6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile | 544704-46-3

• 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: 6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile
• 英文别名: 2-[(2R,3S,6R)-6-methyl-3-phenylmethoxyoxan-2-yl]acetonitrile
• CAS: 544704-46-3
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: CNNGUUWOFPJSCO-VHDGCEQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 2H-Pyran-2-ethanol, tetrahydro-6-methyl-3-(phenylmethoxy)-, (3S,6R)-
  参考文献：
  名称：

  Synthesis of (+)-decarestrictine L

  摘要：

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00126-5
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 二异丁基氢化铝 、 对甲苯磺酸 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 82.0h， 生成 6-methyl-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-acetonitrile
  参考文献：
  名称：

  Synthesis of (+)-decarestrictine L

  摘要：

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00126-5

文献信息

• Synthesis of (+)-decarestrictine L
  作者：Julie M. Lukesh、William A. Donaldson

  DOI：10.1016/s0957-4166(03)00126-5

  日期：2003.3

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.