(s)-1-(1'-Adamantyl)ethane-1,2-diol | 162005-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (s)-1-(1'-Adamantyl)ethane-1,2-diol
• 英文别名: (1S)-1-(1-adamantyl)ethane-1,2-diol
• CAS: 162005-34-7
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: WATQCEHAJJMVIS-LTMLNTECSA-N

物化性质

• 沸点：
  316.5±10.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (s)-1-(1'-Adamantyl)ethane-1,2-diol 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 (-)-1,3-bis<1'-(1-adamantyl)-2'-(triphenylmethyloxyethoxymethyl)>-2,5-dimethoxybenzene
  参考文献：
  名称：

  Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation

  摘要：

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.

  DOI：

  10.1016/0957-4166(94)80125-8
• 作为产物：
  描述：

  1-金刚烷乙酰氯 在 吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 水 、 双氧水 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 乙醚 、 叔丁醇 、 苯 为溶剂， 反应 86.0h， 生成 (s)-1-(1'-Adamantyl)ethane-1,2-diol
  参考文献：
  名称：

  Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation

  摘要：

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.

  DOI：

  10.1016/0957-4166(94)80125-8

文献信息

• Hirose, Keiji; Fuji, Junichi; Kamada, Kimiko, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 9, p. 1649 - 1657
  作者：Hirose, Keiji、Fuji, Junichi、Kamada, Kimiko、Tobe, Yoshito、Naemura, Koichiro

  DOI：——

  日期：——
• Catalytic asymmetric synthesis of new halogenated chiral synthons
  作者：Koen P. M. Vanhessche、K. Barry Sharpless

  DOI：10.1002/chem.19970030406

  日期：1997.4

  AbstractTwo‐step and practical asymmetric syntheses of enantiomerically pure 4‐trifluoromethyl‐2,2‐dioxo‐1,3,2‐dioxathiolane and 4‐trichloromethyl‐2,2‐dioxo‐1,3,2‐dioxathiolane (>98% ee) have been achieved. Catalytic asymmetric dihydroxylation (AD) of 3,3,3‐trifluoropropene and 3,3,3‐trichloropropene, respectively, is followed by direct cyclic sulfate formation by reaction with sulfuryl chloride. Opening of the cyclic sulfates with various nucleophiles provides easy access to important chiral synthons.
• Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation
  作者：Koichiro Naemura、Takashi Mizo-oku、Kimiko Kamada、Keiji Hirose、Yoshito Tobe、Masami Sawada、Yoshio Takai

  DOI：10.1016/0957-4166(94)80125-8

  日期：1994.8

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.