(R)-(+)-N-allyl-3-piperidinylmethanol methanesulfonate | 131080-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-(+)-N-allyl-3-piperidinylmethanol methanesulfonate
• 英文别名: [(3R)-1-prop-2-enylpiperidin-3-yl]methyl methanesulfonate
• CAS: 131080-22-3
• 化学式: C₁₀H₁₉NO₃S
• 分子量: 233.332
• InChiKey: MACLXQFIJXTHGN-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-allyl-3-piperidinylmethanol methanesulfonate 在 盐酸 、 甲醇 、 Proton Sponge 、 1-氯乙基氯甲酸酯 、 sodium naphthalenide 、 magnesium 、 1,2-二溴乙烷 、 lithium bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 丙酮 为溶剂， 反应 29.5h， 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 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (R)-(+)-N-allyl-3-piperidinylmethanol methanesulfonate
  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

• MAGNUS, PHILIP;THURSTON, LEE S., J. ORG. CHEM., 56,(1991) N, C. 1166-1170
  作者：MAGNUS, PHILIP、THURSTON, LEE S.

  DOI：——

  日期：——
• US5220016A
  申请人：——

  公开号：US5220016A

  公开（公告）日：1993-06-15
• 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.