(3R,4R)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-(Z)-1-butene-1-amine | 299908-88-6

• 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: (3R,4R)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-(Z)-1-butene-1-amine
• 英文别名: tert-butyl N-[(Z,3R,4R)-3-cyclohexyl-4-hydroxy-4-phenylbut-1-enyl]-N-(4-methoxyphenyl)carbamate
• CAS: 299908-88-6
• 化学式: C₂₈H₃₇NO₄
• 分子量: 451.606
• InChiKey: ZDIPKIWSCMJCHN-XRFXXKMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-(Z)-1-butene-1-amine 在 盐酸 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4R)-3-cyclohexyl-4-benzoxy-4-phenyl-butan-1-al
  参考文献：
  名称：

  Highly Enantioselective Syntheses of anti Homoaldol Products by (−)-Sparteine-Mediated Lithiation/Transmetalation/Substitution of N-Boc Allylic Amines

  摘要：

  [GRAPHICS](-)-Sparteine-mediated lithiation/transmetalation/substitution of N-Boc allylic amines provides anti-configured homoaldol precursors in yields of 38-85% and enantiomeric ratios of 83:17-99:1. Subsequent O-protection and hydrolysis allows access to O-protected homoaldol adducts in good yields. The absolute configurations of the homoaldol products have been assigned by calculation of optical rotations and by X-ray crystallography of derivatives. A stereochemical course of reaction for the lithiation/transmetalation/substitution sequence is proposed.

  DOI：

  10.1021/ol006186o
• 作为产物：
  描述：

  苯甲醛 、 N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-(E)-2-propene-1-amine 在 正丁基锂 、 鹰爪豆碱 、 titanium(IV) isopropylate 作用下， 以 various solvent(s) 为溶剂， 生成 (3S,4S)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-(Z)-1-butene-1-amine 、 (3R,4R)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-(Z)-1-butene-1-amine
  参考文献：
  名称：

  Highly Enantioselective Syntheses of anti Homoaldol Products by (−)-Sparteine-Mediated Lithiation/Transmetalation/Substitution of N-Boc Allylic Amines

  摘要：

  [GRAPHICS](-)-Sparteine-mediated lithiation/transmetalation/substitution of N-Boc allylic amines provides anti-configured homoaldol precursors in yields of 38-85% and enantiomeric ratios of 83:17-99:1. Subsequent O-protection and hydrolysis allows access to O-protected homoaldol adducts in good yields. The absolute configurations of the homoaldol products have been assigned by calculation of optical rotations and by X-ray crystallography of derivatives. A stereochemical course of reaction for the lithiation/transmetalation/substitution sequence is proposed.

  DOI：

  10.1021/ol006186o

文献信息

• Highly Enantioselective Syntheses of <i>anti</i> Homoaldol Products by (−)-Sparteine-Mediated Lithiation/Transmetalation/Substitution of <i>N</i>-Boc Allylic Amines
  作者：Marna C. Whisler、Louis Vaillancourt、Peter Beak

  DOI：10.1021/ol006186o

  日期：2000.8.1

  [GRAPHICS](-)-Sparteine-mediated lithiation/transmetalation/substitution of N-Boc allylic amines provides anti-configured homoaldol precursors in yields of 38-85% and enantiomeric ratios of 83:17-99:1. Subsequent O-protection and hydrolysis allows access to O-protected homoaldol adducts in good yields. The absolute configurations of the homoaldol products have been assigned by calculation of optical rotations and by X-ray crystallography of derivatives. A stereochemical course of reaction for the lithiation/transmetalation/substitution sequence is proposed.