2-amino-1-cyclohexyl-1,3-propanediol | 60204-66-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-1-cyclohexyl-1,3-propanediol
• 英文别名: (1RS,2RS)-2-amino-1-cyclohexyl-propane-1,3-diol；(1RS,2RS)-2-Amino-1-cyclohexyl-propan-1,3-diol；(1S,2S)-2-amino-1-cyclohexylpropane-1,3-diol
• CAS: 60204-66-2
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: DKAWCXNITOXQFI-IUCAKERBSA-N

物化性质

• 沸点：
  347.3±22.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Cyclohexyl-2-nitro-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol 在 镍 Amberlist 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 45.0~50.0 ℃ 、3.04 MPa 条件下， 反应 22.0h， 生成 2-amino-1-cyclohexyl-1,3-propanediol
  参考文献：
  名称：

  l-2-Nitro-1,3-alkanediols by stereoselective addition of nitroethanol to aldehydes. On the asymmetric electrophilic addition to double bonds

  摘要：

  DOI：

  10.1021/ja00298a033

文献信息

• Studies on Antibiotics and Related Substances. IV. Synthesis of DL-threo-β-Cyclohexylserine and DL-threo-2-Dichloroacetamido-1-cyclohexylpropane-1,3-diol
  作者：Sumio Umezawa、Yoshihisa Oguma

  DOI：10.1246/bcsj.29.987

  日期：1956.9

  When the N-acetyl ethyl ester of Erlenmeyer’s phenylserine was reduced with hydrogen over Raney nickel catalyst, ethyl DL-threo-N-acetyl-β-cyclohexylserinate was obtained in crude yields as high as 86.8 %. Subsequent hydrolysis with dilute hydrochloric acid afforded DL-threo-β-cyclohexylserine, which gave hexahydrobenzaldehyde by periodate oxidation. (2) Raney nickel reduction of ethyl DL-threo-β-cyclohexyl-serinate

  (1) Erlenmeyer苯丝氨酸的N-乙酰乙酯在阮内镍催化剂上用氢气还原，得到DL-苏式-N-乙酰-β-环己基丝氨酸乙酯，粗收率高达86.8%。随后用稀盐酸水解得到 DL-苏-β-环己基丝氨酸，通过高碘酸盐氧化得到六氢苯甲醛。(2) DL-threo-β-环己基丝氨酸乙酯的阮内镍还原得到DL-threo-2-amino-1-cyclohexylpropane-1, 3-diol。氨基醇被转化为 DL-threo-2-dichloroacetamido-1-cyclohexylpropane-1,3-diol，一种氯霉素类似物。
• Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile
  作者：Haitao Zhu、Pinhong Chen、Guosheng Liu

  DOI：10.1021/ja412023b

  日期：2014.2.5

  A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.