丙二酸,[[(1,1-二甲基乙氧基)羰基]氨基]-2-丙烯基-,二乙基酯 | 135722-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 丙二酸,[[(1,1-二甲基乙氧基)羰基]氨基]-2-丙烯基-,二乙基酯
• 英文名称: 2-allyl-2-tert-butoxycarbonylaminomalonic acid diethyl ester
• 英文别名: diethyl 2-(tert-butoxycarbonyl)amino-2-allylmalonate；ethyl 2-Boc-amino-2-ethoxycarbonyl-4-pentenoate；diethyl 2-allyl-2-(Boc-amino)malonate；Diethyl 2-allyl-2-(tert-butoxycarbonylamino)malonate；diethyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-prop-2-enylpropanedioate
• CAS: 135722-55-3
• 化学式: C₁₅H₂₅NO₆
• 分子量: 315.367
• InChiKey: JZHKOSHRDYOGFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙二酸,[[(1,1-二甲基乙氧基)羰基]氨基]-2-丙烯基-,二乙基酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 allyl-amino-malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of novel and conformationally constrained bridged amino acids as compact modules for drug discovery

  摘要：

  As novel scaffolds with rigid inherent three-dimensional conformation, the bridged amino acid building blocks containing both morpholine and pyrrolidine motifs, 2-oxa-5-azabicyclo[2.2.1]heptane-4-carboxylic acid 1 and 3-oxa-8-azabicyclo[3.2.1Ioctane-5-carboxylic acid 2, were first synthesized as compact modules for future applications in the optimization of physicochemical and pharmacokinetic properties of drug candidates in drug discovery. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.097
• 作为产物：
  描述：

  氨基丙二酸二乙酯盐酸盐 在 sodium hydroxide 、 sodium 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 28.0h， 生成 丙二酸,[[(1,1-二甲基乙氧基)羰基]氨基]-2-丙烯基-,二乙基酯
  参考文献：
  名称：

  Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids

  摘要：

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

  DOI：

  10.1021/jo00055a022

文献信息

• Generation and Intermolecular Additions of Pyridylmethyl Radicals
  作者：Samir Zard、Zorana Ferjancic、Béatrice Quiclet-Sire

  DOI：10.1055/s-2008-1067198

  日期：2008.9

  2-, 3-, or 4-Pyridylmethyl radicals can be made to add to nonactivated alkenes to give a variety of otherwise inaccessible pyridine derivatives. Bicyclic structures can be obtained by combining the radical addition with ionic ring-closure steps.

  2-、3-或4-吡啶基甲基自由基可以通过加成反应添加到非活化烯烃上，形成多种原本难以获得的吡啶衍生物。通过将自由基加成与离子环合步骤相结合，可以获得双环结构。
• Nonenzymatic Enantioselective Monoacetylation of Prochiral 2-Protectedamino-2-alkyl-1,3-propanediols Utilizing a Chiral Sulfonamide−Zn Complex Catalyst
  作者：Takashi Honjo、Michiyasu Nakao、Shigeki Sano、Motoo Shiro、Kentaro Yamaguchi、Yoshihisa Sei、Yoshimitsu Nagao

  DOI：10.1021/ol063063g

  日期：2007.2.1

  presence of 5 mol % of chiral sulfonamide-Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.

  [结构：见正文]用Et（2）Zn处理手性磺酰胺可定量得到其Zn络合物，然后通过X射线晶体学分析确定其结构。前手性N-Boc-2-氨基-2-烷基-1,3-丙二醇与Ac（2）O在5 mol％手性磺酰胺-锌络合物催化剂存在下的反应在70-92中提供了相应的手性单乙酰基产物具有70-88％ee值的％产率。在CSI-MS分析的基础上，提出了前手性1,3-丙二醇催化单乙酰化的机理。
• Epoxy amino acids produced from allylglycines intramolecularly cyclised to yield four stereoisomers of 4-hydroxyproline derivatives
  作者：Suvratha Krishnamurthy、Toru Arai、Kanae Nakanishi、Norikazu Nishino

  DOI：10.1039/c3ra45184d

  日期：——

  Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m-chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating

  使用枯草杆菌蛋白酶或酰基转移酶可有效拆分2-氨基-4-戊烯酸（烯丙基甘氨酸）的衍生物。与对映体纯的氨基酸的侧链不饱和键叔丁氧羰基（BOC）保护顺利与环氧化米氯过苯甲酸。当氨基的Boc保护被去除时，氨基分子内攻击侧链环氧化物，生成具有五元环的化合物：4-羟基脯氨酸衍生物。通过环化反应形成了两个非对映异构产物，例如（2 S，4 S）-4-羟基脯氨酸苄基酯（cis - 8）和（2 S，4 R）-4-羟基脯氨酸苄酯（反式- 8）从（2形成小号） -氨基与侧链的环氧化物酸。化合物（2小号，4小号）-4-羟基脯氨酸苄酯（顺式- 8）转化为内酯（顺式-羟基脯氨酸内酯，10）具有去除苄醇。所述顺式-conformation是为分子内的酯交换反应是必不可少的; 事实上，观察到的无内酯形成的反式异构体（反式- 8）。顺式羟脯氨酸内酯与甘油三酯的分离与难于分离顺式和反式羟脯氨酸衍生物相反，反式异构体羟脯氨酸苄基
• Oxidation of functional olefines: Synthesis of protected amino acids bearing a terminal α-hydroxyketo group
  作者：Katerine David、Alfred Greiner、Jacques Goré、Bernard Cazes

  DOI：10.1016/0040-4039(96)00570-9

  日期：1996.5

  The osmium trichloride-catalyzed oxidation with peracetic acid of olefinic compounds bearing a protected α-amino acid group leads to α-ketol amino acid precursors related to the 5-Hydroxy-4-Oxo-Norvaline antibiotic.

  三氯化bearing催化带有保护的α-氨基酸基团的烯烃化合物的过氧乙酸氧化，可生成与5-羟基-4-氧代-Norvaline抗生素有关的α-酮醇氨基酸前体。
• Copper(I) Photocatalyzed Bromonitroalkylation of Olefins: Evidence for Highly Efficient Inner‐Sphere Pathways
  作者：Alexander Reichle、Magdalena Koch、Hannes Sterzel、Lea‐Joy Großkopf、Johannes Floss、Julia Rehbein、Oliver Reiser

  DOI：10.1002/anie.202219086

  日期：——

  Photocatalytic bromonitroalkylations of activated and unactivated olefins with broad scope become possible in the presence of CuI-photocatalysts. The key to success for this transformation is the highly efficient interaction of CuII with radical intermediates, which can even outperform a highly favorable cyclization of a transient to a persistent radical.

  在 Cu I -光催化剂存在下，具有广泛范围的活化和未活化烯烃的光催化溴硝基烷基化成为可能。这种转化成功的关键是 Cu II与自由基中间体的高效相互作用，它甚至可以胜过从瞬态自由基到持久自由基的高度有利的环化。