2-(2H-chromen-2-yl)propan-1-ol | 1394862-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(2H-chromen-2-yl)propan-1-ol
• 英文别名: (2S)-2-[(2R)-2H-chromen-2-yl]propan-1-ol
• CAS: 1394862-66-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: YHJZVUSEGNVNSW-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2H-chromen-2-yl)propanal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到2-(2H-chromen-2-yl)propan-1-ol
  参考文献：
  名称：

  Catalytic Asymmetric Addition of Aldehydes to Oxocarbenium Ions: A Dual Catalytic System for the Synthesis of Chromenes

  摘要：

  A synergistic catalytic system for the first asymmetric addition of aldehydes to in situ generated prochiral oxocarbenium ions has been developed. The dual catalytic protocol allows the simultaneous activation of both electrophile and nucleophile and provides access to a variety of valuable chiral 2H-chromenes with excellent enantioselectivities.

  DOI：

  10.1021/ol302084q

文献信息

• Catalytic Asymmetric Cross-Dehydrogenative Coupling of 2<i>H</i> -Chromenes and Aldehydes
  作者：Xinhui Pan、Xigong Liu、Shutao Sun、Zhilin Meng、Lei Liu

  DOI：10.1002/cjoc.201800369

  日期：2018.12

  The first catalytic asymmetric cross‐dehydrogenative coupling of 2H‐chromenes with aldehydes using o‐chloranil (3,4,5,6‐tetrachloro‐1,2‐ benzoquinone) as an oxidant has been described. The organocatalytic process is tolerated with a broad range of structurally and electronically varied 2H‐chromenes and aldehydes with good yield and high enantiocontrol.

  已经描述了使用邻氯苯甲腈（3,4,5,6-四氯-1,2-苯醌）作为氧化剂的2 H-色烯与醛的催化不对称交叉脱氢偶联反应。有机催化过程可耐受各种结构和电子形式的2 H-色烯和醛，具有良好的收率和较高的对映体控制能力。
• Catalytic Asymmetric Addition of Aldehydes to Oxocarbenium Ions: A Dual Catalytic System for the Synthesis of Chromenes
  作者：Magnus Rueping、Chandra M. R. Volla、Iuliana Atodiresei

  DOI：10.1021/ol302084q

  日期：2012.9.7

  A synergistic catalytic system for the first asymmetric addition of aldehydes to in situ generated prochiral oxocarbenium ions has been developed. The dual catalytic protocol allows the simultaneous activation of both electrophile and nucleophile and provides access to a variety of valuable chiral 2H-chromenes with excellent enantioselectivities.