(1S,2R,5S)-(-)-cis-myrtanyl thiol

• 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: (1S,2R,5S)-(-)-cis-myrtanyl thiol
• 英文别名: [6,6-dimethylbicyclo[3.1.1]heptan-2-yl]methanethiol；(-)-cis-myrthanethiol；cis-myrtanethiol；((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methanethiol；[(1S,2R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methanethiol
• 化学式: C₁₀H₁₈S
• 分子量: 170.319
• InChiKey: KJBPNJMAGDDRRN-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S)-(-)-cis-myrtanyl thiol 在 二氧化氯 、 水 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以98%的产率得到[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl]methanesulfonic acid
  参考文献：
  名称：

  Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide

  摘要：

  cis-Myrtanethiol and a mixture of diastereoisomeric myrtanethiols were synthesized starting from (-)-beta-pinene. Their oxidation with chlorine dioxide afforded a number of derivatives such as disulfides, S-thiol-sulfonates, sulfonyl chlorides, and sulfonic acids. The effects of reaction conditions (solvent nature, reactant molar ratio, reaction time, catalyst) on the yield and ratio of the products were studied. The corresponding sulfonyl chloride was obtained in quantitative yield by oxidation of thiol in the presence of vanadyl acetyl-acetonate, and optimal conditions were found for quantitative formation of myrtanesulfonic acid.

  DOI：

  10.1134/s107042801910004x
• 作为产物：
  描述：

  (-)-顺式-桃金娘烷醇 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 生成 (1S,2R,5S)-(-)-cis-myrtanyl thiol
  参考文献：
  名称：

  Chirality transfer through sulfur or selenium to chiral propellers

  摘要：

  通过ECD方法和DFT计算，立体和电子效应对三苯甲基基团结构的手性转移的影响。

  DOI：

  10.1039/c5ra14072b

文献信息

• Potassium Channel Modulators
  申请人：Perez-Medrano Arturo

  公开号：US20120122890A1

  公开（公告）日：2012-05-17

  Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein G 1 , R 2 , R 1a , R 1b , X, X 1 , X 2 , X 3 , R x , J, k, n, q, and t are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了式（I）的KCNQ钾通道调节剂，其中G 1 ，R 2 ，R 1a ，R 1b ，X，X 1 ，X 2 ，X 3 ，R x ，J，k，n，q和t如规范中所定义。还描述了包含这些化合物的组合物；以及使用这些化合物和组合物治疗疾病和疾病的方法。
• The Use of Sulfides Derived from Carane, <i>P</i>-Menthane, Pinane, and Bornane in the Synthesis of Optically Active Epoxides
  作者：Anna Banach、Jacek Ścianowski、Piotr Ozimek

  DOI：10.1080/10426507.2013.819867

  日期：2014.1.1

  Abstract Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate

  摘要 开发了合成来自卡拉烷、对薄荷烷、蒎烷和冰片烷的光学活性甲基、苯基和二单萜基硫化物的便捷路线。通过相应的单萜硫醇盐与甲基碘或单萜甲苯磺酸盐的反应，已获得甲基和二单萜基硫化物。甲苯磺酸单萜与苯硫醇钠反应得到相应的苯基单萜硫化物。这些硫化物用于硫叶立德介导的反应以产生环氧化物。对于手性环氧化物的对映选择性合成，观察到高达 99:1 的良好非对映选择性和低至中等的对映选择性。图形概要
• Synthesis, structure determination and immobilization of some dirhodium complexes with chiral binding thiolato ligands. Investigation of their catalytic activity for enantioselective hydrogenation
  作者：Moris Eisen、Pnina Weitz、Sarah Shtelzer、Jochanan Blum、Herbert Schumann、Boris Gorella、Frank H. Görlitz

  DOI：10.1016/s0020-1693(00)80368-0

  日期：1991.10

  1 , a = 16.209(6), b = 14.150(5), c=9.899(3) A, Z = 2, R = 0.058, Rw = 0.094). Complex 5b was found to exist in the crystal as a pair of 1R,2R,5S- and 1S,2R,5S-epimers. Both chiral complexes have been immobilized by attachment to divinylbenzene-crosslinked polystyrene resins. Application of the chiral dirhodium complexes as catalysts for hydrogenation of methyl α-acetamidocinnamate revealed that while

  摘要（-）-顺[二羰基-μ-氯-[μ-6,6-二甲基双环[3.1.1]庚烷-2-甲硫基-S：S）]]双[三（1,1-二甲基乙基）膦]铑（5a）和（+）-顺-[二羰基-μ-氯-[μ-5β-甲基-2α-（1-甲基-乙基）环己烷硫基-S：S]]双[三（1,1-二甲基乙基） [Rh（CO）2] 2（μ-Cl）2，P（t-Bu）3和相应的硫化物（-）-顺式-（硫杂环丁烷）三甲基硅烷（4a）和（+）-（新庚烷硫基）三甲基硅烷（4b）。通过单晶X射线衍射确定5a和5b的分子结构（5a：C2221，a = 13.749（4），b = 23.509（9），c = 27.271（9）A，Z = 8，R = 0.0443，Rw ＝0.0491。5b：P 1，a ＝ 16.209（6），b ＝ 14.150（5），c ＝ 9.899（3）A，Z ＝ 2，R ＝ 0.058，Rw ＝ 0.094）。发现络合物5b以
• Potassium channel modulators
  申请人：Perez-Medrano Arturo

  公开号：US08609674B2

  公开（公告）日：2013-12-17

  Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein G1, R2, R1a, R1b, X, X1, X2, X3, Rx, J, k, n, q, and t are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了公式（I）的KCNQ钾通道调节剂，其中G1，R2，R1a，R1b，X，X1，X2，X3，Rx，J，k，n，q和t的定义如规范中所定义。还描述了包含这些化合物的组合物；以及使用这些化合物和组合物治疗疾病和病症的方法。
• Synthesis and Biological Activity of Unsymmetrical Monoterpenylhetaryl Disulfides
  作者：Denis V. Sudarikov、Yulia V. Gyrdymova、Alexander V. Borisov、Julia M. Lukiyanova、Roman V. Rumyantcev、Oksana G. Shevchenko、Diana R. Baidamshina、Nargiza D. Zakarova、Airat R. Kayumov、Ekaterina O. Sinegubova、Alexandrina S. Volobueva、Vladimir V. Zarubaev、Svetlana A. Rubtsova

  DOI：10.3390/molecules27165101

  日期：——

  New unsymmetrical monoterpenylhetaryl disulfides based on heterocyclic disulfides and monoterpene thiols were synthesized for the first time in 48–88% yields. Hydrolysis of disulfides with fragments of methyl esters of 2-mercaptonicotinic acid was carried out in 73–95% yields. The obtained compounds were evaluated for antioxidant, antibacterial, antifungal activity, cytotoxicity and mutagenicity.

  首次以 48-88% 的产率合成了基于杂环二硫化物和单萜硫醇的新型不对称单萜基杂芳基二硫化物。二硫化物与 2-巯基烟酸甲酯片段的水解以 73-95% 的产率进行。评价所得化合物的抗氧化、抗菌、抗真菌活性、细胞毒性和致突变性。