(S)-3-[4-Benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester | 364041-50-9

• 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: (S)-3-[4-Benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-(1,3-dioxoisoindol-2-yl)-3-[4-phenylmethoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate
• CAS: 364041-50-9
• 化学式: C₃₁H₃₂BNO₇
• 分子量: 541.409
• InChiKey: BYMAQKXBDYPVBD-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-[4-Benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester 在 盐酸 、 二乙醇胺 作用下， 生成 [5-[(2S)-2-(1,3-dioxoisoindol-2-yl)-3-methoxy-3-oxopropyl]-2-phenylmethoxyphenyl]boronic acid
  参考文献：
  名称：

  Synthesis of the biaryl moiety of the proteasome inhibitors TMC-95 via a ligandless Pd(OAc)2-catalyzed Suzuki-coupling reaction

  摘要：

  The biaryl moiety of proteasome inhibitors TMC-95 was synthesized via a Pd(OAc)(2)-catalyzed Suzuki-coupling reaction of 7-iodoisatin and a tyrosine-derived arylboronic acid in the absence of phosphine ligands using potassium fluoride as a base. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00966-2
• 作为产物：
  描述：

  N-Phthaloyl-L-tyrosin 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 TEA 、 碘 、 silver trifluoroacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-[4-Benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of the biaryl moiety of the proteasome inhibitors TMC-95 via a ligandless Pd(OAc)2-catalyzed Suzuki-coupling reaction

  摘要：

  The biaryl moiety of proteasome inhibitors TMC-95 was synthesized via a Pd(OAc)(2)-catalyzed Suzuki-coupling reaction of 7-iodoisatin and a tyrosine-derived arylboronic acid in the absence of phosphine ligands using potassium fluoride as a base. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00966-2

文献信息

• Synthesis of the biaryl moiety of the proteasome inhibitors TMC-95 via a ligandless Pd(OAc)2-catalyzed Suzuki-coupling reaction
  作者：Dawei Ma、Qingquan Wu

  DOI：10.1016/s0040-4039(01)00966-2

  日期：2001.7

  The biaryl moiety of proteasome inhibitors TMC-95 was synthesized via a Pd(OAc)(2)-catalyzed Suzuki-coupling reaction of 7-iodoisatin and a tyrosine-derived arylboronic acid in the absence of phosphine ligands using potassium fluoride as a base. (C) 2001 Elsevier Science Ltd. All rights reserved.