6-[(2R,4R,5R,6S)-4-Hydroxy-5-(2-methoxy-ethoxymethoxy)-6-methyl-piperidin-2-yl]-hexanoic acid methyl ester | 220023-72-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 6-[(2R,4R,5R,6S)-4-Hydroxy-5-(2-methoxy-ethoxymethoxy)-6-methyl-piperidin-2-yl]-hexanoic acid methyl ester
• 英文别名: methyl 6-[(2R,4R,5R,6S)-4-hydroxy-5-(2-methoxyethoxymethoxy)-6-methylpiperidin-2-yl]hexanoate
• CAS: 220023-72-3
• 化学式: C₁₇H₃₃NO₆
• 分子量: 347.452
• InChiKey: SSLHWVOVIFWGQU-KLZNWCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[(2R,4R,5R,6S)-4-Hydroxy-5-(2-methoxy-ethoxymethoxy)-6-methyl-piperidin-2-yl]-hexanoic acid methyl ester 在 氢氧化钾 、 三正丁基氢锡 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 6-(5-hydroxy-6-methylpiperidin-2-yl)hexanoic acid
  参考文献：
  名称：

  Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile

  摘要：

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01012-6
• 作为产物：
  描述：

  6-{(3R,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester 在 palladium dihydroxide 四丁基氟化铵 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 59.0h， 生成 6-[(2R,4R,5R,6S)-4-Hydroxy-5-(2-methoxy-ethoxymethoxy)-6-methyl-piperidin-2-yl]-hexanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile

  摘要：

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01012-6

文献信息

• Total synthesis of (+)-azimic acid, (+)-julifloridine, and proposed structure ofN-methyljulifloridine via cycloaddition of nitrone to a chiral dipolarophile
  作者：Toshiko Kiguchi、Mitsuko Shirakawa、Rina Honda、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(98)01012-6

  日期：1998.12

  A combination of 1,3-dipolar cycloaddition of Z-nitrones to the chiral dipolarophile and subsequent ring transformation of the resulting adducts to the piperidinols has provided a new practical synthesis of 2,6-disubstituted 3-piperidinol alkaloids, (+)-azimic acid, (+)-julifloridine, and the proposed structure of N-methyljulifloridine. (C) 1998 Elsevier Science Ltd. All rights reserved.