(1S,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclohexanol | 260392-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclohexanol
• 英文别名: tert-butyl N-[[(1S,2S)-2-hydroxycyclohexyl]-methylamino]carbamate
• CAS: 260392-51-6
• 化学式: C₁₂H₂₄N₂O₃
• 分子量: 244.334
• InChiKey: BBOFOELOLLDODU-UWVGGRQHSA-N

物化性质

• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclohexanol 在 Ra-Ni 三氟乙酸 、 氢气 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.42h， 生成 反式-(1R,2S)-2-甲氨基环己醇
  参考文献：
  名称：

  Enzymatic resolution of (±)-2-(Nβ-t-butoxycarbonyl-Nα-methylhydrazino)cycloalkanols

  摘要：

  Racemates of cis- and trans-2-(N-beta-t-butoxycarbonyl-N-alpha-methylhydrazino)cyclopentanols and -cyclohexanols 1-4 were resolved through lipase PS- or Novozym 435-catalysed asymmetric acylation of the secondary OH group at the (R)-stereogenic centre. High enantioselectivity (E >200) was observed when vinyl acetate or vinyl butyrate was used in diisopropyl ether, resulting in the enantiopure hydrazino esters 1a-4a and hydrazino alcohols 1b-4b. Methanolysis of the esters 1a-4a afforded the corresponding 2-hydrazinocycloalkanols 1c-4c (ee usually >95%). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00535-2
• 作为产物：
  描述：

  trans-2-methylaminocyclohexanol hydrochloride 在 sodium hydroxide 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.5h， 生成 (1S,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclohexanol
  参考文献：
  名称：

  Enzymatic resolution of (±)-2-(Nβ-t-butoxycarbonyl-Nα-methylhydrazino)cycloalkanols

  摘要：

  Racemates of cis- and trans-2-(N-beta-t-butoxycarbonyl-N-alpha-methylhydrazino)cyclopentanols and -cyclohexanols 1-4 were resolved through lipase PS- or Novozym 435-catalysed asymmetric acylation of the secondary OH group at the (R)-stereogenic centre. High enantioselectivity (E >200) was observed when vinyl acetate or vinyl butyrate was used in diisopropyl ether, resulting in the enantiopure hydrazino esters 1a-4a and hydrazino alcohols 1b-4b. Methanolysis of the esters 1a-4a afforded the corresponding 2-hydrazinocycloalkanols 1c-4c (ee usually >95%). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00535-2