(-)-(2S)-Ruspolinone | 138664-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2S)-Ruspolinone
• 英文别名: (–)-ruspolinone；1-(3,4-dimethoxyphenyl)-2-[(2S)-pyrrolidin-2-yl]ethanone
• CAS: 138664-35-4
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: TYXKSMFICLVQCO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl 2-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(-)-(2S)-Ruspolinone
  参考文献：
  名称：

  A total synthesis of (−)-ruspolinone

  摘要：

  A synthesis of the pyrrolidine alkaloid (-)-ruspolinone (1) from (2S)-proline in 7 steps and 26% overall yield is presented which assigns the (2S) configuration to (-)-(1). The compound obtained by this route has [alpha]D-29.73-degrees compared to a value of zero for the material isolated from the plant suggesting racemisation had occurred during isolation.

  DOI：

  10.1016/s0040-4020(01)96170-8

文献信息

• Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal
  作者：Miguel Yus、Francisco Foubelo、Ana Sirvent、Sandra Hernández-Ibáñez

  DOI：10.1055/s-0037-1610763

  日期：2021.5

  efficient stereocontrolled preparation of 2-substituted pyrrolidines and 5-substituted indolizidin-7-ones, by using chiral N-tert-butanesulfinyl imines derived from 4-halobutanal as starting materials, is detailed. Addition of Grignard reagents and a decarboxylative Mannich­ reaction with β-keto acids involving these chiral imines proceeded with high diastereoselectivity. The synthesis of the pyrrolidinic

  详细介绍了通过使用衍生自4-卤代戊二醛的手性N-叔-丁烷亚磺酰基亚胺作为起始原料，有效地立体控制2-取代的吡咯烷和5-取代的吲哚齐丁-7-酮的方法。格氏试剂的添加以及涉及这些手性亚胺的β-酮酸与曼尼希的脱羧反应都具有很高的非对映选择性。吡咯烷类生物碱（–）-古古丁，（+）-维拉他敏B，（–）-去甲肾上腺素，反式-树醛神经碱和（-）-ruspolinone的合成证明了该方法的实用性。
• A total synthesis of (−)-ruspolinone
  作者：Keith Jones、King-Chung Woo

  DOI：10.1016/s0040-4020(01)96170-8

  日期：1991.8

  A synthesis of the pyrrolidine alkaloid (-)-ruspolinone (1) from (2S)-proline in 7 steps and 26% overall yield is presented which assigns the (2S) configuration to (-)-(1). The compound obtained by this route has [alpha]D-29.73-degrees compared to a value of zero for the material isolated from the plant suggesting racemisation had occurred during isolation.