N-Cbz allylglycine methyl ester | 106928-49-8

• 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
• 英文名称: N-Cbz allylglycine methyl ester
• 英文别名: Methyl 2-{[(benzyloxy)carbonyl]amino}pent-4-enoate；methyl 2-(phenylmethoxycarbonylamino)pent-4-enoate
• CAS: 106928-49-8
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: RKNNPGXXWNQYKS-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±42.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Cbz allylglycine methyl ester 在 三甲基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Highly diastereoselective synthesis of β-amino alcohols

  摘要：

  若干取代的β-氨基醇1通过高度灵活的新型中间体8b以对映选择性的方式合成，涉及N-酰基氮鎓离子和Weinreb酰胺化学的组合。

  DOI：

  10.1039/b108254j
• 作为产物：
  描述：

  甲基-2-Boc-氨基-4-戊烯酸 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 N-Cbz allylglycine methyl ester
  参考文献：
  名称：

  Selective transformation of N--butoxycarbonyl group into n-alkoxy-carbonyl group n-carboxylate ion equivalent

  摘要：

  DOI：

  10.1016/s0040-4039(01)80883-2

文献信息

• Tertiary-butyldimethylsilyl carbamate derivative and process for
  申请人：Suntory Limited

  公开号：US04837349A1

  公开（公告）日：1989-06-06

  A t-butyldimethylsilyl carbamate derivative and a process for producing the same are disclosed. Tertiary-butyldimethylsilyl carbamate derivatives having the following general formula (1) are intermediates for the production of a variety of carbamate esters that can be extensively used as drugs acting on the central nervous system or circulatory organs, as agrichemicals (e.g. insecticides and herbicides), or as antimicrobial agents; a process capable of economical and efficient production of such intermediates is also disclosed: ##STR1## where R.sup.1 is an alkyl group having 1-3 carbon atoms or a hydrogen atom; R.sup.2 is ##STR2## (where R.sup.3 is a hydrogen atom, an alkyl, alkenyl or aralkyl group having 1-10 carbon atoms, each of which groups may be substituted by a hydroxyl group, a t-butyldimethylsilyloxy group, a methylthio group, a lower alkoxycarbonyl group, a lower alkoxy group, an indolyl group or an imidazolyl group; R.sup.4 is a lower alkoxycarbonyl group, an N-alkylamido group having 2-6 carbon atoms, an O-tetrahydropyranylthr eonine methyl ester amido residue, an O-t-butyldimethylsilylthreonine methyl ester amido residue, a threonine methyl ester amido residue or --(CH.sub.2).sub.n --COOR.sup.5 (where n is an integer of 1-3 and R.sup.5 is a lower alkyl group), provided that R.sup.3 combines with R.sup.4 to form a cyclopentyl group, a cyclohexyl group, a tetrahydrofuranyl group or a dioxanyl group, these rings being optionally substituted by a lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonylmethyl group); and R.sup.1 and R.sup.2, when taken together, form a 4- or 5-membered carbon ring, which may be substituted by a lower alkoxycarbonyl group or a t-butyldimethylsilyloxycarbonyl group.

  揭示了一种t-叔丁基二甲基硅烷基氨基甲酸酯衍生物及其生产方法。具有以下一般式（1）的三叔丁基二甲基硅烷基氨基甲酸酯衍生物是生产各种氨基甲酸酯的中间体，这些氨基甲酸酯可以广泛用作作用于中枢神经系统或循环器官的药物、农药（例如杀虫剂和除草剂）或抗微生物剂；还揭示了一种能够经济高效地生产这种中间体的方法：其中R.sup.1是具有1-3个碳原子的烷基基团或氢原子；R.sup.2是##STR2##（其中R.sup.3是氢原子、具有1-10个碳原子的烷基、烯基或芳基基团，每个基团可能被羟基、t-叔丁基二甲基硅氧基基团、甲硫基团、较低的烷氧羰基基团、较低的烷氧基团、吲哚基团或咪唑基团取代；R.sup.4是较低的烷氧羰基基团、具有2-6个碳原子的N-烷基酰胺基团、O-四氢吡喃基缬氨酸甲酯酰胺残基、O-t-叔丁基二甲基硅基缬氨酸甲酯酰胺残基、缬氨酸甲酯酰胺残基或--(CH.sub.2).sub.n --COOR.sup.5（其中n是1-3的整数，R.sup.5是较低的烷基基团），前提是R.sup.3与R.sup.4结合形成环戊基团、环己基团、四氢呋喃基团或二氧杂环己基团，这些环可选择地被较低的烷基基团、较低的烯基基团、较低的烷氧羰基基团或较低的烷氧羰基甲基基团取代）；以及当R.sup.1和R.sup.2结合在一起时，形成一个4-或5-成员碳环，该环可被较低的烷氧羰基基团或t-叔丁基二甲基硅氧羰基基团取代。
• Synthesis of α-amino acids with β,γ-unsaturated side chains
  作者：Arlindo L. Castelhano、Stephen Horne、Gregg J. Taylor、Roland Billedeau、Allen Krantz

  DOI：10.1016/s0040-4020(01)86051-8

  日期：1988.1

  α-Amino acids with allenyl, vinyl, and acetylenic side chains can be synthesized using non-enolate based strategies. The ester enolate-Claisen rearrangement applied to propargylic esters of N -protected α-amino acids ie of limited utility since only poor yields of allenic product are obtained with the N-Boc glycine esters, the system which give the most reproducible results. However, α-allenyl-α-amino

  具有烯基，乙烯基和炔属侧链的α-氨基酸可以使用基于非烯醇化物的策略合成。酯烯酸酯-克莱森重排应用于N-保护的α-氨基酸的炔丙基酯，即具有有限的用途，因为使用N-Boc甘氨酸酯仅能得到较低收率的艾伦产物，该系统提供了最可重复的结果。但是，在α-碳上完全官能化的α-烯基-α-氨基酸可通过4-烯基-2-苯基恶唑酮（通过环化和克莱森重排从N-苯甲酰基保护的氨基酸的炔丙基酯中获得）来获得。只要Meerwein试剂用于促进苯甲酰胺功能的水解。可以使用两步序列制备各种α-取代的甘氨酸盐，包括具有α-乙烯基和α-炔属功能的甘氨酸盐，包括阳离子甘氨酸合成子与各种有机镁试剂的缩合反应，然后进行水解。
• γ-Phosphono-γ-lactones. The use of allyl esters as easily removable phosphonate protecting groups
  作者：Matthias Kamber、George Just

  DOI：10.1139/v85-136

  日期：1985.4.1

  During the synthesis of γ-lactones bearing a phosphonic acid group at the γ-position, difficulties were encountered generating the free phosphonic acids from corresponding esters. A protecting group used for carboxylic acids was adapted to phosphonic acids, making this transformation easy.

  在γ-位带有膦酸基团的γ-内酯的合成过程中，遇到了从相应的酯生成游离膦酸的困难。用于羧酸的保护基团适用于膦酸，使这种转化变得容易。
• Synthesis and in vitro enzyme activity of an oxa analogue of azi-DAP
  作者：Russell J. Cox、Jeremy Durston、David I. Roper

  DOI：10.1039/b201727j

  日期：2002.4.9

  The synthesis of a novel epoxide inhibitor 6 of meso-DAP epimerase was achieved. A new and convenient assay for meso-DAP epimerase was devised which is a considerable improvement on previously reported assay methods. This assay was used to determine the inhibitory properties of 6. The epoxide 6 shows limited competitive inhibition vs. meso-DAP epimerase, but clear time dependent inhibition indicative of the expected covalent attachment at the active site. Epoxide 6, although an effective inhibitor of meso-DAP epimerase, was unstable at pH 7.3 in aqueous buffer, being hydrolysed to the corresponding diol.

  成功合成了新型环氧化物抑制剂6，用于消旋二氨基庚二酸表异构酶。设计了一种新的便捷消旋二氨基庚二酸表异构酶检测方法，相较于先前报道的检测方法有显著改进。该检测方法被用于确定抑制剂6的抑制特性。环氧化物6对消旋二氨基庚二酸表异构酶显示出有限的竞争性抑制，但存在明显的随时间递增的抑制作用，表明预期活性部位发生了共价结合。环氧化物6虽然是消旋二氨基庚二酸表异构酶的有效抑制剂，但在pH 7.3的水性缓冲液中不稳定，会水解生成对应的二醇。
• One-Step Synthesis of Strained Bicyclic Carboxylic and Boronic Amino Esters via Ruthenium-Catalysed Tandem Carbene Addition/Cyclopropanation of Enynes
  作者：Chloé Vovard-Le Bray、Hubert Klein、Pierre H. Dixneuf、Aurélie Macé、Fabienne Berrée、Bertrand Carboni、Sylvie Dérien

  DOI：10.1002/adsc.201200117

  日期：2012.7.9

  The reaction of 1,6‐ and 1,7‐enynes, derived from carboxylic and boronic amino acids, with diazo compounds in the presence of the (cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride complex [RuCl(cod)(C5Me5)] catalyst leads to the formation of strained bicyclic proline or homoproline derivatives in good yields. This catalytic transformation proceeds under mild conditions, in one step from

  在（环辛二烯）（五甲基环戊二烯）钌氯化物[RuCl（cod）（C 5 Me 5）]存在下，衍生自羧酸和硼氨基酸的1,6-和1,7-烯炔与重氮化合物的反应催化剂导致以高收率形成应变的双环脯氨酸或高脯氨酸衍生物。这种催化转化是在温和的条件下进行的，一步一步是从容易得到的炔烃开始进行的，并被应用于各种保护基团。获得了对所形成的烯基链的高立体选择性和对脯氨酸衍生物的极好的非对映选择性。