cis-ethyl 1-hydroxy-4-isopropylcyclohexanecarboxylate | 855303-69-4

• 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: cis-ethyl 1-hydroxy-4-isopropylcyclohexanecarboxylate
• CAS: 855303-69-4
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: GZKBFEAPHNBZPP-KLPPZKSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-ethyl 1-hydroxy-4-isopropylcyclohexanecarboxylate 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 336.0h， 生成 cis-(1-hydroxy-4-isopropylcyclohexyl)methyl 4-nitrobenzoate
  参考文献：
  名称：

  Stereoselective Synthesis ofcis-p-Menth-8-ene-1,7-diol,cis-p-Menthane-1,7-diol, andcis-p-Menthane-1,7,8-triol

  摘要：

  AbstractThe natural products cis‐p‐menthane‐1,7‐diol (cis‐IV), cis‐p‐menth‐8‐ene‐1,7‐diol (cis‐I) and cis‐p‐menthane‐1,7,8‐triol (cis‐II) are obtained starting from the corresponding cis‐cyanohydrins, cis‐2 and cis‐7, respectively, by chemical transformation of the cyano into the hydroxymethyl group. The key step of the synthesis is the very high cis‐selectivity (≥ 96 %) of the MeHNL‐catalyzed HCN addition to 4‐alkylcyclohexanones. From 4‐isopropylcyclohexanone (1) the cyanohydrin cis‐2 and from 4‐(1‐methylvinyl)cyclohexanone (6) the cyanohydrin cis‐7 result almost quantitatively. Regioselective hydroxylation of cis‐I affords the triol cis‐II. X‐ray crystal structure determinations of the final products confirm their cis‐configuration.

  DOI：

  10.1002/chem.200401147
• 作为产物：
  描述：

  4-异丙基环己酮 在 盐酸 、 氢氰酸 、 (S)-Me-hydroxynitrile lyase 、 nitrocellulose 作用下， 以 异丙醚 为溶剂， 反应 23.0h， 生成 cis-ethyl 1-hydroxy-4-isopropylcyclohexanecarboxylate
  参考文献：
  名称：

  Stereoselective Synthesis ofcis-p-Menth-8-ene-1,7-diol,cis-p-Menthane-1,7-diol, andcis-p-Menthane-1,7,8-triol

  摘要：

  AbstractThe natural products cis‐p‐menthane‐1,7‐diol (cis‐IV), cis‐p‐menth‐8‐ene‐1,7‐diol (cis‐I) and cis‐p‐menthane‐1,7,8‐triol (cis‐II) are obtained starting from the corresponding cis‐cyanohydrins, cis‐2 and cis‐7, respectively, by chemical transformation of the cyano into the hydroxymethyl group. The key step of the synthesis is the very high cis‐selectivity (≥ 96 %) of the MeHNL‐catalyzed HCN addition to 4‐alkylcyclohexanones. From 4‐isopropylcyclohexanone (1) the cyanohydrin cis‐2 and from 4‐(1‐methylvinyl)cyclohexanone (6) the cyanohydrin cis‐7 result almost quantitatively. Regioselective hydroxylation of cis‐I affords the triol cis‐II. X‐ray crystal structure determinations of the final products confirm their cis‐configuration.

  DOI：

  10.1002/chem.200401147