(S)-2-hydroxydecyl tosylate | 130202-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-hydroxydecyl tosylate
• 英文别名: [(2S)-2-hydroxydecyl] 4-methylbenzenesulfonate
• CAS: 130202-85-6
• 化学式: C₁₇H₂₈O₄S
• 分子量: 328.473
• InChiKey: UHMUNXMEITYUKV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxydecyl tosylate 在 lipase PS from Burkholderia cepacia 、 偶氮二甲酸二乙酯 作用下， 以 aq. phosphate buffer 、 甲苯 为溶剂， 反应 15.0h， 生成 (2R)-1-(Tosyloxy)decan-2-ol
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023
• 作为产物：
  描述：

  1,2-癸二醇 在 吡啶 、 lipase PS from Burkholderia cepacia 、 二异丁基氢化铝 、 二正丁基氧化锡 、 三乙胺 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 (S)-2-hydroxydecyl tosylate
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023

文献信息

• COMPOSITIONS AND METHODS OF USE
  申请人：Chitalia Vipul C.

  公开号：US20100209543A1

  公开（公告）日：2010-08-19

  This invention relates to the use of plant extracts, compositions thereof, and compounds isolated from plant extracts or obtained from synthetic means thereof, for the treatment of diseases, disorders or symptoms thereof (e.g., proliferation disorders, cancer).

  本发明涉及使用植物提取物、其组合物以及从植物提取物中分离或从合成手段中获得的化合物，用于治疗疾病、疾病症状或症状（例如增殖障碍、癌症）。
• Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion
  作者：Kazutsugu Matsumoto、Kazumasa Usuda、Hirokazu Okabe、Manabu Hashimoto、Yasutaka Shimada

  DOI：10.1016/j.tetasy.2012.11.023

  日期：2013.2

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.