(R)-3-methoxycarbonyl-1-thio-4-azospire[4,5]decane | 302577-89-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-methoxycarbonyl-1-thio-4-azospire[4,5]decane
• 英文别名: (R)-3-methoxycarbonyl-1-thia-4-azaspiro[4.5]decane；methyl (3R)-1-thia-4-azaspiro[4.5]decane-3-carboxylate
• CAS: 302577-89-5
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: OHASBSLYWBCVJV-QMMMGPOBSA-N

物化性质

• 沸点：
  336.2±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二氯苯甲酰氯 、 (R)-3-methoxycarbonyl-1-thio-4-azospire[4,5]decane 以 甲苯 为溶剂， 反应 1.0h， 生成 methyl (R)-4-(2,4-dichlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

  摘要：

  通过活性子结构组合设计了一系列新型(R)-N-苯甲酰/二氯乙酰基-噻唑烷-4-羧酸甲酯。使用一锅法由L-半胱氨酸甲酯盐酸盐、酰氯和酮合成标题化合物。所有化合物均通过 IR、1H NMR、13C NMR 和 HRMS 进行表征。 4q的结构通过X射线晶体学测定。生物学试验表明，标题化合物在一定程度上保护玉米免受氯嘧磺隆的伤害。 ALS活性测定表明，标题化合物增加了受氯嘧磺隆抑制的玉米的ALS活性。分子对接模型表明，化合物4e与氯嘧磺隆竞争与除草剂靶酶活性位点结合，导致除草剂失效。

  DOI：

  10.3390/molecules23010155
• 作为产物：
  描述：

  环己酮 、 D-半胱氨酸甲酯盐酸盐 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 48.0h， 以63%的产率得到(R)-3-methoxycarbonyl-1-thio-4-azospire[4,5]decane
  参考文献：
  名称：

  Modular chiral thiazolidine catalysts in asymmetric aryl transfer reactions

  摘要：

  Modular chiral thiazolidine derivatives were synthesized in a single step from inexpensive and commercially available starting materials. These ligands catalyzed enantioselective arylation of different aldehydes using aryl boronic acids as a source of transferable aryl groups. The products were obtained in excellent yields and good enantioselectivities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.025

文献信息

• Novel thiazolidine derivatives as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
  作者：Qinglin Meng、Yuelan Li、Yan He、Yedi Guan

  DOI：10.1016/s0957-4166(00)00391-8

  日期：2000.11

  New chiral thiazolidine derivatives were synthesized conveniently from natural l-cysteine and showed good enantioselectivity (up to 90% ee) in the addition of diethylzinc to aldehydes. The catalytic efficiency of the thiazolidine derivatives is influenced by the different structures of the thiazolidine rings and the bulkiness of R moiety in the ester groups.

  新的手性噻唑烷衍生物可方便地从天然L-半胱氨酸合成，并且在将二乙基锌添加到醛中后显示出良好的对映选择性（最高90％ee）。噻唑烷衍生物的催化效率受噻唑烷环的不同结构和酯基团中R部分的体积的影响。
• The steric effect and enantioselectivity of chiral 2,2-disubstituted thiaprolinol derivatives as ligands for borane reduction of aromatic ketones and for diethylzinc addition to aromatic aldehydes
  作者：Hsiang-Ling Huang、Ya-Chuan Lin、Shyh-Fong Chen、Chia-Lin J. Wang、Lee Tai Liu

  DOI：10.1016/0957-4166(96)00399-0

  日期：1996.11

  chiral amino alcohols 3a-e has been prepared from natural amino acid L-cysteine. These compounds have been used as chiral ligands for borane reduction of ketones and for diethylzinc addition to aldehydes. In the reduction of ketones, 3b-e have been used as the substitute of (R)-prolinol to provide (S)-alcohols in good yields and modest enantioselectivity (30–50% ee). In the diethylzinc addition to aldehydes

  从天然氨基酸L-半胱氨酸制备了一系列新的手性氨基醇3a-e。这些化合物已用作手性配体，用于酮的硼烷还原和除醛以外的二乙基锌。在还原酮中，3b-e已被用作（R）-脯氨醇的替代品，以高收率和适度的对映选择性（30–50％ee）提供（S）醇。除醛中的二乙基锌外，3b-e以优异的产率和中等至良好的对映选择性（60-80％ee）促进了（S）醇的形成。
• Modular chiral thiazolidine catalysts in asymmetric aryl transfer reactions
  作者：Antonio Luiz Braga、Priscila Milani、Fabrício Vargas、Márcio W. Paixão、Jasquer A. Sehnem

  DOI：10.1016/j.tetasy.2006.10.025

  日期：2006.10

  Modular chiral thiazolidine derivatives were synthesized in a single step from inexpensive and commercially available starting materials. These ligands catalyzed enantioselective arylation of different aldehydes using aryl boronic acids as a source of transferable aryl groups. The products were obtained in excellent yields and good enantioselectivities. (c) 2006 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates
  作者：Li-Xia Zhao、Hao Wu、Yue-Li Zou、Qing-Rui Wang、Ying Fu、Chun-Yan Li、Fei Ye

  DOI：10.3390/molecules23010155

  日期：——

  A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, 1H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.

  通过活性子结构组合设计了一系列新型(R)-N-苯甲酰/二氯乙酰基-噻唑烷-4-羧酸甲酯。使用一锅法由L-半胱氨酸甲酯盐酸盐、酰氯和酮合成标题化合物。所有化合物均通过 IR、1H NMR、13C NMR 和 HRMS 进行表征。 4q的结构通过X射线晶体学测定。生物学试验表明，标题化合物在一定程度上保护玉米免受氯嘧磺隆的伤害。 ALS活性测定表明，标题化合物增加了受氯嘧磺隆抑制的玉米的ALS活性。分子对接模型表明，化合物4e与氯嘧磺隆竞争与除草剂靶酶活性位点结合，导致除草剂失效。