(S)-(Z)-[2-(5-hydroxy-2-methylene-cyclohexylidene)ethyl]di-phenylphosphineoxide | 1236132-10-7

• 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: (S)-(Z)-[2-(5-hydroxy-2-methylene-cyclohexylidene)ethyl]di-phenylphosphineoxide
• 英文别名: (S)-(Z)-(2-(5-hydroxy-2-methylenecyclohexylidene)ethyl)diphenylphosphine oxide；(S)-(Z)-[2-(5-hydroxy-2-methylenecyclohexylidene)ethyl]diphenylphosphine oxide；(1S,3Z)-3-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexan-1-ol
• CAS: 1236132-10-7
• 化学式: C₂₁H₂₃O₂P
• 分子量: 338.386
• InChiKey: HDCWPIOUGUKXOF-BSKAQADGSA-N

物化性质

• 沸点：
  485.9±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(Z)-[2-(5-hydroxy-2-methylene-cyclohexylidene)ethyl]di-phenylphosphineoxide 在 咪唑 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 23-oxa-25,26-dehydrovitamin D3
  参考文献：
  名称：

  Studies on vitamin D (calciferol) and its analogs. 25. Studies on a convergent route to side-chain analogues of vitamin D: 25-hydroxy-23-oxavitamin D3

  摘要：

  DOI：

  10.1021/jo00157a004
• 作为产物：
  描述：

  <(1Z),(5S)>-2-<5-hydroxy-2-methylcyclohexylidene>-ethanol 在 甲醇 、 sodium hydroxide 、 (氯亚甲基)二甲基氯化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-(Z)-[2-(5-hydroxy-2-methylene-cyclohexylidene)ethyl]di-phenylphosphineoxide
  参考文献：
  名称：

  Lythgoe,B. et al., Journal of the Chemical Society. Perkin transactions I, 1978, p. 590 - 595

  摘要：

  DOI：

文献信息

• Synthesis of C-11 linked active ester derivatives of vitamin D3 and their conjugations to 42-residue helix–loop–helix peptides
  作者：Qi Zhang、Thomas Norberg、Jonas Bergquist、Lars Baltzer

  DOI：10.1016/j.tet.2010.04.051

  日期：2010.6

  Derivatives of vitamin D3 carrying an 8-carbon linker at C-11 terminating in an active ester were synthesized from commercial vitamin D3 using a disassembly–reassembly strategy. Vitamin D3 was cleaved at the C6–C7 double bond and the ‘upper’ fragment was converted, via a series of reactions, to derivatives substituted at C-11 with an 8-carbon linker terminating in an ethyl ester. Reassembly with modified

  维生素D 3的衍生物在C-11端带有8个碳的连接基，并终止于活性酯中，是使用分解-重组策略从商业维生素D 3合成的。维生素D 3在C6-C7双键处裂解，“上部”片段通过一系列反应转化为在C-11处被8碳连接基取代的衍生物，该连接基终止于乙酯。使用Horner-Wittig烯烃化反应将修饰的“低级”片段重新组装，然后进行连接基酯水解，并用对硝基苯酚进行再酯化，得到C-11取代的对硝基苯酯。这些维生素D衍生物通过它们的p反应与42个氨基酸的螺旋-环-螺旋肽缀合肽上带有赖氨酰基侧链氨基的-硝基苯基酯。维生素D-肽结合物是维生素D-结合蛋白的潜在特异性结合物候选物，通过质谱和CD测量表征。
• Synthesis of vitamin D3 analogues with A-ring modifications to directly measure vitamin D levels in biological samples
  作者：Alba Hernández-Martín、Tania González-García、Margaret Lawlor、Lesley Preston、Vicente Gotor、Susana Fernández、Miguel Ferrero

  DOI：10.1016/j.bmc.2013.10.013

  日期：2013.12

  C-3-substituted 25-hydroxyvitamin D-3 analogues were synthesized as tools to directly measure levels of vitamin D in biological samples. The strategy involves vinyloxycarbonylation of the 3 beta-hydroxy group and formation of a carbamate bond with a hydroxyl or amino group at the end of the alkyl chain. Biotinylated conjugates of synthesized derivatives were generated to be linked with vitamin D binding protein (DBP). The spacer group present in the alkyl chain is important in the binding of antibodies to the analogue-DBP complex. When compared to 25-hydroxyvitamin D-3-DBP, the binding of some antibodies to the analogue-DBP complex of the 25-hydroxyvitamin D-3 derivative 10 that posses an 8-aminoctyl alkyl chain is significantly reduced, but this analogue displaced [26,27-H-3]-25-hydroxyvitamin D-3 from DBP. In contrast, the 8-hydroxyoctyl alkyl chain analogue 9 showed less displacement. (C) 2013 Elsevier Ltd. All rights reserved.