Chruma

  DOI：10.1021/acs.joc.9b01293

  日期：2019.8.16

  The first nickel-catalyzed asymmetric decarboxylative allylation (DcA) of allyl 2,2-diarylglycinate imines is reported. This transformation utilizes a chiral ferrocenyl bidentate ligand and a Ni(0) precatalyst to mediate the decarboxylative generation and asymmetric allylation of 2-azaallyl anions, affording α-aryl homoallylic imines in modest-to-high yields and moderate-to-high enantiomeric ratios

  报道了2，2-二芳基甘氨酸烯丙基烯丙基亚胺的第一个镍催化的不对称脱羧烯丙基化（DcA）。此转化利用手性二茂铁二齿双齿配体和Ni（0）预催化剂介导2-氮杂烯丙基阴离子的脱羧生成和不对称烯丙基化，以中等至高收率和中等至高对映体比率提供α-芳基均烯丙基亚胺。 。与我们先前报道的类似的Pd介导的实验方案相比，所产生的Ni催化的转化过程被证明不那么普遍，但是就C–C键形成的区域和对映选择性而言，它仍然表现出一定的优势。
• Tandem C−C Bond-Forming Processes: Interception of the Pd-Catalyzed Decarboxylative Allylation of Allyl Diphenylglycinate Imines with Activated Olefins
  作者：Andrew A. Yeagley、Melissa A. Lowder、Jason J. Chruma

  DOI：10.1021/ol901745x

  日期：2009.9.3

  Interception of the Pd-catalyzed decarboxylative allylation of allyl diphenylglycinate Imines with appropriately functionalized Michael acceptors, followed by Heck cyclization, allows for the efficient construction of relatively complex organoamine frameworks in one reaction vessel. The initial intercepted decarboxylative allylation Is remarkably insensitive toward solvent and catalyst, typically proceeding under ambient conditions.