(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-cyclohex-2-enone | 1166841-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-cyclohex-2-enone
• 英文别名: (R)-5-(tert-butyldiphenylsilanyloxymethyl)-cyclohex-2-enone；(R)-5-(tert-butyldiphenylsilanyloxymethyl)cyclohex-2-enone；(5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]cyclohex-2-en-1-one
• CAS: 1166841-75-3
• 化学式: C₂₃H₂₈O₂Si
• 分子量: 364.56
• InChiKey: IDIWKTMVKGEOFV-LJQANCHMSA-N

物化性质

• 沸点：
  444.6±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-cyclohex-2-enone 在 sodium tetrahydroborate 、 甲基磺酰胺 、 cerium(III) chloride heptahydrate 、 AD-mix-β 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 27.0h， 生成 (1R,2R,3R,5R)-5-(hydroxymethyl)cyclohexane-1,2,3-triol
  参考文献：
  名称：

  Stereoselective synthesis of a novel natural carbasugar and analogues from hydroxymethylated cycloalkenone scaffolds

  摘要：

  Novel carbasugars from Streptomyces lincolnensis have been synthesized from an enantiomerically pure 5-hydroxymethyl-cyclohex-2-enone scaffold via a stereoselective approach. Several structural analogues of those carbasugars have also been synthesized in a stereoselective manner from hydroxymethylated cycloalkenone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.001
• 作为产物：
  描述：

  (R)-3-(tert-butyldiphenylsilanyloxymethyl)-hex-5-enenitrile 在 Grubbs catalyst first generation 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-cyclohex-2-enone
  参考文献：
  名称：

  Stereoselective synthesis of a novel natural carbasugar and analogues from hydroxymethylated cycloalkenone scaffolds

  摘要：

  Novel carbasugars from Streptomyces lincolnensis have been synthesized from an enantiomerically pure 5-hydroxymethyl-cyclohex-2-enone scaffold via a stereoselective approach. Several structural analogues of those carbasugars have also been synthesized in a stereoselective manner from hydroxymethylated cycloalkenone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.001

文献信息

• Chemo-enzymatic asymmetric total synthesis of penienone
  作者：Tridib Mahapatra、Rajib Bhunya、Samik Nanda

  DOI：10.1016/j.tetlet.2009.07.043

  日期：2009.9

  An asymmetric synthesis of penienone has been accomplished from (R)-5-hydroxymethyl-2-cyclohexenone by adopting a linear strategy. Lipase-PS-catalyzed enzymatic kinetic resolution (EKR) and Julia–Kocienski olefination followed by substrate-directed anionic hydroxymethylation have been successfully employed to achieve the target molecule.

  通过采用线性策略已经由（R）-5-羟甲基-2-环己烯酮完成了烯酮的不对称合成。脂肪酶-PS催化的酶动力学拆分（EKR）和Julia-Kocienski烯化反应，再与底物定向的阴离子羟甲基化反应已成功地用于实现目标分子。
• Asymmetric synthesis of palitantin by an enzymatic and organocatalytic approach
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2009.02.055

  日期：2009.3

  The natural enantiomer of the fungal metabolite (+)-palitantin has been synthesized by adopting a chemoenzymatic and organocatalytic approach. Lipase catalyzed kinetic resolution, Sharpless asymmetric dihydroxylation and organocatalytic asymmetric hydroxymethylation are the key steps involved in the total synthesis of the target molecule. (C) 2009 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2010.07.033

  日期：2010.9

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.