(1R,2R)-2-methoxy-1-(4-methoxyphenyl)but-3-en-1-amine | 1449466-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2R)-2-methoxy-1-(4-methoxyphenyl)but-3-en-1-amine
• 英文别名: (1R,2R)-1-(4-methoxy-phenyl)-2-methoxy-3-butenamine
• CAS: 1449466-89-0
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: CCTGPWOOFSHIEI-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 盐酸 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (1S,2S)-2-methoxy-1-(4-methoxyphenyl)but-3-en-1-amine 、 (1R,2R)-2-methoxy-1-(4-methoxyphenyl)but-3-en-1-amine
  参考文献：
  名称：

  Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes

  摘要：

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.

  DOI：

  10.1021/ol900865y

文献信息

• Enantio- and diastereoselective synthesis of β-substituted-δ-aminoboronic esters from nitriles
  作者：P. Veeraraghavan Ramachandran、Wataru Mitsuhashi、Debanjan Biswas、Daniel R. Nicponski

  DOI：10.1016/j.tetlet.2013.06.076

  日期：2013.9

  The first stereocontrolled synthesis of the title δ-aminoboronic esters—proceeding from commercially available nitriles—via a reduction, Brown’s ‘allyl’ boration reaction, a Boc-protection, a hydroboration, an oxidative elimination of α-pinene, and an esterification reaction, has been reported in excellent enantio- and diastereoselectivities.

  通过还原，布朗的“烯丙基”硼酸化反应，Boc保护，氢硼化，α-pine烯的氧化消除和酯化反应，由市售的腈类化合物首次立体合成标题的δ-氨基硼酸酯。已经报道了优异的对映异构和非对映异构选择性。
• Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes
  作者：Lorell Muñoz-Hernández、John A. Soderquist

  DOI：10.1021/ol900865y

  日期：2009.6.18

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.