(1S,2R,3S)-2-hyroxymethyl-6,6-dimethyl-3-thiobenzylbicyclo[3.1.1]heptane | 444308-36-5

• 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,3S)-2-hyroxymethyl-6,6-dimethyl-3-thiobenzylbicyclo[3.1.1]heptane
• CAS: 444308-36-5
• 化学式: C₁₇H₂₄OS
• 分子量: 276.443
• InChiKey: OKFGPVBDVAUFDY-UGUYLWEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S)-2-hyroxymethyl-6,6-dimethyl-3-thiobenzylbicyclo[3.1.1]heptane 在 sodium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 氨 、 苯 为溶剂， 反应 2.75h， 生成
  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：

  (1S,2R,3S)-2-formyl-6,6-dimethyl-3-thiobenzylbicyclo[3.1.1]heptane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.67h， 以96%的产率得到(1S,2R,3S)-2-hyroxymethyl-6,6-dimethyl-3-thiobenzylbicyclo[3.1.1]heptane
  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