(2S)-2-(hydroxymethyl)cycloheptan-1-one | 1186851-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-(hydroxymethyl)cycloheptan-1-one
• CAS: 1186851-01-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: KCAVOGZLZICBCH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 环庚酮 在 D-苏氨酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 97.0h， 以31%的产率得到(2S)-2-(hydroxymethyl)cycloheptan-1-one
  参考文献：
  名称：

  Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones

  摘要：

  Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric alpha-hydroxymethylations of cyclopentanone with aqueous formaldehyde have been developed, to furnish the corresponding alpha-(hydroxymethyl) cyclopentanone with high enantioselectivity. Further chemical transformation of alpha-(hydroxymethyl) cyclopentanone gave the key intermediate for jasmine lactone, which is widely found in fruits and flowers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.012

文献信息

• Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones
  作者：Nobuyuki Mase、Azusa Inoue、Masaki Nishio、Kunihiko Takabe

  DOI：10.1016/j.bmcl.2009.03.012

  日期：2009.7

  Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric alpha-hydroxymethylations of cyclopentanone with aqueous formaldehyde have been developed, to furnish the corresponding alpha-(hydroxymethyl) cyclopentanone with high enantioselectivity. Further chemical transformation of alpha-(hydroxymethyl) cyclopentanone gave the key intermediate for jasmine lactone, which is widely found in fruits and flowers. (C) 2009 Elsevier Ltd. All rights reserved.
• Direct asymmetric α-hydroxymethylation of ketones in homogeneous aqueous solvents
  作者：Monika Pasternak、Joanna Paradowska、Maria Rogozińska、Jacek Mlynarski

  DOI：10.1016/j.tetlet.2010.05.134

  日期：2010.8

  A chiral prolinamide-based zinc complex promotes the aldol reaction of ketones with aqueous formaldehyde, giving the corresponding adducts in good yields and high ees. The efficient direct aldol reaction of formaldehyde with ketones in homogeneous aqueous solution is presented for the first time. (C) 2010 Elsevier Ltd. All rights reserved.