Butyric acid (1R,2S)-2-(N'-tert-butoxycarbonyl-N-methyl-hydrazino)-cyclopentyl ester | 260392-37-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Butyric acid (1R,2S)-2-(N'-tert-butoxycarbonyl-N-methyl-hydrazino)-cyclopentyl ester
• 英文别名: [(1R,2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]cyclopentyl] butanoate
• CAS: 260392-37-8
• 化学式: C₁₅H₂₈N₂O₄
• 分子量: 300.398
• InChiKey: CECWYBOONZGLHD-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Butyric acid (1R,2S)-2-(N'-tert-butoxycarbonyl-N-methyl-hydrazino)-cyclopentyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到(1R,2S)-2-(N_β-t-butoxycarbonyl-N_α-methylhydrazino)cyclopentanol
  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：

  cis-2-methylaminocyclopentanol hydrochloride 在 sodium hydroxide 、 Pseudomonas cepacia lipase 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 异丙醚 为溶剂， 反应 33.5h， 生成 Butyric acid (1R,2S)-2-(N'-tert-butoxycarbonyl-N-methyl-hydrazino)-cyclopentyl ester
  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

文献信息

• Enzymatic resolution of (±)-2-(Nβ-t-butoxycarbonyl-Nα-methylhydrazino)cycloalkanols
  作者：Enikő Forró、Zsolt Szakonyi、Ferenc Fülöp

  DOI：10.1016/s0957-4166(99)00535-2

  日期：1999.12

  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.