(2R,3S,6R)-2-Methyl-6-((S)-2-methyl-pentyl)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol | 375378-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (2R,3S,6R)-2-Methyl-6-((S)-2-methyl-pentyl)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol
• 英文别名: (2R,3S,6R)-2-methyl-6-[(2S)-2-methylpentyl]-1,1-dioxothian-3-ol
• CAS: 375378-13-5
• 化学式: C₁₂H₂₄O₃S
• 分子量: 248.387
• InChiKey: ZEAQLUGHZVTQHU-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3S,6R)-2-Methyl-6-((S)-2-methyl-pentyl)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol 在 吡啶 作用下， 反应 37.5h， 以51%的产率得到Acetic acid (2R,3S,6R)-2-methyl-6-((S)-2-methyl-pentyl)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl ester
  参考文献：
  名称：

  Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

  摘要：

  Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic beta-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into beta-hydroxysulfone in the presence of oxygen. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00654-3
• 作为产物：
  描述：

  hedathiosulfonic acid A 在 air 作用下， 反应 730.5h， 以0.22 g的产率得到(Z)-(6R,8S)-8-Methyl-undec-2-ene-6-sulfonic acid
  参考文献：
  名称：

  Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

  摘要：

  Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic beta-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into beta-hydroxysulfone in the presence of oxygen. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00654-3

文献信息

• Isolation and structures of hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum
  作者：Noboru Takada、Masami Watanabe、Kiyotake Suenaga、Kaoru Yamada、Masaki Kita、Daisuke Uemura

  DOI：10.1016/s0040-4039(01)01314-4

  日期：2001.9

  Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum, and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. Hedathiosulfonic acids exhibited acute toxicity. (C) 2001 Elsevier Science Ltd. All rights reserved.