Tert-butyl 1-[(benzyloxy)methyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate | 193682-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: Tert-butyl 1-[(benzyloxy)methyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
• 英文别名: tert-butyl 6-hydroxy-1-(phenylmethoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 193682-78-9
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: QRRNQQRKGLTHTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl 1-[(benzyloxy)methyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 在 palladium on activated charcoal 叠氮磷酸二苯酯 、 氢气 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 41.0h， 生成 tert-butyl 1-(aminomethyl)-6-(2-methoxyethoxymethoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of a Tetradentate Oxorhenium(V) Complex Mimic of a Steroidal Estrogen

  摘要：

  We are developing oxometal(V) complexes as high affinity ligands for the estrogen receptor. When labeled with technetium-99m, these complexes might be used as imaging agents for estrogen receptor-positive breast tumors. We describe the synthesis of a tetradentate oxorhenium(V) amino amido thioether thiol (AATT) complex in which the metal complex replaces the CD ring portion of estradiol. This complex is a close steric congener of the steroid and has a similar molecular volume. It was synthesized from norphenylephrine via an efficient Pictet-Spengler cyclization to give a tetrahydroisoquinoline that was then readily elaborated into the tetradentate chelate system. Treatment with an oxorhenium(V) salt led to the formation of the desired complex as a mixture of two diastereomers in modest yield. The relative stereochemistry of these isomers was easily assigned from their NMR spectra. On the basis of their octanol-water partition coefficients, these complexes are considerably more hydrophilic than is estradiol, and their binding affinity for the estrogen receptor is low. The AATT unit in these complexes represents a new chelation system for the oxometal(V) complexes of group 7 transition metals, and compared to other closely related bisbidentate and other tetradentate systems we have studied, these complexes are quite stable. Nevertheless, the low binding affinity of these complexes for the estrogen receptor emphasizes the fact that metal complexes must most likely have an electronic complementarity with good receptor ligands, as well as a size and shape complementarity, in order for them to exhibit high affinity receptor binding.

  DOI：

  10.1021/jo970471c
• 作为产物：
  描述：

  3-羟基苯乙胺盐酸盐 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.75h， 生成 Tert-butyl 1-[(benzyloxy)methyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of a Tetradentate Oxorhenium(V) Complex Mimic of a Steroidal Estrogen

  摘要：

  We are developing oxometal(V) complexes as high affinity ligands for the estrogen receptor. When labeled with technetium-99m, these complexes might be used as imaging agents for estrogen receptor-positive breast tumors. We describe the synthesis of a tetradentate oxorhenium(V) amino amido thioether thiol (AATT) complex in which the metal complex replaces the CD ring portion of estradiol. This complex is a close steric congener of the steroid and has a similar molecular volume. It was synthesized from norphenylephrine via an efficient Pictet-Spengler cyclization to give a tetrahydroisoquinoline that was then readily elaborated into the tetradentate chelate system. Treatment with an oxorhenium(V) salt led to the formation of the desired complex as a mixture of two diastereomers in modest yield. The relative stereochemistry of these isomers was easily assigned from their NMR spectra. On the basis of their octanol-water partition coefficients, these complexes are considerably more hydrophilic than is estradiol, and their binding affinity for the estrogen receptor is low. The AATT unit in these complexes represents a new chelation system for the oxometal(V) complexes of group 7 transition metals, and compared to other closely related bisbidentate and other tetradentate systems we have studied, these complexes are quite stable. Nevertheless, the low binding affinity of these complexes for the estrogen receptor emphasizes the fact that metal complexes must most likely have an electronic complementarity with good receptor ligands, as well as a size and shape complementarity, in order for them to exhibit high affinity receptor binding.

  DOI：

  10.1021/jo970471c

文献信息

• Synthesis of a Tetradentate Oxorhenium(V) Complex Mimic of a Steroidal Estrogen
  作者：Roy K. Hom、John A. Katzenellenbogen

  DOI：10.1021/jo970471c

  日期：1997.9.1

  We are developing oxometal(V) complexes as high affinity ligands for the estrogen receptor. When labeled with technetium-99m, these complexes might be used as imaging agents for estrogen receptor-positive breast tumors. We describe the synthesis of a tetradentate oxorhenium(V) amino amido thioether thiol (AATT) complex in which the metal complex replaces the CD ring portion of estradiol. This complex is a close steric congener of the steroid and has a similar molecular volume. It was synthesized from norphenylephrine via an efficient Pictet-Spengler cyclization to give a tetrahydroisoquinoline that was then readily elaborated into the tetradentate chelate system. Treatment with an oxorhenium(V) salt led to the formation of the desired complex as a mixture of two diastereomers in modest yield. The relative stereochemistry of these isomers was easily assigned from their NMR spectra. On the basis of their octanol-water partition coefficients, these complexes are considerably more hydrophilic than is estradiol, and their binding affinity for the estrogen receptor is low. The AATT unit in these complexes represents a new chelation system for the oxometal(V) complexes of group 7 transition metals, and compared to other closely related bisbidentate and other tetradentate systems we have studied, these complexes are quite stable. Nevertheless, the low binding affinity of these complexes for the estrogen receptor emphasizes the fact that metal complexes must most likely have an electronic complementarity with good receptor ligands, as well as a size and shape complementarity, in order for them to exhibit high affinity receptor binding.