Bromo-acetic acid 2-[(1R,5R)-1-{(R)-2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-(2E)-ylidene]-ethyl ester | 207727-18-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Bromo-acetic acid 2-[(1R,5R)-1-{(R)-2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-(2E)-ylidene]-ethyl ester
• CAS: 207727-18-2
• 化学式: C₃₁H₄₉BrO₃
• 分子量: 549.632
• InChiKey: MQVYTMQCYWZJFL-DQIVUCBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Bromo-acetic acid 2-[(1R,5R)-1-{(R)-2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-(2E)-ylidene]-ethyl ester 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 以48.7%的产率得到Bromo-acetic acid 2-[(S)-2-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-ethyl ester
  参考文献：
  名称：

  Synthesis and Binding-analysis of 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D3 and 5E-25-hydroxyvitamin D3-19-methyl[(4-azido-2-nitro)phenyl]glycinate: Novel C19-modified Affinity and Photoaffinity Analogs of 25-hydroxyvitamin D3

  摘要：

  Synthesis of novel C-19-modified affinity and photoaffinity analogs of vitamin D-3 and 25-hydroxyvitamin D-3(25-OH-D-3) is described A key step in the synthesis is a Horner-Emmons reaction between C-19-nor-cyclovitamin D-3-C-19-ketone or C-19-nor-25-hydroxy-cyclovitamin D-3-C-19-ketone and diethyl cyanomethylphosphonate. Competitive radioligand binding assays with human serum vitamin D-binding protein (DBP) and 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D-3 and 5E-25-hydroxyvitamin in D-3-19-methyl[4-azido-2-nitro)phenyl]glycinate, 25-OH-D-3-analogs containing affinity and photoaffinity probes at C-19-position, demonstrated that these compounds displaced radiolabeled 25-OH-D-3 from the binding pocket of DBP in it dose-dependent manner. Thus, these affinity and photoaffinity analogs are potentially useful in determining the ligand binding site topographies of DBP and possibly the vitamin D receptor. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00009-9
• 作为产物：
  描述：

  [(1R,5R)-1-{(R)-2-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-(2E)-ylidene]-acetaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 Bromo-acetic acid 2-[(1R,5R)-1-{(R)-2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-(2E)-ylidene]-ethyl ester
  参考文献：
  名称：

  Synthesis and Binding-analysis of 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D3 and 5E-25-hydroxyvitamin D3-19-methyl[(4-azido-2-nitro)phenyl]glycinate: Novel C19-modified Affinity and Photoaffinity Analogs of 25-hydroxyvitamin D3

  摘要：

  Synthesis of novel C-19-modified affinity and photoaffinity analogs of vitamin D-3 and 25-hydroxyvitamin D-3(25-OH-D-3) is described A key step in the synthesis is a Horner-Emmons reaction between C-19-nor-cyclovitamin D-3-C-19-ketone or C-19-nor-25-hydroxy-cyclovitamin D-3-C-19-ketone and diethyl cyanomethylphosphonate. Competitive radioligand binding assays with human serum vitamin D-binding protein (DBP) and 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D-3 and 5E-25-hydroxyvitamin in D-3-19-methyl[4-azido-2-nitro)phenyl]glycinate, 25-OH-D-3-analogs containing affinity and photoaffinity probes at C-19-position, demonstrated that these compounds displaced radiolabeled 25-OH-D-3 from the binding pocket of DBP in it dose-dependent manner. Thus, these affinity and photoaffinity analogs are potentially useful in determining the ligand binding site topographies of DBP and possibly the vitamin D receptor. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00009-9