(1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-2'-methyl-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane | 636599-75-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-2'-methyl-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
• 英文别名: (1S)-1-[(1S,2R,5R,7S,9R)-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecan-5-yl]-2-methyl-1-phenylpropan-1-ol
• CAS: 636599-75-2
• 化学式: C₂₁H₃₀O₂S
• 分子量: 346.534
• InChiKey: NPQOBUAJZZEHSO-CJGWPVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-2'-methyl-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 在 N-氯代丁二酰亚胺 、 silver nitrate 、 sodium tetrahydroborate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到(S)-3-methyl-2-phenylbutane-1,2-diol
  参考文献：
  名称：

  Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary

  摘要：

  The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.017
• 作为产物：
  描述：

  10-hydroxyisopinocampheylthiol 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 0.75h， 生成 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-2'-methyl-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
  参考文献：
  名称：

  Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary

  摘要：

  The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.017

文献信息

• Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary
  作者：Marı́a Elena Vargas-Dı́az、Luis Chacón-Garcı́a、Pedro Velázquez、Joaquı́n Tamariz、Pedro Joseph-Nathan、L.Gerardo Zepeda

  DOI：10.1016/j.tetasy.2003.07.017

  日期：2003.10

  The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee). (C) 2003 Elsevier Ltd. All rights reserved.