5-chloro-4-nonanone | 138587-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-4-nonanone
• 英文别名: 5-Chlorononan-4-one
• CAS: 138587-52-7
• 化学式: C₉H₁₇ClO
• 分子量: 176.686
• InChiKey: VSNQQBFPRIIOTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  210.7±8.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-4-nonanone 在 Rhodotorula glutinis 、 水 作用下， 反应 6.0h， 生成 (-)-(4R,5S)-5-chloro-4-nonanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of α-halogeno-3-octanol and 4-or 5-nonanols. Application to the preparation of chiral epoxides

  摘要：

  A study of the microbiological reduction of different alpha-halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00470-4
• 作为产物：
  描述：

  三丁基硼 、 1-重氮-2-戊酮 在 N-氯代丁二酰亚胺 作用下， 生成 5-chloro-4-nonanone
  参考文献：
  名称：

  Chemoenzymatic synthesis of α-halogeno-3-octanol and 4-or 5-nonanols. Application to the preparation of chiral epoxides

  摘要：

  A study of the microbiological reduction of different alpha-halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00470-4

文献信息

• Highly diastereoselective synthesis of substituted epichlorohydrins and regioselective preparation of allyl alcohols using chloro or iodomethyllithium
  作者：JoséM. Concellón、Luján Llavona、Pablo L. Bernad

  DOI：10.1016/0040-4020(95)90943-q

  日期：1995.5

  Substituted epichlorohydrins 3 or 6 are obtained from α-bromo or α-chlorocarbonyl compounds (1 or 4) and chloro or iodomethyllithium, respectively. Starting from α-bromocarbonyl compounds 1 or acyclic α-chloro ketones the reaction takes place with total diastereoselectivity. Treatment of epichlorohydrins 3 or 6 with lithium iodide affords the same substituted allyl alcohols 7 in a regioselective manner

  取代的表氯醇3或6分别从α-溴或α-氯羰基化合物（1或4）和氯或碘甲基锂获得。从α-溴羰基化合物1或无环α-氯代酮开始，反应以完全非对映选择性进行。用碘化锂处理表氯醇3或6以区域选择性的方式提供相同的取代的烯丙醇7。提出了一种解释这种转变的机制。区域异构的烯丙醇11是通过表氯醇6与锂粉反应制备的。
• Barluenga, Jose; Llavona, Lujan; Yus, Miguel, Journal of the Chemical Society. Perkin transactions I, 1991, # 11, p. 2890
  作者：Barluenga, Jose、Llavona, Lujan、Yus, Miguel、Concellon, Jose M.

  DOI：——

  日期：——