methyl N,N-dibenzyl-L-leucinate | 189562-54-7

• 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: methyl N,N-dibenzyl-L-leucinate
• 英文别名: methyl (2S)-2-(dibenzylamino)-4-methylpentanoate
• CAS: 189562-54-7
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: LWAGDNNNPYPMLM-FQEVSTJZSA-N

物化性质

• 沸点：
  409.5±33.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N,N-dibenzyl-L-leucinate 在 titanium(IV) isopropylate 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-((S)-1-Amino-3-methyl-butyl)-cyclopropanol
  参考文献：
  名称：

  环丙醇与 1,2,3-三唑开环偶联合成稠合三唑

  摘要：

  已经实现了环丙醇与1,2,3-三唑的自由基开环芳基化。该合成方案可以直接从容易获得的手性环丙醇中高效地获得各种结构多样的手性 4,5,6,7-四氢[1,2,3]三唑并[1,5- a ]吡啶。

  DOI：

  10.1021/acs.orglett.4c00702
• 作为产物：
  描述：

  L-亮氨酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 生成 methyl N,N-dibenzyl-L-leucinate
  参考文献：
  名称：

  环丙醇与 1,2,3-三唑开环偶联合成稠合三唑

  摘要：

  已经实现了环丙醇与1,2,3-三唑的自由基开环芳基化。该合成方案可以直接从容易获得的手性环丙醇中高效地获得各种结构多样的手性 4,5,6,7-四氢[1,2,3]三唑并[1,5- a ]吡啶。

  DOI：

  10.1021/acs.orglett.4c00702

文献信息

• N-Benzyl-Protection of Amino Acid Derivatives by Reductive Alkylation with α-Picoline-Borane
  作者：Tsutomu Yokomatsu、Yasushi Kawase、Takehiro Yamagishi、Teruo Kutsuma、Tadashi Kataoka、Kimio Ueda、Takeo Iwakuma、Tadashi Nakata

  DOI：10.1055/s-0029-1218707

  日期：2010.5

  derivatives with a benzyl group by reductive alkylation of amino acid derivatives with α-picoline-borane is described. Amino acid esters or amino alcohols were treated with aryl aldehydes in methanol/acetic­ acid in the presence of α-picoline-borane to give N-benzyl-protected amino acid derivatives in good yields. amino acid esters - amino alcohols - benzylation - protecting groups - reductions

  描述了一种方便的方法，该方法通过用α-甲基吡啶-硼烷对氨基酸衍生物进行还原性烷基化来用苄基对氨基酸衍生物进行N-保护。在α-甲基吡啶硼烷的存在下，用芳基醛在甲醇/乙酸中处理氨基酸酯或氨基醇，以高收率得到N-苄基保护的氨基酸衍生物。 氨基酸酯-氨基醇-苄基化-保护基-还原
• Organic Compounds
  申请人：Ehara Takeru

  公开号：US20090192148A1

  公开（公告）日：2009-07-30

  The invention relates to 3,5-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-substituted piperidine compound, and/or a method of treatment comprising administering a 3,5-substituted piperidine compound, a method for the manufacture of a 3,5-substituted piperidine compound, and novel intermediates and partial steps for its synthesis. The compounds have the formula I′ wherein R1, R2, T, R3 and R4 areas defined in the specification.

  本发明涉及3,5-取代哌啶化合物，这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病（=失调）；该类化合物用于制备治疗依赖肾素活性疾病的制剂；该类化合物用于治疗依赖肾素活性的疾病；包括3,5-取代哌啶化合物的制药配方和/或包括给予3,5-取代哌啶化合物的治疗方法，以及制造3,5-取代哌啶化合物的新型中间体和部分合成步骤。该化合物的式子为I'，其中R1、R2、T、R3和R4在规范中有定义。
• Alpha-hydroxy-beta-aminothiolcarboxylic esters and method and intermediates for their production
  申请人：Ajinomoto Co., Inc.

  公开号：EP0767168A2

  公开（公告）日：1997-04-09

  A method for producing α-hydroxy-β-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from α-amino acids. Starting from an N-protected α-amino acid ester, this is converted into a β-ketosulfoxide, which is then reacted with an acid to give an α-keto-hemimercaptal. This is acylated and then processed with a base to obtain an N-protected α-acyloxy-β-amino-thioester, which is then saponified to obtain the intended compound.

  一种用α-氨基酸生产α-羟基-β-氨基羧酸衍生物的方法，这种衍生物是生产各种艾滋病毒蛋白酶抑制剂、肾素抑制剂和致癌物质的中间体。 从 N 保护的 α-氨基酸酯开始，将其转化为 β-酮亚砜，然后与酸反应生成 α-酮半巯基。将其酰化，然后用碱处理，得到 N-保护的 α-乙酰氧基-β-氨基硫代酯，然后将其皂化，得到预期的化合物。
• 3 , 5-substitued piperidine compounds as renin inhibitors
  申请人：Novartis AG

  公开号：EP2420491A1

  公开（公告）日：2012-02-22

  The invention relates to 3,5-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (= disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-substituted piperidine compound, and/or a method of treatment comprising administering a 3,5-substituted piperidine compound, a method for the manufacture of a 3, 5-substituted piperidine compound, and novel intermediates and partial steps for its synthesis. The compounds (which can also be present as salts) have the formula I' wherein R1, R2, T, R3, R4, R7 and R8 are as defined in the specification and R6 is OH.

  本发明涉及3,5-取代的哌啶化合物，这些化合物用于温血动物的诊断和治疗，特别是用于治疗依赖于肾素活性的疾病（=紊乱）；使用该类化合物制备药物制剂，用于治疗依赖于肾素活性的疾病；该类化合物在治疗依赖于肾素活性的疾病中的用途；包含 3,5-取代的哌啶化合物的药物制剂，和/或包括施用 3,5-取代的哌啶化合物的治疗方法，3,5-取代的哌啶化合物的制造方法，及其合成的新型中间体和部分步骤。 这些化合物（也可以以盐的形式存在）具有式 I' 其中 R1、R2、T、R3、R4、R7 和 R8 如说明书中所定义，R6 为 OH。
• Stereoselective total synthesis of amicoumacin C
  作者：Tomomi Suzuki、Tomohiro Nagasawa、Masaru Enomoto、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2015.02.014

  日期：2015.4

  The enantio- and diastereoselective total synthesis of amicoumacin C was achieved from L-phenylalanine in 17% overall yield through 13 steps via condensation between an amine and an acid segment. The amine segment was prepared from L-leucine in 42% yield by a 7-step sequence involving a diastereoselective reduction of an alpha-dibenzylamino ketone intermediate, while the acid segment was obtained from L-phenylalanine by using acidic hydrolysis of an acetonide-protected amide accompanied by concomitant lactonization as a key step. (C) 2015 Elsevier Ltd. All rights reserved.