1,1'-二羟基-3,3'-二己基二硫醚 | 344738-34-7

• 物质功能分类: 香精与香料 - 合成香料 - 硫醚类香料
• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 中文名称: 1,1'-二羟基-3,3'-二己基二硫醚
• 中文别名: 3,3’-二硫代双(1-己醇)
• 英文名称: 3,3'-disulfanediylbis(hexan-1-ol)
• 英文别名: 3,3'-disulfanediyldihexan-1-ol；3,3'-dithiobishexan-1-ol；3,3'-Dithiobis(1-hexanol)；3-(1-hydroxyhexan-3-yldisulfanyl)hexan-1-ol
• CAS: 344738-34-7
• 化学式: C₁₂H₂₆O₂S₂
• 分子量: 266.469
• InChiKey: KAPUPNHDWNOREH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-二羟基-3,3'-二己基二硫醚 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到3-propyl-1,2-oxathiolane-2-oxide
  参考文献：
  名称：

  Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines

  摘要：

  A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C6H12OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-gamma-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.

  DOI：

  10.1021/jf102022s
• 作为产物：
  描述：

  1-O-trimethylsilyloxy-3-hexanthiol 在 吡啶 作用下， 100.0 ℃ 、1.2 kPa 条件下， 反应 2.27h， 生成 1,1'-二羟基-3,3'-二己基二硫醚
  参考文献：
  名称：

  Elucidation of the 1,3-Sulfanylalcohol Oxidation Mechanism: An Unusual Identification of the Disulfide of 3-Sulfanylhexanol in Sauternes Botrytized Wines

  摘要：

  A four-step purification method was developed to isolate a citrus odorant detected by gas chromatography-olfactometry (GC-O), which was apparently specific to Sauternes botrytized wines. A fragmentation pattern of the odorant was obtained by multidimensional gas chromatography-mass spectrometry-olfactometry (MDGC-MS-O). The exact mass measurement was used to determine its elemental formula as C6H12OS. On the basis of these data, the unusual structure of 3-propyl-1,2-oxathiolane was synthesized and characterized for the first time. This confirmed its identification. Its occurrence in Sauternes wine extracts was demonstrated to result from the thermal oxidative degradation of 3-sulfanylhexanol disulfide (3,3'-disulfanediyldihexan-1-ol) in the GC injector. This disulfide was synthesized and then firmly identified for the first time in Sauternes wine. Although the presence of 3-sulfanylhexanol oxidation products had previously been reported in natural extracts (but not wine), the full oxidation pathway from 3-sulfanylhexanol to 3-propyl-gamma-sultine via 3,3'-disulfanediyldihexan-1-ol was clearly established for the first time. Because the disulfide has mainly been detected in Sauternes botrytized wines, this finding suggested a singular reactivity of 3-sulfanylhexanol in botrytized wines, thus opening up a wide range of new opportunities in wine chemistry.

  DOI：

  10.1021/jf102022s

文献信息

• Oxidation of 3-sulfanyl-alcohols with sodium metaperiodate: New synthesis of sultines
  作者：S. Yolka、R. Fellous、L. Lizzani-Cuvelier、M. Loiseau

  DOI：10.1016/s0040-4039(97)10757-2

  日期：1998.2

  A simple and highly efficient method for preparation of sultines by oxidation of 3-sulfanyl-alcohols with sodium metaperiodate is described.

  描述了一种简单高效的方法，该方法通过用偏高碘酸钠氧化3-硫烷基醇来制备磺胺类药物。
• DEGRADABLE POLYETHYLENE GLYCOL DERIVATIVE HAVING DISULFIDE LINKER
  申请人：NOF Corporation

  公开号：EP3604386A1

  公开（公告）日：2020-02-05

  To provide a degradable polyethylene glycol derivative in which polyethylene glycol chains are linked by a disulfide linker capable of accurately controlling the degradation rate under different reductive environments in the living body, and whose division rate into a polyethylene glycol chain of low molecular weight in the living body is able to be accurately controlled. A degradable polyethylene glycol derivative represented by formula (1). R1, R2, R3 and R4 represent each independently a hydrogen atom or a hydrocarbon group having from 1 to 6 carbon atoms, and at least one of R1, R2, R3 and R4 is the hydrocarbon group; P1 is a straight-chain or branched polyethylene glycol chain having a number of ethylene glycol units of 3 or more; P2 is a straight-chain polyethylene glycol chain having a number of ethylene glycol units of 3 or more; w is an integer of 1 to 8; u is an integer of 1 to 10; X1 is a chemically reactive functional group; and Z1, Z2 and Z3 are each independently a selected divalent spacer.

  提供一种可降解的聚乙二醇衍生物，其中的聚乙二醇链通过二硫连接剂连接，能够准确控制在生物体内不同还原环境下的降解速率，并且其在生物体内分裂成低分子量聚乙二醇链的速率能够得到准确控制。由式（1）表示的可降解聚乙二醇衍生物。R1、R2、R3 和 R4 各自独立地代表氢原子或具有 1 至 6 个碳原子的烃基，且 R1、R2、R3 和 R4 中至少有一个是烃基；P1 是乙二醇单元数为 3 或更多的直链或支链聚乙二醇链；P2 是具有 3 个或更多乙二醇单元的直链聚乙二醇链； w 是 1 至 8 的整数； u 是 1 至 10 的整数； X1 是化学活性官能团；以及 Z1、Z2 和 Z3 各自独立地是选定的二价间隔物。
• Degradable polyethylene glycol derivative having disulfide linker
  申请人：NOF CORPORATION

  公开号：US11220576B2

  公开（公告）日：2022-01-11

  A degradable polyethylene glycol derivative represented by formula (1). R1, R2, and R4 represent each independently a hydrogen atom or a hydrocarbon group having from 1 to 6 carbon atoms, and at least one of R1, R2, R3 and R4 is the hydrocarbon group; P1 is a straight-chain or branched polyethylene glycol chain having a number of ethylene glycol units of 3 or more; P2 is a straight-chain polyethylene glycol chain having a number of ethylene glycol units of 3 or more; w is an integer of 1 to 8; u is an integer of 1 to 10; X1 is a chemically reactive functional group; and Z1, Z2 and Z3 are each independently a selected divalent spacer.

  一种由式(1)表示的可降解聚乙二醇衍生物。R1、R2 和 R4 各自独立地代表氢原子或具有 1 至 6 个碳原子的烃基，且 R1、R2、R3 和 R4 中至少有一个是烃基；P1 是具有 3 个或更多乙二醇单元的直链或支链聚乙二醇链；P2 是具有 3 个或更多乙二醇单元的直链聚乙二醇链； w 是 1 至 8 的整数； u 是 1 至 10 的整数； X1 是化学活性官能团；以及 Z1、Z2 和 Z3 各自独立地是选定的二价间隔物。
• Samarium-Oxo/Hydroxy Cluster: A Solar Photocatalyst for Chemoselective Aerobic Oxidation of Thiols for Disulfide Synthesis
  作者：Lijun Wang、Lingxia Chen、Zixuan Qin、Bihan Zhao、Ke Ni、Hengzhao Li、Junyu Li、Hongxia Duan、Fazheng Ren、Jie An

  DOI：10.1021/acs.joc.4c00104

  日期：2024.6.21

  cluster (Sm-OC), via a unique auxiliary ligand-free oxidative hydrolysis. Using Sm-OC as catalyst, a solar photocatalyzed aerobic oxidation of thiols has been developed for the synthesis of valuable disulfides. Remarkably, this catalyst manifested a significant turnover number ≥2000 under tested conditions. Sm-OC-catalyzed aerobic oxidation showcased remarkable chemoselectivity. In thiol oxidations, despite

  氧化是化学工业中普遍存在的碳排放的第二个驱动因素。为了解决这个问题，光催化有氧氧化已成为一种有前途的替代方案。然而，实现令人满意的化学选择性和有效利用太阳光的挑战阻碍了该领域的进展。在此背景下，本研究通过独特的辅助无配体引入了一种新型均相光催化剂，[Sm 6 O(OH) 8 (H 2 O) 24 ]I 8 (H 2 O) 8簇(Sm-OC)氧化水解。使用Sm-OC作为催化剂，开发了一种硫醇的太阳能光催化有氧氧化方法，用于合成有价值的二硫化物。值得注意的是，该催化剂在测试条件下表现出≥2000 的显着周转数。 Sm-OC 催化的有氧氧化表现出显着的化学选择性。在硫醇氧化中，尽管二硫化物容易发生过度氧化，但在所有 28 种测试底物中均未检测到过度氧化副产物或非目标官能团的氧化。这项研究首次展示了镧系元素-氧/羟基簇在光催化中的应用。