(R)-3-hydroxycyclopentanone | 109905-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-hydroxycyclopentanone
• 英文别名: 3-Hydroxycyclopentanon；Cyclopentanone, 3-hydroxy-, (R)-；(3R)-3-hydroxycyclopentan-1-one
• CAS: 109905-53-5
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: GULNLSGTYCQLLM-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxycyclopentanone 、 溴甲苯 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以83%的产率得到
  参考文献：
  名称：

  Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

  摘要：

  A straightforward approach to enantiomerically enriched (R) and (S)-3-hydroxycyclopentanone is described. The key step involves a kinetic resolution of racemic 3-hydroxycyclopentanone using commercial Pseudomonas cepacia lipase immobilized on diatomite (Amano lipase PS-DI). The absolute stereochemistry of the product was determined by derivatization into (R)-3-(benzyloxy)-cyclopentanone. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.09.015
• 作为产物：
  描述：

  1,3-环戊二醇 在 吡啶 、 sodium dichromate dihydrate 、 乙醇 、 硫酸 作用下， 以 甲基叔丁基醚 、 水 、 丙酮 为溶剂， 反应 42.67h， 生成 (R)-3-hydroxycyclopentanone
  参考文献：
  名称：

  Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

  摘要：

  A straightforward approach to enantiomerically enriched (R) and (S)-3-hydroxycyclopentanone is described. The key step involves a kinetic resolution of racemic 3-hydroxycyclopentanone using commercial Pseudomonas cepacia lipase immobilized on diatomite (Amano lipase PS-DI). The absolute stereochemistry of the product was determined by derivatization into (R)-3-(benzyloxy)-cyclopentanone. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.09.015

文献信息

• Enantioselective Michael Addition of Water
  作者：Bi-Shuang Chen、Verena Resch、Linda G. Otten、Ulf Hanefeld

  DOI：10.1002/chem.201405579

  日期：2015.2.9

  enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β‐hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium

  迄今为止，已证明使用水作为亲核试剂和溶剂的对映选择性迈克尔加成超出了合成化学家的能力。在此，描述了使用红球菌菌株的全细胞，在水中直接、对映选择性迈克尔加成水来制备重要的β-羟基羰基化合物。该方法获得了良好的产率和优异的对映选择性。氘标记研究表明迈克尔水合酶仅通过反立体化学催化水的添加。
• CROUT, DAVID H. G.;LEE, EDWARD R.;RATHBONE, DANIEL L., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1367
  作者：CROUT, DAVID H. G.、LEE, EDWARD R.、RATHBONE, DANIEL L.

  DOI：——

  日期：——
• Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution
  作者：Bi-Shuang Chen、Ulf Hanefeld

  DOI：10.1016/j.molcatb.2012.09.015

  日期：2013.1

  A straightforward approach to enantiomerically enriched (R) and (S)-3-hydroxycyclopentanone is described. The key step involves a kinetic resolution of racemic 3-hydroxycyclopentanone using commercial Pseudomonas cepacia lipase immobilized on diatomite (Amano lipase PS-DI). The absolute stereochemistry of the product was determined by derivatization into (R)-3-(benzyloxy)-cyclopentanone. (C) 2012 Elsevier B.V. All rights reserved.