cis-p-menthane-1,7-diol | 62790-18-5

• 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: cis-p-menthane-1,7-diol
• 英文别名: cis-1-(hydroxymethyl)-4-isopropylcyclohexane-1-ol
• CAS: 62790-18-5
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: JRXGXNRANYXDTK-AOOOYVTPSA-N

物化性质

• 熔点：
  89 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  284.5±8.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-p-menthane-1,7-diol 、 4-硝基苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 336.0h， 以92%的产率得到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 、 lithium aluminium tetrahydride 、 氢氰酸 、 (S)-Me-hydroxynitrile lyase 、 nitrocellulose 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 23.0h， 生成 cis-p-menthane-1,7-diol
  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

文献信息

• TRICYCLIC HETEROCYCLIC COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Babu Srinivasan

  公开号：US20110201593A1

  公开（公告）日：2011-08-18

  The invention provides novel compounds of formula I having the general formula: wherein R 1 , R 2 , R 3 , X and Y are as described herein. Accordingly, the compounds may be provided in pharmaceutically acceptable compositions and used for the treatment of immunological or hyperproliferative disorders.

  本发明提供了具有以下一般式的新化合物I： 其中R1、R2、R3、X和Y如本文所述。因此，这些化合物可以在药学上可接受的组合物中提供，并用于治疗免疫或过度增生性疾病。
• Stereoselective Synthesis ofcis-p-Menth-8-ene-1,7-diol,cis-p-Menthane-1,7-diol, andcis-p-Menthane-1,7,8-triol
  作者：Christoph Kobler、Franz Effenberger

  DOI：10.1002/chem.200401147

  日期：2005.4.22

  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.