(1S,2R,5R,7S)-5-[(R)-2'-hydroxy-1'-phenyl-2'-propyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane | 444308-45-6

• 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)-5-[(R)-2'-hydroxy-1'-phenyl-2'-propyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
• 英文别名: (2R)-2-[(1S,2R,5R,7S,9R)-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecan-5-yl]-1-phenylpropan-2-ol
• CAS: 444308-45-6
• 化学式: C₂₀H₂₈O₂S
• 分子量: 332.507
• InChiKey: YFPZWZTUPDRTJV-DGYXETDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 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)-5-[(R)-2'-hydroxy-1'-phenyl-2'-propyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 在 N-氯代丁二酰亚胺 、 对甲苯磺酸 、 silver nitrate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 (1S,2R,7S)-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane
  参考文献：
  名称：

  Highly diastereoselective nucleophilic additions using a novel myrtenal-derived oxathiane as a chiral auxiliary

  摘要：

  The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected alpha-hydroxycarbonyl compounds in excellent enantiomeric excess. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00545-6
• 作为产物：
  描述：

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

  Highly diastereoselective nucleophilic additions using a novel myrtenal-derived oxathiane as a chiral auxiliary

  摘要：

  The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected alpha-hydroxycarbonyl compounds in excellent enantiomeric excess. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00545-6