(1R,4S)-camphor-10-thiol | 54984-43-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4S)-camphor-10-thiol
• 英文别名: 10-mercaptocamphor；d-camphor-10-thiol；camphor-10-thiol；(1R)-10-mercapto-bornan-2-one；(1R)-10-Mercapto-bornan-2-on；(1R,4S)-7,7-dimethyl-1-(sulfanylmethyl)bicyclo[2.2.1]heptan-2-one
• CAS: 54984-43-9；77026-99-4
• 化学式: C₁₀H₁₆OS
• 分子量: 184.302
• InChiKey: POWJRXPBPVKCAI-XVKPBYJWSA-N

物化性质

• 沸点：
  267.8±13.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.07
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trifluorothioacetyl chloride 、 (1R,4S)-camphor-10-thiol 以 氯仿 为溶剂， 反应 2.0h， 以82%的产率得到(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methyl trifluoroethanedithioate
  参考文献：
  名称：

  Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates

  摘要：

  A series of chiral S- or O-alkyl thionoesters have been synthesized by treatment of trifluorothioacetyl- or 2,2,3,3-tetrafluorothiopropionyl chloride with corresponding thiols or alcohols. The thia-Diels-Alder reaction of the thionoesters with symmetrical 1,3-dienes proceeds with diastereoselectivity up to 60%. Structures of cycloaddition products and corresponding transition states have been studied at the DFT level of approximation. The experimentally observed diastereomeric excess has been referred to differences in activation energies of transition states, preceding formation of the diastereomeric cycloaducts. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.011
• 作为产物：
  描述：

  左旋樟脑-10-磺酰氯 在 水 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (1R,4S)-camphor-10-thiol
  参考文献：
  名称：

  Ligand dependence of the synthetic approach and chiroptical properties of a magic cluster protected with a bicyclic chiral thiolate

  摘要：

  通过手性纯硫代醇稳定的手性金簇被制备、筛选并通过圆二色性和质谱进行表征。产品分布发现与配体有关。用樟脑硫醇保护的Au25簇在其与谷胱甘肽类似物的手性光学特性上表现出明显的相似性。

  DOI：

  10.1039/c2cc00056c

文献信息

• Reduction of Sulfonic Acids and Related Organosulfur Compounds with Triphenylphosphine–Iodine System
  作者：Shigeru Oae、Hideo Togo

  DOI：10.1246/bcsj.56.3802

  日期：1983.12

  excess iodine, however, these aliphatic sulfur compounds are converted eventually to the corresponding alkyl iodides. The relative reactivities of these sulfonyl derivatives in the reaction with the triphenylphosphine–iodine system are the following. Aromatic series: ArSO2Cl, ArSO2SAr′>ArSO2H>ArSO3R>ArSO3−HNBu3+ (or PyH+)>ArSO3H>ArSO2SO2Ar>>ArSO2CH2C(CH3)3, ArSO3Ar′. Aliphatic series: RSO2Cl, RSO2SR′,

  通过用三苯基膦和催化量的碘的混合物处理，芳烃磺酸、它们的钠盐和烷基芳烃磺酸盐可以很容易地还原成相应的芳烃硫醇，而烷烃磺酸、亚磺酸、二硫化物、硫代磺酸测试剂和磺酸盐也很容易类似地还原为相应的硫醇。然而，在用三苯基膦和过量碘的混合物处理后，这些脂肪族硫化合物最终转化为相应的烷基碘。这些磺酰基衍生物在与三苯基膦-碘体系反应中的相对反应性如下。芳族系列​​：ArSO2Cl、ArSO2SAr′>ArSO2H>ArSO3R>ArSO3−HNBu3+（或PyH+）>ArSO3H>ArSO2SO2Ar>>ArSO2CH2C(CH3)3、ArSO3Ar′。脂肪族系列：RSO2Cl、RSO2SR'、RSO2-HNBu3+>RSO3-HNBu3+>RSSR，RSO2H>RSO3H>RSH>RSO3R'。在这些反应中，带有供电子取代基的芳烃磺酸比具有供电子取代基的芳烃磺酸更容易被还原。
• Dimroth; Kraft; Aichinger, Justus Liebigs Annalen der Chemie, 1940, vol. 545, p. 124,133
  作者：Dimroth、Kraft、Aichinger

  DOI：——

  日期：——
• Ligand dependence of the synthetic approach and chiroptical properties of a magic cluster protected with a bicyclic chiral thiolate
  作者：Stefan Knoppe、Nuwan Kothalawala、Vijay Reddy Jupally、Amala Dass、Thomas Bürgi

  DOI：10.1039/c2cc00056c

  日期：——

  Chiral gold clusters stabilised by enantiopure thiolates were prepared, size-selected and characterised by circular dichroism and mass spectrometry. The product distribution is found to be ligand dependent. Au25 clusters protected with camphorthiol show clear resemblance of their chiroptical properties with their glutathionate analogue.

  通过手性纯硫代醇稳定的手性金簇被制备、筛选并通过圆二色性和质谱进行表征。产品分布发现与配体有关。用樟脑硫醇保护的Au25簇在其与谷胱甘肽类似物的手性光学特性上表现出明显的相似性。
• Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates
  作者：Vadim M. Timoshenko、Sergiy A. Siry、Alexander B. Rozhenko、Yuriy G. Shermolovich

  DOI：10.1016/j.jfluchem.2009.11.011

  日期：2010.2

  A series of chiral S- or O-alkyl thionoesters have been synthesized by treatment of trifluorothioacetyl- or 2,2,3,3-tetrafluorothiopropionyl chloride with corresponding thiols or alcohols. The thia-Diels-Alder reaction of the thionoesters with symmetrical 1,3-dienes proceeds with diastereoselectivity up to 60%. Structures of cycloaddition products and corresponding transition states have been studied at the DFT level of approximation. The experimentally observed diastereomeric excess has been referred to differences in activation energies of transition states, preceding formation of the diastereomeric cycloaducts. (C) 2009 Elsevier B.V. All rights reserved.