methyl 2-<2->-2-hydroxy-3-<3-(N-allylpiperidinyl)>propionate | 131080-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-<2->-2-hydroxy-3-<3-(N-allylpiperidinyl)>propionate
• 英文别名: methyl 2-{2-[N-(phenylsulfonyl)indolyl]}-2-hydroxy-3-[3-(N-allylpiperidinyl)]propionate；methyl 2-[1-(benzenesulfonyl)indol-2-yl]-2-hydroxy-3-[(3S)-1-prop-2-enylpiperidin-3-yl]propanoate
• CAS: 131080-24-5；131080-25-6
• 化学式: C₂₆H₃₀N₂O₅S
• 分子量: 482.601
• InChiKey: JPWKMKDRBCAIHK-DQUNLGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-<2->-2-hydroxy-3-<3-(N-allylpiperidinyl)>propionate 在 盐酸 、 甲醇 、 Proton Sponge 、 1-氯乙基氯甲酸酯 、 sodium naphthalenide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 8.0h， 生成 (-)-(18'R)-4'-desethyl-4'-deshydroxy-7',8'-bisnorvinblastine
  参考文献：
  名称：

  Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine

  摘要：

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.

  DOI：

  10.1021/jo00003a045
• 作为产物：
  描述：

  ((R)-哌啶-3-基)甲醇 在 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 lithium bromide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 33.5h， 生成 methyl 2-<2->-2-hydroxy-3-<3-(N-allylpiperidinyl)>propionate
  参考文献：
  名称：

  Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine

  摘要：

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.

  DOI：

  10.1021/jo00003a045

文献信息

• Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine
  作者：Philip Magnus、Lee S. Thurston

  DOI：10.1021/jo00003a045

  日期：1991.2

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.