cis,cis-3-hydroxy-5-methyl-carbonyloxy-cyclohexyl acetate | 171866-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis,cis-3-hydroxy-5-methyl-carbonyloxy-cyclohexyl acetate
• 英文别名: cis-1,3-diacetoxy-5-hydroxy-cyclohexane
• CAS: 171866-13-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: RSGVAVNCTCYOOK-ILWJIGKKSA-N

物化性质

• 沸点：
  285.3±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis,cis-3-hydroxy-5-methyl-carbonyloxy-cyclohexyl acetate 在 4-二甲氨基吡啶 porcine liver esterase 、 氟化氢吡啶 、 三乙胺 作用下， 以 phosphate buffer 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 90.0h， 生成 [(1R,3S)-3-hydroxy-5-oxocyclohexyl] acetate
  参考文献：
  名称：

  Total Syntheses of 2,2‘-epi-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin

  摘要：

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.

  DOI：

  10.1021/ja0685708
• 作为产物：
  描述：

  cis,cis-3,5-di(methylcarbonyloxy)cyclohexyl acetate 在 porcine liver esterase 、 sodium phosphate buffer 作用下， 反应 12.0h， 以90%的产率得到cis,cis-3-hydroxy-5-methyl-carbonyloxy-cyclohexyl acetate
  参考文献：
  名称：

  Simple, Efficient Chemoenzymatic Synthesis of (S)-5-(tert-Butyldimethylsilyloxy)-2-cyclohexenone and Enantiomeric Ketone Intermediates of 19-Nor-1α,25-dihydroxyvitamin D₃

  摘要：

  DOI：

  10.1021/jo016141g

文献信息

• A Novel Synthesis of 19-Nor 1α,25-dihydroxyvitamin D3 and Related Analogues
  作者：Pei-qiang Huang、Katrien Sabbe、Mieke Pottie、Maurits Vandewalle

  DOI：10.1016/0040-4039(95)01730-6

  日期：1995.11

  19-Nor-1 α,25-dihydroxyvitamin D3 (2) was synthesized from A-ring precursor 5 and ketone 4. Two synthesis of 5 were studied; one starting from (-)-quinic acid as a template and one starting from cis-1,3,5-cyclohexanetriol via a chemoenzymatic approach.

  由A环前体5和酮4合成19-Nor-1α，25-dihydroxyvitamin D 3（2）。研究了5的两个合成；一种通过化学酶促方法以（-）-奎尼酸为模板，另一种以顺式1,3,5-环己三醇为模板。
• Multiselective enzymatic reactions for the synthesis of protected homochiral cis- and trans-1,3,5-cyclohexanetriols
  作者：Beat Wirz、Hans Iding、Hans Hilpert

  DOI：10.1016/s0957-4166(00)00368-2

  日期：2000.10

  For the synthesis of the potentially antipsoriatric vitamin D derivative 3 (Ro 65-2299) an efficient and multiselective enzymatic step had been developed in which the easily accessible trans-1,3,5-triacetoxy-cyclohexane 5 was selectively monohydrolyzed excess (>99%) and yield (84%). Furthermore, for the synthesis of the enantiomer of 3, a simple and efficient enzymatic procedure for the asymmetric acetylation of cis-1,5-dihydroxy-3-(tert -butyldimethylsilanoxy)-cyclohexane 10 in an anhydrous organic solvent providing (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanoxy)-cyclohexane 11 in >99% ee and quantitative yield is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A process for the preparation of beta-hydroxy-delta-lactone using novel intermediates
  申请人：Council of Scientific & Industrial Research

  公开号：EP1234884B1

  公开（公告）日：2008-08-20
• Total Synthesis of (+)-Rugulosin and (+)-2,2′-epi-Cytoskyrin A through Cascade Reactions
  作者：K. C. Nicolaou、Yee Hwee Lim、Charles D. Papageorgiou、Jared L. Piper

  DOI：10.1002/anie.200503678

  日期：2005.12.9
• Total Syntheses of 2,2‘-<i>epi</i>-Cytoskyrin A, Rugulosin, and the Alleged Structure of Rugulin
  作者：K. C. Nicolaou、Yee Hwee Lim、Jared L. Piper、Charles D. Papageorgiou

  DOI：10.1021/ja0685708

  日期：2007.4.1

  The total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a more or less complete, cage-like structural motif termed "skyrane". The strategies developed for their total synthesis feature a cascade sequence called the "cytoskyrin cascade" and deliver these molecules in short order and in a stereoselective manner.