(+)-hygroline | 496-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+)-hygroline
• 英文别名: (2R)-1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-ol
• CAS: 496-47-9
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: CWMYODFAUAJKIV-HTQZYQBOSA-N

物化性质

• 熔点：
  33-34 °C
• 沸点：
  79 °C(Press: 11 Torr)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-Boc-四氢吡咯 在 lithium aluminium tetrahydride 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 21.08h， 生成 (+)-hygroline
  参考文献：
  名称：

  Total Synthesis of Hygrolines and Pseudohygrolines

  摘要：

  A concise two-step synthesis of all four diastereoisomeric hygrolines ((-)-hygroline (1), (+)-hygroline (2), (-)-pseudohygroline (3), (+)-pseudohygroline (4)) has been developed based on the (-)-sparteine (5)- or (+)-sparteine surrogate 11-mediated enantioselective lithiation of N-Boc pyrrolidine (6), followed by reaction of the chiral anion with (S)- or (R)-propylene oxide. Reduction of the resulting N-Boc amino alcohols furnished hygrolines and pseudohygrolines in 30% to 56% overall yields with dr's > 95:5.

  DOI：

  10.1021/jo4017343

文献信息

• New synthesis of all the four isomers of 2-(2-hydroxypropyl)pyrrolidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement
  作者：Hiroki Takahata、Minoru Kubota、Takefumi Momose

  DOI：10.1016/s0957-4166(97)00348-0

  日期：1997.8

  Both enantiomers of 2-(2-propenyl)pyrrolidine 7 (75–84% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 5, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)pyrrolidines 8 with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 8, of several 2-(2-hydroxypropyl)pyrrolidine alkaloids is demonstrated.

  通过末端烯烃5的不对称二羟基化（AD）制备的2-（2-丙烯基）吡咯烷7（75-84％ee）的两个对映体都进行第二次AD，以提供所有四个立体异构体2-（2-羟丙基）对映体增强（> 98％ee）的吡咯烷8。从8开始，证实了几种2-（2-羟丙基）吡咯烷生物碱的不对称合成。
• Synthese des Hygrolins. Zur Stereochemie des Hygrins und Cuskhygrins
  作者：F. Galinovsky、H. Zuber

  DOI：10.1007/bf00902780

  日期：——
• An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction
  作者：Shubhangi P. Bhoite、Rohit B. Kamble、Gurunath M. Suryavanshi

  DOI：10.1016/j.tetlet.2015.06.012

  日期：2015.8

  An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation. (C) 2015 Elsevier Ltd. All rights reserved.
• Total Synthesis of Hygrolines and Pseudohygrolines
  作者：Marc Liniger、Katja Estermann、Karl-Heinz Altmann

  DOI：10.1021/jo4017343

  日期：2013.11.1

  A concise two-step synthesis of all four diastereoisomeric hygrolines ((-)-hygroline (1), (+)-hygroline (2), (-)-pseudohygroline (3), (+)-pseudohygroline (4)) has been developed based on the (-)-sparteine (5)- or (+)-sparteine surrogate 11-mediated enantioselective lithiation of N-Boc pyrrolidine (6), followed by reaction of the chiral anion with (S)- or (R)-propylene oxide. Reduction of the resulting N-Boc amino alcohols furnished hygrolines and pseudohygrolines in 30% to 56% overall yields with dr's > 95:5.