((R)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-phosphinic acid | 131829-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((R)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-phosphinic acid
• 英文别名: [(1R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]phosphinic acid
• CAS: 131829-52-2
• 化学式: C₁₃H₂₀NO₄P
• 分子量: 285.28
• InChiKey: USFQDGCRSQFUQZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((R)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-phosphinic acid 、 2-溴甲基丙烯酸乙酯 在 三甲基氯硅烷 、 三乙基硼 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 {(R)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}[2-(ethoxycarbonyl)-4-methylpentyl]phosphinic acid
  参考文献：
  名称：

  Late-Stage Diversification of Phosphinic Dehydroalanine Pseudopeptides Based on a Giese-Type Radical C-Alkylation Strategy

  摘要：

  A straightforward, late-stage diversification strategy for the installation of side chains on readily accessible unsaturated phosphinopeptidic scaffolds based on a Giese-type addition of alkyl radicals has been investigated. Among different alternatives, the preferred methodology is operationally simple as it can be carried out in an open flask with no need for protection of acidic moieties. Direct application to the synthesis of SPPS-compatible building blocks or to longer peptides is also reported.

  DOI：

  10.1021/acs.orglett.9b00857
• 作为产物：
  描述：

  (1-(N-(tert-butyloxycarbonyl)amino)-2-phenylethyl) phosphinic acid 以39%的产率得到
  参考文献：
  名称：

  SAMPSON, NICOLE S.;BARTLETT, PAUL A., BIOCHEMISTRY, 30,(1991) N, C. 2255-2263

  摘要：

  DOI：

文献信息

• Phosphinic acids
  申请人：Hilpert Hans

  公开号：US20050107341A1

  公开（公告）日：2005-05-19

  The present invention relates to phosphinic acid derivatives of formula I wherein R 1 , R 2 , R 3 and R 4 are described hereinabove. These compounds can be used in the treatment or prevention of a disease related to the inhibition of β-secretase, inter alia for the treatment of Alzheimer's disease.

  本发明涉及式I的膦酸衍生物，其中R1、R2、R3和R4如上所述。这些化合物可用于治疗或预防与β-分泌酶抑制有关的疾病，包括治疗阿尔茨海默病。
• Diastereoselective Synthesis of Phosphinic Dipeptide Isosteres: Domino Chirality Transfer during a Stereocontrolled P-Michael Reaction
  作者：Angelos Lelis、Nikolaos Skoulikas、Mirto Papathanasopoulou、Kostas Voreakos、Dimitris Georgiadis

  DOI：10.1021/acs.orglett.3c02335

  日期：2023.9.15

  A highly diastereoselective P-Michael addition of chiral aminophosphinic acids to achiral acrylates has been developed, leading to phosphinic dipeptide isosteres in high yields and dr of up to >50:1. The method allows for the diastereoselective preparation of target compounds without the need for chiral auxiliaries or P-chiral substrates. A possible mechanistic explanation involves a domino chirality

  已开发出手性氨基次膦酸与非手性丙烯酸酯的高度非对映选择性 P-Michael 加成反应，可产生高产率的次膦二肽电子等排体，dr 高达 >50:1。该方法允许非对映选择性制备目标化合物，而不需要手性助剂或 P-手性底物。一种可能的机制解释涉及从氨基次膦酸到 P 中心的多米诺骨牌手性转移，通过关键的二苯甲基酯基团放大，然后转移到 α-碳。
• PHOSPHINIC ACID DERIVATIVES, BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1685142A1

  公开（公告）日：2006-08-02
• US7345082B2
  申请人：——

  公开号：US7345082B2

  公开（公告）日：2008-03-18
• [EN] PHOSPHINIC ACIDS DERIVATIVES, BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] DERIVES D'ACIDE PHOSPHINIQUE, INHIBITEURS DE LA BETA-SECRETASE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005044830A1

  公开（公告）日：2005-05-19

  The present invention relates to phosphinic acid derivatives of formula (I) wherein R1 is aryl or heteroaryl, R2 is (C1-C5)-alkyl or phenyl, R3 is hydrogen, (C1-C5)-alky, O-(C1-C5)-alkyl or phenyl, R4 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, phenyl, pyridyl or indolyl, and pharmaceutically acceptable salts thereof. The compounds can be used in the treatment or prevention of a disease related to the inhibition of beta-secretase, inter alia for the treatment of Alzheimer’s disease.