(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene | 122172-46-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene
• 英文别名: (3S,5R)-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene；(1R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-ethynyl-4-methylcyclohex-3-en-1-ol
• CAS: 122172-46-7
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: RFSMRNNKLKAWHP-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (3S,5S)-3-[(tert-butyldimethylsilyl)oxy]-1-ehtynyl-5-hydroxy-2-methylcyclohex-1-ene
  参考文献：
  名称：

  Efficient Synthesis of Novel 1α-Amino and 3β-Amino Analogues of 1α,25-Dihydroxyvitamin D₃

  摘要：

  Convenient synthetic routes to 1alpha-amino-25-hydroxyvitamin D-3 (3) and 3beta-amino-3-deoxy-1alpha,25-dihy-droxyvitamin D-3 (4), novel analogues of vitamin D-3 bearing an amino group at the C-1 or C-3 position, have been developed starting from (S)-(+)-carvone. Construction of the A-ring fragments was accomplished by selective enzymatic hydrolysis of a diester intermediate and introduction of the amino group under Mitsunobu conditions.

  DOI：

  10.1021/jo026474t
• 作为产物：
  描述：

  (3S,5R)-5-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到(3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene
  参考文献：
  名称：

  Efficient Synthesis of Novel 1α-Amino and 3β-Amino Analogues of 1α,25-Dihydroxyvitamin D₃

  摘要：

  Convenient synthetic routes to 1alpha-amino-25-hydroxyvitamin D-3 (3) and 3beta-amino-3-deoxy-1alpha,25-dihy-droxyvitamin D-3 (4), novel analogues of vitamin D-3 bearing an amino group at the C-1 or C-3 position, have been developed starting from (S)-(+)-carvone. Construction of the A-ring fragments was accomplished by selective enzymatic hydrolysis of a diester intermediate and introduction of the amino group under Mitsunobu conditions.

  DOI：

  10.1021/jo026474t

文献信息

• Novel A-ring homodimeric C-3-carbamate analogues of 1α,25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation
  作者：Daniel Oves、Susana Fernández、Lieve Verlinden、Roger Bouillon、Annemieke Verstuyf、Miguel Ferrero、Vicente Gotor

  DOI：10.1016/j.bmc.2006.07.021

  日期：2006.11

  The synthesis of a new class of vitamin D-3 analogues in which two units of 1 alpha,25-dihydroxyvitamin D-3 are linked at the C-3 position by a dicarbamate functionality of variable length is described. The analogues demonstrated no affinity for the vitamin D receptor and possessed no antiproliferative or transactivating properties. (c) 2006 Elsevier Ltd. All rights reserved.
• Studies of vitamin D (calciferol) and its analogs. 35. Synthesis and biological activity of 9,11-dehydrovitamin D3 analogs: stereoselective preparation of 6.beta.-vitamin D vinylallenes and a concise enynol synthesis for preparing the A-ring
  作者：William H. Okamura、J. Miguel Aurrecoechea、Richard A. Gibbs、Anthony W. Norman

  DOI：10.1021/jo00278a018

  日期：1989.8