[(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester | 463952-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl [(R)-1-hydroxy-4-(4-hydroxy-phenyl)-2-methyl-but-2-yl]-carbamate；tert-butyl N-[(2R)-1-hydroxy-4-(4-hydroxyphenyl)-2-methylbutan-2-yl]carbamate
• CAS: 463952-35-4
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: XKDANMLSJTYUPV-MRXNPFEDSA-N

物化性质

• 沸点：
  476.9±45.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 {(R)-3-[4-(4-Amino-butoxy)-phenyl]-1-hydroxymethyl-1-methyl-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  NBD-labeled derivatives of the immunomodulatory drug FTY720 as tools for metabolism and mode of action studies

  摘要：

  Fluorescently labeled chiral analogs of the immunomodulatory drug FTY720 and its corresponding phosphates with variable aliphatic spacers between the aromatic ring and the NBD label have been synthesized. Determining the influence of the spacer on the in vitro phosphorylation rate by SPHK1 and 2 resulted in the identification of NBD-(R)-AAL 1c,d which are phosphorylated with an efficiency comparable to that of the unlabeled FTY720 analog (R)-AAL. Furthermore, the NBD-(R)-AAL phosphates 10c,d were proven to be a functional SIP receptor agonist. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.038
• 作为产物：
  描述：

  tert-butyl [(2R)-3-[4-(benzyloxy)phenyl]-1-(hydroxymethyl)-1-methylpropyl]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.007

文献信息

• [EN] AMINO-PROPANOL DERIVATIVES<br/>[FR] DERIVES D'AMINO-PROPANOL
  申请人：NOVARTIS AG

  公开号：WO2004024673A1

  公开（公告）日：2004-03-25

  Compounds of formula (I) wherein R1, R2, R3, R4 and R5 are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式(I)中R1、R2、R3、R4和R5的化合物，其生产过程，用途以及含有它们的药物组合物。
• [EN] AMINOPROPANOL DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTOR MODULATORS<br/>[FR] DERIVES D'AMINO-PROPANOL COMME MODULATEURS DE RECEPTEUR DE SPHINGOSINE-1-PHOSPHATE
  申请人：NOVARTIS AG

  公开号：WO2004096757A1

  公开（公告）日：2004-11-11

  Compounds of formula (I), wherein X, a, b, R1, R2, R3, R4 and R5 are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式(I)的化合物，其中X、a、b、R1、R2、R3、R4和R5如规范中定义，它们的生产过程，用途以及含有它们的药物组合物。
• [EN] AMINO ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES AMINES
  申请人：NOVARTIS AG

  公开号：WO2005085179A1

  公开（公告）日：2005-09-15

  The present invention relates to new amino acid derivatives, process for their production, their use, in particular in transplantation, and pharmaceutical compositions containing them.

  本发明涉及新的氨基酸衍生物，其生产过程，它们的用途，特别是在移植中的应用，以及含有它们的药物组合物。
• [EN] AMINO-PROPANOL DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTOR MODULATOR<br/>[FR] DERIVES D'AMINO-PROPANOL COMME MODULATEURS DE RECEPTEUR DE SPHINGOSINE-1-PHOSPHATE
  申请人：NOVARTIS AG

  公开号：WO2004096752A1

  公开（公告）日：2004-11-11

  Compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y and n are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式(I)的化合物，其中R1，R2，R3，R4，R5，R6，R7，X，Y和n的定义如说明书所述，其制备方法，其用途以及含有它们的药物组合物。
• [EN] AMINO-PROPANOL DERIVATIVES<br/>[FR] DERIVES D'AMINO-PROPANAL
  申请人：NOVARTIS AG

  公开号：WO2005118523A1

  公开（公告）日：2005-12-15

  A compound of formula (I) wherein R1, R2, R3, Ra and R5 are as defined in the specification, processes for their production, their uses, in particular in transplantation, and pharmaceutical compositions containing them.

  化合物的化学式为（I），其中R1、R2、R3、Ra和R5的定义见规范，描述了它们的制备过程，以及它们在移植等方面的应用和含有它们的药物组合物。