N-(Benzyloxycarbonyl)valine methyl ester | 134306-34-6

• 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-(Benzyloxycarbonyl)valine methyl ester
• 英文别名: N-Z-Val-OMe；N-benzyloxycarbonyl-DL-valine methyl ester；N-Benzyloxycarbonyl-DL-valin-methylester；N-(Benzyloxycarbonyl)-valine methyl ester；methyl 3-methyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 134306-34-6
• 化学式: C₁₄H₁₉NO₄
• mdl: MFCD12487658
• 分子量: 265.309
• InChiKey: LKTVCURTNIUHBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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-(Benzyloxycarbonyl)valine methyl ester 在 盐酸 、 甲醇 、 palladium on activated charcoal 、 乙醇 作用下， 生成 (+-)-DL-valine-(trans-2-hydroxy-cyclohexylamide)
  参考文献：
  名称：

  �ber ?-Aminos�ure-2-hydroxy-cyclohexylamide

  摘要：

  AbstractCis‐ and trans‐2‐hydroxycyclohexylamides of α‐aminoacids, a new class of potential tridentate chelating agents, have been synthesized. The complexing properties of several of these compounds have been investigated.

  DOI：

  10.1002/hlca.19590420523
• 作为产物：
  描述：

  N-(t-Butyldimethylsilyloxycarbonyl)-valine methyl ester 生成 N-(Benzyloxycarbonyl)valine methyl ester
  参考文献：
  名称：

  OFUNA, YASUSI;SAKAIYA, MASAXIRO

  摘要：

  DOI：

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。
• Stereoselective synthesis of allylic amines by rearrangement of allylic trifluoroacetimidates: stereoselective synthesis of polyoxamic acid and derivatives of other α-amino acids
  作者：Ian Savage、Eric J. Thomas、Peter D. Wilson

  DOI：10.1039/a905772b

  日期：——

  On heating in xylene under reflux, allylic trifluoroacetimidates undergo [3,3] sigmatropic rearrangement to regioisomeric allylic trifluoroacetamides. Examples include the rearrangements of the trifluoroacetimidates 16 and 73 to the trifluoroacetamides 17 and 74, which were incorporated into stereoselective syntheses of polyoxamic acid 1, and the rearrangement of the trifluoroacetimidate 26. The rearrangement was the key step in asymmetric syntheses of the (S)- and (R)-valine derivatives 37 and 48. Other examples include rearrangements of the trifluoroacetimidates 52, 54 and 56 prepared from geraniol, cinnamyl alcohol and sorbyl alcohol, respectively, and the more complex trifluoroacetimidates 62 and 69. The stereoselectivity of these rearrangements, which are somewhat faster than rearrangements of analogous allylic trichloroacetimidates, is consistent with the participation of chair-like, six-membered, transition structures.

  在甲苯中回流加热时，烯丙基三氟乙亚胺酸酯会发生[3,3] σ迁移重排，生成区域异构的烯丙基三氟乙酰胺。例如，三氟乙亚胺酸酯16和73重排生成三氟乙酰胺17和74，这些被用于合成聚氧基酸1的选择性合成中，以及三氟乙亚胺酸酯26的重排。这一重排是对映选择性合成(S)-和(R)-缬氨酸类似物37和48的关键步骤。其他例子包括由香叶醇、肉桂醇和苏儿醇分别制备的三氟乙亚胺酸酯52、54和56的重排，以及更复杂的三氟乙亚胺酸酯62和69的重排。这些重排的立体选择性比类似的烯丙基三氯乙亚胺酸酯重排稍快，与椅式六元过渡态结构的参与相符。
• A Synthesis of a New Type of Alkoxycarbonylating Reagents from 1,1-Bis[6-(trifluoromethyl)benzotriazolyl] Carbonate (BTBC) and Their Reactions
  作者：Kazuyoshi Takeda、Kanoko Tsuboyama、Mitsuho Hoshino、Miyuki Kishino、Haruo Ogura

  DOI：10.1055/s-1987-28002

  日期：——

  1,1′-Bis[6-(trifluoromethyl])benzotriazolyl] carbonate (BTBC) was prepared from 1-hydroxy-6-trifluoromethylbenzotriazole and trichloromethyl chloroformate (trichloromethyl carbonochloridate). The reaclion of BTBC and alcohols afforded the corresponding active carbonates which were converted into the corresponding carbamates and carbonates.

  1,1′-双[6-(三氟甲基)苯并三唑基]碳酸酯（BTBC）是由1-羟基-6-三氟甲基苯并三唑和三氯甲基氯甲酸酯（三氯甲基碳酸氯化物）合成的。BTBC与醇的反应生成相应的活性碳酸酯，这些碳酸酯进一步转化为相应的氨基甲酸酯和碳酸酯。
• Synthesis and SAR Studies of diarylpyrrole anticoccidial agents
  作者：Xiaoxia Qian、Gui-Bai Liang、Dennis Feng、Michael Fisher、Tami Crumley、Sandra Rattray、Paula M. Dulski、Anne Gurnett、Penny Sue Leavitt、Paul A. Liberator、Andrew S. Misura、Samantha Samaras、Tamas Tamas、Dennis M. Schmatz、Matthew Wyvratt、Tesfaye Biftu

  DOI：10.1016/j.bmcl.2006.01.041

  日期：2006.5

  pyrroles were prepared and evaluated as anticoccidial agents in both in vitro and in vivo assays. Among the compounds evaluated, the dimethylamine-substituted pyrrole 19a is the most potent inhibitor of Eimeria tenella PKG (cGMP-dependent protein kinase). Further SAR studies on the side chain of the 2-pyrrolidine nitrogen did not enhance in vivo anticoccidial activity.

  制备了2-（4-氟苯基）-3-（4-吡啶基）-5-取代的吡咯，并在体外和体内试验中将其作为抗球虫药进行了评估。在所评估的化合物中，二甲胺取代的吡咯19a是Eimeria tenella PKG（依赖cGMP的蛋白激酶）的最有效抑制剂。对2-吡咯烷氮侧链的进一步SAR研究并未增强体内抗球虫活性。
• One-pot conversion of N-benzyloxycarbonyl group into N-tert-butoxycarbonyl group
  作者：Masahiro Sakaitani、Keiko Hori、Yasufumi Ohfune

  DOI：10.1016/0040-4039(88)85064-0

  日期：1988.1

  An efficient one-pot two stage transformation of the N-Z group into the N-t-Boc group was carried out under the neutral conditions.

  在中性条件下进行了NZ组向N- t- Boc组的有效的一锅两阶段转化。