(1S,6S)-2,2-dimethyl-6-hydroxy-1-[3'-(1''-phenyl-1''H-tetrazole-5''-sulfanyl)butyl]-cyclohexane | 924884-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,6S)-2,2-dimethyl-6-hydroxy-1-[3'-(1''-phenyl-1''H-tetrazole-5''-sulfanyl)butyl]-cyclohexane
• CAS: 924884-82-2
• 化学式: C₁₉H₂₈N₄OS
• 分子量: 360.524
• InChiKey: GFUOELJLDYAUGX-XMKPYSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  63.83
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,6S)-2,2-dimethyl-6-hydroxy-1-[3'-(1''-phenyl-1''H-tetrazole-5''-sulfanyl)butyl]-cyclohexane 在 florisil 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以94%的产率得到(S)-2,2-dimethyl-1-[3'-(1''-phenyl-1''H-tetrazole-5''-sulfanyl)butyl]-6-oxocyclohexane
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015
• 作为产物：
  描述：

  (1S,6S)-2,2-dimethyl-1-(3'-hydroxybutyl)-6-methoxymethyloxycyclohexane 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 (1S,6S)-2,2-dimethyl-6-hydroxy-1-[3'-(1''-phenyl-1''H-tetrazole-5''-sulfanyl)butyl]-cyclohexane
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015