methyl <2-²H₂>glycinate hydrochloride | 88291-62-7

• 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 <2-²H₂>glycinate hydrochloride
• 英文别名: <2-2H2>glycine methyl ester hydrochloride；methyl glycinate-2,2-d₂ hydrochloride；Methyl 2-amino-2,2-dideuterioacetate;hydrochloride
• CAS: 88291-62-7
• 化学式: C₃H₇NO₂*ClH
• 分子量: 127.539
• InChiKey: COQRGFWWJBEXRC-IYPYQTRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl <2-²H₂>glycinate hydrochloride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以57%的产率得到2-amino(2,2-²H₂)ethan-1-ol
  参考文献：
  名称：

  Tilley, Kevin; Akhtar, Mahmoud; Gani, David, Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3079 - 3088

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl bis(methylsulfanyl)methylene<2,2-(2)H2>glycinate 在 盐酸 作用下， 生成 methyl <2-²H₂>glycinate hydrochloride
  参考文献：
  名称：

  Synthesis of enantiopure α-deuteriated Boc-L-amino acids

  摘要：

  An alternative scheme for the synthesis of enantiopure alpha-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene [2,2-H-2(2)] glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated alpha-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-H-2]-Ala, -Leu,-Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis, Boc-[2,2-H-2(2)]Gly was also prepared.

  DOI：

  10.1039/p19960000537

文献信息

• DEUTERATED BENZIMIDAZOLE COMPOUND AND MEDICAL USE THEREOF
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：US20200017450A1

  公开（公告）日：2020-01-16

  The present invention relates to a medicament for treating or preventing a disease involving Na channel, for example, neuropathic pain, nociceptive pain, inflammatory pain, small-fiber neuropathy, erythromelalgia, paroxysmal extreme pain disorder, dysuria, or multiple sclerosis, comprising a compound of formula (I) wherein R 1a , R 1b , R 1c , and R 1d are hydrogen, halogen, cyano, C 1-4 alkyl, C 1-4 alkoxy, etc., provided that at least one of R 1a , R 1b , R 1c and R 1d is the above C 6-10 aryl, C 6-10 aryloxy, etc., R 2 and R 3 are hydrogen, C 1-6 alkyl, C 3-10 cycloalkyl, etc., R 4 is hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, etc., m is 0, 1, or 2, L is CR 7 R 8 , R 7 and R 8 are hydrogen, hydroxy group, C 1-4 alkyl, C 1-4 alkoxy, etc., or a pharmaceutically acceptable salt thereof.

  该发明涉及一种用于治疗或预防涉及Na通道的疾病的药物，例如神经痛、伤害性疼痛、炎症性疼痛、小纤维神经病、红细胞增多症、阵发性极端疼痛障碍、排尿困难或多发性硬化等，包括式(I)的化合物，其中R1a、R1b、R1c和R1d为氢、卤素、氰基、C1-4烷基、C1-4烷氧基等，但至少其中一个为上述的C6-10芳基、C6-10芳氧基等，R2和R3为氢、C1-6烷基、C3-10环烷基等，R4为氢、C1-6烷基、C3-7环烷基等，m为0、1或2，L为CR7R8，R7和R8为氢、羟基、C1-4烷基、C1-4烷氧基等，或其药学上可接受的盐。
• Hydrogen‐Borrowing Alkylation of 1,2‐Amino Alcohols in the Synthesis of Enantioenriched γ‐Aminobutyric Acids
  作者：Christopher J. J. Hall、William R. F. Goundry、Timothy J. Donohoe

  DOI：10.1002/anie.202100922

  日期：2021.3.22

  For the first time we have been able to employ enantiopure 1,2‐amino alcohols derived from abundant amino acids in C−C bond‐forming hydrogen‐borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub‐stoichiometric base and protection of the nitrogen with a sterically

  我们首次能够在 C-C 键形成借氢烷基化反应中使用源自丰富氨基酸的对映体纯 1,2-氨基醇。使用芳基酮 Ph*COMe 可以促进这些反应。通过使用亚化学计量的碱并用位阻三苯甲烷（三苯甲基）或苄基保护氮，可以防止烷基化过程中胺立构中心的外消旋化。 Ph* 和三苯甲基在一锅中即可轻松裂解，得到 γ-氨基丁酸 (GABA) 盐酸盐产品，无需进一步纯化。这两个步骤可以依次进行，无需分离借氢中间体，从而无需柱色谱法。
• [EN] ISOTOPICALLY LABELED BILE ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE BILIAIRE À MARQUAGE ISOTOPIQUE
  申请人：INTERCEPT PHARMACEUTICALS INC

  公开号：WO2019023103A1

  公开（公告）日：2019-01-31

  The present application relates to isotopically labeled compounds of Formula I and methods of preparation and use thereof.

  本申请涉及公式I的同位素标记化合物的制备和使用方法。
• Copper(I)‐Catalyzed Asymmetric Allylation of Ketones with 2‐Aza‐1,4‐Dienes
  作者：Zhi‐Zhou Pan、Jia‐Heng Li、Hu Tian、Liang Yin

  DOI：10.1002/anie.202315293

  日期：2024.1.2

  A copper(I)-catalyzed asymmetric allylation of ketones with 2-aza-1,4-dienes (N-allyl-1,1-diphenylmethanimines) is disclosed, which affords a series of functionalized homoallyl tertiary alcohols in high to excellent enantioselectivity.

  公开了铜(I)催化的酮与2-氮杂-1,4-二烯( N-烯丙基-1,1-二苯基甲胺)的不对称烯丙基化，其提供了一系列具有高至优异对映选择性的官能化高烯丙基叔醇。
• Herbert, Richard B.; Knaggs, Andrew R., Journal of the Chemical Society. Perkin transactions I, 1992, # 1, p. 109 - 114
  作者：Herbert, Richard B.、Knaggs, Andrew R.

  DOI：——

  日期：——